From archerka@plu.edu Tue Apr 1 11:26:37 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id LAA26191 for ; Tue, 1 Apr 1997 11:26:36 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH6TV3CSAU008DY8@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 1 Apr 1997 11:23:17 PST Date: Tue, 01 Apr 1997 11:23:16 -0800 (PST) From: archerka@plu.edu Subject: Chapter 7 quiz To: organic chemistry list Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII There is going to be a chapter 7 quiz and that will be this Wednesday. He combined two days so we will only be studing chapter 7 this week. -Kristy From smithtw@plu.edu Tue Apr 1 12:05:18 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id MAA26675 for ; Tue, 1 Apr 1997 12:05:17 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH6V7U7NKW008O65@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 1 Apr 1997 12:01:52 PST Date: Tue, 01 Apr 1997 12:01:47 -0800 (PST) From: smithtw@plu.edu Subject: Re: Chapter 7 quiz In-reply-to: To: archerka@plu.edu Cc: organic chemistry list Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Then I assume that the learning group problem will be due on Friday as well then too, right? Tobin On Tue, 1 Apr 1997 archerka@plu.edu wrote: > > There is going to be a chapter 7 quiz and that will be this Wednesday. He > combined two days so we will only be studing chapter 7 this week. > -Kristy > > From kamperka@plu.edu Tue Apr 1 13:07:35 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id NAA27104 for ; Tue, 1 Apr 1997 13:07:34 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH6XE0SUIA008M68@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 1 Apr 1997 13:04:14 PST Date: Tue, 01 Apr 1997 13:04:06 -0800 (PST) From: kamperka@plu.edu Subject: Re: your mail In-reply-to: To: thomasbs@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII it attacks from the side opposite the leaving group in an SN2 rxn. On Thu, 27 Mar 1997 thomasbs@plu.edu wrote: > During an Sn2 reaction, which sidedoes the attacking electrons attack > from, or does it matter? A little clarification would be helpful. Thanx. > > From triplema@plu.edu Tue Apr 1 13:35:30 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id NAA27375 for ; Tue, 1 Apr 1997 13:35:28 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH6YDN4VOG006CUF@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 1 Apr 1997 13:32:00 PST Date: Tue, 01 Apr 1997 13:31:59 -0800 (PST) From: Harvey the Wonder Hamster Subject: lab 10 To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I need help with question #3 for lab 10. It asks why benzyl chloride reacts faster than 1-chlorobutane, even though both are primary alkyl chlorides. Any enlightenment would be appreciated. Thank you, Mark From triplema@plu.edu Tue Apr 1 13:42:53 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id NAA27454 for ; Tue, 1 Apr 1997 13:42:51 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH6YM4D3LY006CUF@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 1 Apr 1997 13:38:49 PST Date: Tue, 01 Apr 1997 13:38:48 -0800 (PST) From: Harvey the Wonder Hamster Subject: Lab #10 To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Hi. A couple of you guys had questions about exercise #1 for lab 10. Regardless of whether 2-bromobutane or 2-chlorobutane actually reacted in the lab, the book must think it was supposed to or it wouldn't have asked the question. I don't know exactly what the answer to the quesion is, but I think it has to do with the electronegativities and atomic radii of chlorine and bromine. If anybody out there knows the answer, I'd appreciate the help. Thank You, Mark From nelsonmj@plu.edu Tue Apr 1 15:18:04 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA28232 for ; Tue, 1 Apr 1997 15:18:03 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH71Y0OQWG008R07@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 1 Apr 1997 15:14:45 PST Date: Tue, 01 Apr 1997 15:14:42 -0800 (PST) From: nelsonmj@plu.edu Subject: Re: stereochemistry In-reply-to: To: youngcf@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Yes, a chiral and stereocenter are the same. On Thu, 20 Mar 1997 youngcf@plu.edu wrote: > > HELP: > > Is a chiral center the same as a stereocenter? I think it is, but I > want to be sure. > > Youngcf@plu.edu. > > From nelsonmj@plu.edu Tue Apr 1 15:44:33 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA28406 for ; Tue, 1 Apr 1997 15:44:32 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH72VK2MH4008R07@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 1 Apr 1997 15:41:04 PST Date: Tue, 01 Apr 1997 15:40:58 -0800 (PST) From: nelsonmj@plu.edu Subject: Re: Lab #10 In-reply-to: To: Harvey the Wonder Hamster Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII 2-bromobutane reacts faster then 2-chlorobutane because bromine is a better leaving group than chlorine. Bromine is a weaker base and therefore more stable then the chlorine. The bromine stabilizes its negative charge better. Since the it is more stable, this lowers the energy of activation and increases the rate of the reaction. Matt Nelson On Tue, 1 Apr 1997, Harvey the Wonder Hamster wrote: > > Hi. A couple of you guys had questions about exercise #1 for lab > 10. Regardless of whether 2-bromobutane or 2-chlorobutane actually reacted > in the lab, the book must think it was supposed to or it wouldn't have > asked the question. I don't know exactly what the answer to the quesion > is, but I think it has to do with the electronegativities and atomic radii > of chlorine and bromine. If anybody out there knows the answer, I'd > appreciate the help. > > Thank You, > Mark > > From nelsonmj@plu.edu Tue Apr 1 15:58:35 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA28531 for ; Tue, 1 Apr 1997 15:58:33 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH73D4N0WG008R07@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 1 Apr 1997 15:55:11 PST Date: Tue, 01 Apr 1997 15:55:08 -0800 (PST) From: nelsonmj@plu.edu Subject: Re: lab 10 In-reply-to: To: Harvey the Wonder Hamster Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Benzyl chloride reacts faster because benzyl chloride needs less energy to react. The benzyl ring has a higer potential energy due to electron delocalization and the therefore requires less of a push to react. Matt Nelson On Tue, 1 Apr 1997, Harvey the Wonder Hamster wrote: > > I need help with question #3 for lab 10. It asks why benzyl > chloride reacts faster than 1-chlorobutane, even though both are primary > alkyl chlorides. Any enlightenment would be appreciated. > > Thank you, > Mark > > From smithtw@plu.edu Tue Apr 1 16:21:35 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA28768 for ; Tue, 1 Apr 1997 16:21:33 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH746EJ3WK008K0P@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 1 Apr 1997 16:18:00 PST Date: Tue, 01 Apr 1997 16:17:56 -0800 (PST) From: smithtw@plu.edu Subject: Re: Lab #10 In-reply-to: To: nelsonmj@plu.edu Cc: Harvey the Wonder Hamster , organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Just for a little more help if it's still not clear, it's all in the book. Solomons, section 6.15E, page 256. It helps to read it and go through it. Tobin On Tue, 1 Apr 1997 nelsonmj@plu.edu wrote: > > 2-bromobutane reacts faster then 2-chlorobutane because bromine is a > better leaving group than chlorine. Bromine is a weaker base and > therefore more stable then the chlorine. The bromine stabilizes its > negative charge better. Since the it is more stable, this lowers the > energy of activation and increases the rate of the reaction. > Matt Nelson > > On Tue, 1 Apr 1997, Harvey the Wonder Hamster wrote: > > > > > Hi. A couple of you guys had questions about exercise #1 for lab > > 10. Regardless of whether 2-bromobutane or 2-chlorobutane actually reacted > > in the lab, the book must think it was supposed to or it wouldn't have > > asked the question. I don't know exactly what the answer to the quesion > > is, but I think it has to do with the electronegativities and atomic radii > > of chlorine and bromine. If anybody out there knows the answer, I'd > > appreciate the help. > > > > Thank You, > > Mark > > > > > > From taylormr@plu.edu Tue Apr 1 18:54:39 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id SAA29734 for ; Tue, 1 Apr 1997 18:54:37 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH79I2TFTC008BME@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 1 Apr 1997 18:50:57 PST Date: Tue, 01 Apr 1997 18:50:54 -0800 (PST) From: "M.Taylor" Subject: Re: lab 10 In-reply-to: To: Harvey the Wonder Hamster Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Mark, When benzyl chloride is treated with NaI in acetone, it reacts much faster than 1-chlorobutane, even though both compounds are primary alkyl chlorides. This is because the steric hindrance is greater on 1-chlorobutane. Hope this helps. Michele On Tue, 1 Apr 1997, Harvey the Wonder Hamster wrote: > > I need help with question #3 for lab 10. It asks why benzyl > chloride reacts faster than 1-chlorobutane, even though both are primary > alkyl chlorides. Any enlightenment would be appreciated. > > Thank you, > Mark > > From taylormr@plu.edu Tue Apr 1 18:56:31 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id SAA29786 for ; Tue, 1 Apr 1997 18:56:30 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH79KHIPM0008BME@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 1 Apr 1997 18:52:52 PST Date: Tue, 01 Apr 1997 18:52:50 -0800 (PST) From: "M.Taylor" Subject: Re: Lab #10 In-reply-to: To: Harvey the Wonder Hamster Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Mark, For question #1 in the lab, 2-bromobutane reacts faster than 2-chlorobutane because Bromine is a better leaving group than chlorine. Michele On Tue, 1 Apr 1997, Harvey the Wonder Hamster wrote: > > Hi. A couple of you guys had questions about exercise #1 for lab > 10. Regardless of whether 2-bromobutane or 2-chlorobutane actually reacted > in the lab, the book must think it was supposed to or it wouldn't have > asked the question. I don't know exactly what the answer to the quesion > is, but I think it has to do with the electronegativities and atomic radii > of chlorine and bromine. If anybody out there knows the answer, I'd > appreciate the help. > > Thank You, > Mark > > From taylormr@plu.edu Tue Apr 1 19:02:54 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id TAA29980 for ; Tue, 1 Apr 1997 19:02:53 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH79SHOAI8008BME@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 1 Apr 1997 18:59:20 PST Date: Tue, 01 Apr 1997 18:59:18 -0800 (PST) From: "M.Taylor" Subject: Re: your mail In-reply-to: To: thomasbs@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The nucleophile approaches the carbon bearing the leaving group from the backside, from the side directly opposite the leaving group. For further information, look on page 232 in Solomons. Hope this helps. Michele On Thu, 27 Mar 1997 thomasbs@plu.edu wrote: > During an Sn2 reaction, which sidedoes the attacking electrons attack > from, or does it matter? A little clarification would be helpful. Thanx. > > From fryhle@u.washington.edu Tue Apr 1 21:25:01 1997 Received: from jason04.u.washington.edu (jason04.u.washington.edu [140.142.78.5]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA00789 for ; Tue, 1 Apr 1997 21:25:00 -0800 Received: from homer23.u.washington.edu (homer23.u.washington.edu [140.142.77.3]) by jason04.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id VAA14028; Tue, 1 Apr 1997 21:21:47 -0800 Received: from localhost (fryhle@localhost) by homer23.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id VAA31622; Tue, 1 Apr 1997 21:21:47 -0800 Date: Tue, 1 Apr 1997 21:21:46 -0800 (PST) From: Craig Fryhle To: nelsonmj@plu.edu cc: Harvey the Wonder Hamster , organic1 Subject: Benzylic halides - Lab 10 In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings, all. I thought I'd better clarify a few things regarding this discussion. It is the characteristic of having the leaving group bonded to a carbon that is also bonded to a benzene ring that enhances both the SN1 and SN2 reactivity of benzylic halides. For SN1 reactions, a carbocation adjacent to a benzene ring is especially stable because the positive charge can be delocalized into the benzene ring. This can be shown by drawing resonance structures. For SN2 reactions the net negative charge of the transition state, where the nucleophile is partially bonded and the bond to the leaving group is partially broken, is also stabilized by the adjacent benzene ring. The orbitals of the transition state of the SN2 reaction can overlap with orbitals of the benzene ring in the case of benzylic substrates undergoing SN2 reactions. This lowers the energy of the transition state. One can't compare the potential energy of the reactants directly to rationalize the reactivity of these substrates. Rather, it is the relative difference in energy of activation for each reaction that influences the rate. This depends on the potential energy of the reactants and the energy of the transition state (i.e. the energy of activiation). CBF On Tue, 1 Apr 1997 nelsonmj@plu.edu wrote: > Benzyl chloride reacts faster because benzyl chloride needs less > energy to react. The benzyl ring has a higer potential energy due to > electron delocalization and the therefore requires less of a push to > react. > Matt Nelson > > On Tue, 1 Apr 1997, Harvey the Wonder Hamster wrote: > > > > > I need help with question #3 for lab 10. It asks why benzyl > > chloride reacts faster than 1-chlorobutane, even though both are primary > > alkyl chlorides. Any enlightenment would be appreciated. > > > > Thank you, > > Mark > > > > > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From fryhle@u.washington.edu Tue Apr 1 21:36:21 1997 Received: from jason03.u.washington.edu (jason03.u.washington.edu [140.142.77.10]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA00906 for ; Tue, 1 Apr 1997 21:36:20 -0800 Received: from homer23.u.washington.edu (homer23.u.washington.edu [140.142.77.3]) by jason03.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id VAA19640 for ; Tue, 1 Apr 1997 21:33:07 -0800 Received: from localhost (fryhle@localhost) by homer23.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id VAA22778 for ; Tue, 1 Apr 1997 21:33:07 -0800 Date: Tue, 1 Apr 1997 21:33:07 -0800 (PST) From: Craig Fryhle To: Organic Chemistry I List Subject: Re: Chapter 7 quiz In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings, all. To clarify the schedule, we will have the quiz on Chapter 7 on Wednesday 4/2 (tomorrow), the first day of class for Chapter 7. I think we may need three days on Chapter 7, so the Learning Group presentations for Ch 7 will be on Monday 4/7. We will still spend three days on Chapter 8, so we will not have the extra day I had designated as Review on the syllabus before the next exam. I'll have an office hour review session shortly before the exam instead. Welcome back. I hope you had a good spring break. CBF ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From petershm@plu.edu Tue Apr 1 22:33:16 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA01270 for ; Tue, 1 Apr 1997 22:33:14 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH7GTTJT00008D2G@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 1 Apr 1997 22:20:31 PST Date: Tue, 01 Apr 1997 22:20:26 -0800 (PST) From: petershm@plu.edu Subject: Re: your mail In-reply-to: To: jonesca@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII If it's a 1' 2' methyl etc. There is a chart in the book, I don't have the book right now or I would give you the pg #, sorry. HP On Fri, 28 Mar 1997 jonesca@plu.edu wrote: > what determines whether an sn2 reaction is going to go fast or slow? > > From fryhle@u.washington.edu Wed Apr 2 09:28:55 1997 Received: from jason04.u.washington.edu (jason04.u.washington.edu [140.142.78.5]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id JAA04908 for ; Wed, 2 Apr 1997 09:28:54 -0800 Received: from homer25.u.washington.edu (homer25.u.washington.edu [140.142.78.15]) by jason04.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id JAA13386 for ; Wed, 2 Apr 1997 09:25:40 -0800 Received: from localhost (fryhle@localhost) by homer25.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id JAA54716 for ; Wed, 2 Apr 1997 09:25:40 -0800 Date: Wed, 2 Apr 1997 09:25:39 -0800 (PST) From: Craig Fryhle To: Organic Chemistry I List Subject: Chapter 7 Learning Group Problem Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Learning Group Problems Chapter 7 ***** Groups 1,3,6 and 8 prepare to present parts I and III below. Groups 10, 11, 20, and 22 prepare to present parts II and IV below. ***** I. Write the structure of the product(s) from the reaction of 2-chloro-2,3-dimethylbutane when it is reacted with a) sodium ethoxide (NaOEt) in ethanol (EtOH) at 80 C, or (in a separate reaction) with potassium tert-butoxide (KOC(CH3)3) in tert-butanol (HOC(CH3)3) at 80 C. If more than one product is formed indicate which one would be expected to be the major one. Provide a detailed mechanism for formation of the major product from each reaction, including transition states. II. Explain using mechanistic arguments why the reaction of (2S)-2-bromo-1,2-diphenylpropane with sodium ethoxide (NaOEt) in ethanol (EtOH) at 80 C produces Z-1,2-diphenylpropene (none of the E diastereomer is formed). III. Write the structure of the product(s) formed when 1-methylcyclohexanol is reacted with 85% H3PO4 at 150 C. Write a detailed mechanism for the reaction. IV. Consider the reaction of 1-cyclobutylethanol (1-hydroxyethylcyclobutane) with conc. H2SO4 at 120 C. Write structures of all reasonable organic product(s). Assuming methylcyclopentene is one product, write a mechanism that accounts for its formation. Write mechanisms that account for formation of all other products, as well. lgp7-97.doc ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From fryhle@u.washington.edu Wed Apr 2 09:42:02 1997 Received: from jason05.u.washington.edu (jason05.u.washington.edu [140.142.78.6]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id JAA05037; Wed, 2 Apr 1997 09:41:59 -0800 Received: from homer25.u.washington.edu (homer25.u.washington.edu [140.142.78.15]) by jason05.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id JAA11470; Wed, 2 Apr 1997 09:38:46 -0800 Received: from localhost (fryhle@localhost) by homer25.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id JAA85574; Wed, 2 Apr 1997 09:38:45 -0800 Date: Wed, 2 Apr 1997 09:38:45 -0800 (PST) From: Craig Fryhle Reply-To: Craig Fryhle To: Organic Chemistry I List cc: Duane Swank , Brenda Tjelta , Dean Waldow Subject: tert-Pentyl Chloride Lab Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings. Here are the comments I mentioned in class today about this week's lab. 1) Determine the boiling point of your tert-pentyl chloride during the distillation step, as you have done before. Omit the microscale bp determination specified in the reaction protocol. 2) You will not run an IR spectrum on your own sample. Instead, interpret the IR spectrum printed in the text. Assign the principle absorption peaks of the spectrum (by their specific frequencies) to the specific aspects of the structure of tert-pentyl chloride from which they arise. CBF ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From LStandifer@msn.com Wed Apr 2 10:38:23 1997 Received: from upsmot03.msn.com (upsmot03.msn.com [204.95.110.85]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id KAA05524 for ; Wed, 2 Apr 1997 10:38:21 -0800 Received: from upmajb04.msn.com ([204.95.110.81]) by upsmot03.msn.com (8.6.8.1/Configuration 4) with SMTP id KAA10323 for ; Wed, 2 Apr 1997 10:29:45 -0800 Date: Wed, 2 Apr 97 03:33:43 UT From: "LeRoy Standifer" Message-Id: To: organic1 Subject: TOJC Lab #10 Questions Concerning the faster reactivity of 2-bromobutane than 2-chlorobutane, as I understand it, the bromine is more easily ionized in part because of steric hindrance, but also, for reasons still unclear to me, because the chlorine is more tightly bonded to the carbon atom than is the bromine. I think the difference in size and electronegativity between the chlorine and bromine has something to do with it. C. Krancich From crouthmr@plu.edu Wed Apr 2 10:53:15 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id KAA05671 for ; Wed, 2 Apr 1997 10:53:13 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH86YCC5LY009S7V@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 2 Apr 1997 10:48:37 PST Date: Wed, 02 Apr 1997 10:48:34 -0800 (PST) From: Sourcrout Subject: Exam no 2 To: Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII This request is really for Dr. Fryhle, but I should post it anyway. I wanted to inquire on behalf of a small handful of other students about the possibility of a study-guide regarding what reactions we should memorize for the exam. There is a plethera of methods and reactions throughout chapter 6 and 7 and Dr. Fryhle noted in today's lecture that we didn't need to know the method for a select couple. Although I would love to take the time to memorize all the reactions, I would prefer to fill my limited-capacity cortex with needed information if possible. Is this a reasonable request to ask what we need to know for the test? MC From weinmadj@plu.edu Wed Apr 2 10:57:30 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id KAA05707 for ; Wed, 2 Apr 1997 10:57:28 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH873852BA0090V3@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 2 Apr 1997 10:52:29 PST Date: Wed, 02 Apr 1997 10:52:28 -0800 (PST) From: weinmadj@plu.edu Subject: Lab 13 To: organic1 Cc: fryhle@u.washington.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I have a question for anyone that has done lab 13. Did anyone get a low yield? David From vogega@plu.edu Wed Apr 2 11:24:30 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id LAA05935 for ; Wed, 2 Apr 1997 11:24:29 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH883HU7V40096S7@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 2 Apr 1997 11:20:59 PST Date: Wed, 02 Apr 1997 11:20:56 -0800 (PST) From: vogega@plu.edu Subject: Re: Lab 13 In-reply-to: To: organic1, weinmadj@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII David- I did the lab yesterday and got an extremely low yield-only 12%. I don't where all of my product went. What did you get for the boiling point? Do you know what it should be? Mine was somewhere around 72 I think. Gretchen On Wed, 2 Apr 1997 weinmadj@plu.edu wrote: > > I have a question for anyone that has done lab 13. Did anyone get a low > yield? > > David > > From taylormr@plu.edu Wed Apr 2 14:13:33 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id OAA07212 for ; Wed, 2 Apr 1997 14:13:32 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH8DT4XP8W00996K@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 2 Apr 1997 14:05:09 PST Date: Wed, 02 Apr 1997 14:05:09 -0800 (PST) From: "M.Taylor" Subject: Lab 13 To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII This might sound like a stupid question, but for lab 13 do we do both experiment 13A and 13B? michele From petershm@plu.edu Wed Apr 2 15:11:32 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA07645 for ; Wed, 2 Apr 1997 15:11:30 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH8G07Y0HU009GP1@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 2 Apr 1997 15:07:23 PST Date: Wed, 02 Apr 1997 15:07:20 -0800 (PST) From: petershm@plu.edu Subject: Re: Lab 13 In-reply-to: To: "M.Taylor" Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII On the lab handout from the beginning of the year it says only part B, but I'm not completly sure, I only did the pre-lab for part B, so if I should have done part A can someone please let me know, thanks! HP On Wed, 2 Apr 1997, M.Taylor wrote: > > > This might sound like a stupid question, but for lab 13 do we do both > experiment 13A and 13B? > > michele > > > > From hodgedb@plu.edu Wed Apr 2 15:12:15 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA07672 for ; Wed, 2 Apr 1997 15:12:14 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH8G17LT4G0098YN@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 2 Apr 1997 15:08:13 PST Date: Wed, 02 Apr 1997 15:08:10 -0800 (PST) From: hodgedb@plu.edu Subject: Re: Lab 13 In-reply-to: To: "M.Taylor" Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Michele, We only have to do 13B: synthesis of tert-pentyl chloride. Dani On Wed, 2 Apr 1997, M.Taylor wrote: > > > This might sound like a stupid question, but for lab 13 do we do both > experiment 13A and 13B? > > michele > > > > From weinmadj@plu.edu Wed Apr 2 15:13:33 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA07697 for ; Wed, 2 Apr 1997 15:13:29 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH8G2O13BK0097V6@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 2 Apr 1997 15:09:22 PST Date: Wed, 02 Apr 1997 15:09:19 -0800 (PST) From: weinmadj@plu.edu Subject: Re: Lab 13 In-reply-to: To: vogega@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Gretchen, My yield was 11.6% and my boiling point was between 70 and 75. the actual boiling point is 85-86 degrees C. David On Wed, 2 Apr 1997 vogega@plu.edu wrote: > David- > I did the lab yesterday and got an extremely low yield-only 12%. > I don't where all of my product went. What did you get for the boiling > point? Do you know what it should be? Mine was somewhere around 72 I > think. > Gretchen > > On Wed, 2 Apr 1997 weinmadj@plu.edu wrote: > > > > > I have a question for anyone that has done lab 13. Did anyone get a low > > yield? > > > > David > > > > > > From hardinkm@plu.edu Wed Apr 2 17:44:47 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id RAA08630 for ; Wed, 2 Apr 1997 17:44:45 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH8DDKAKQ800964D@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 2 Apr 1997 13:52:50 PST Date: Wed, 02 Apr 1997 13:52:40 -0800 (PST) From: cancel Subject: Re: Meso Compound In-reply-to: To: schliema@plu.edu Cc: Organic Journal club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Mark- I think that 2,3-Dibromobutane itself, as an alkane, is considered a meso compound. Whether or not it is achiral depends on how it is drawn. In other words, it is superposable on it's mirror image depending on how the atoms are arranged around the stereocenter. So therefore, it's not just one enantiomer which is considered a meso compound, but the whole alkane itself, because of the way the atoms can be arranged. -Kate On Mon, 31 Mar 1997 schliema@plu.edu wrote: > On page 207, when the book describes what a Meso compound is, I'm not sure > I quite understand what the Meso compound is. What I mean is, are all 3 > of the molecules of 2,3-Dibromobutane called Meso compounds or is it just > the one molecule that is seperate from the other two in the book? The > book wasn't quite clear on this. So if anybody could help, please clarify > this for me. > > Thanks, > Mark > > > From steelecl@plu.edu Wed Apr 2 17:52:27 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id RAA08695 for ; Wed, 2 Apr 1997 17:52:25 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH8LKC3LZQ0096C1@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 2 Apr 1997 17:47:08 PST Date: Wed, 02 Apr 1997 17:47:07 -0800 (PST) From: steelecl@plu.edu To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I do not really understand the index of hydrogen deficiency. I do not understand what knowing the difference in pairs of hydrogens can help with. Can someone please explain this a little more clearly than the book does? Thanks Caroline From sounthna@plu.edu Wed Apr 2 20:34:25 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA09621 for ; Wed, 2 Apr 1997 20:34:23 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH8RA9LXXS0093WJ@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 2 Apr 1997 20:30:49 PST Date: Wed, 02 Apr 1997 20:30:47 -0800 (PST) From: sounthna@plu.edu Subject: Re: Lab 13 In-reply-to: To: "M.Taylor" Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII We just do 13B, the synthesis of tert-Butyl chloride. Nope On Wed, 2 Apr 1997, M.Taylor wrote: > > > This might sound like a stupid question, but for lab 13 do we do both > experiment 13A and 13B? > > michele > > > > From fryhle@u.washington.edu Wed Apr 2 21:35:50 1997 Received: from jason02.u.washington.edu (jason02.u.washington.edu [140.142.76.8]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA09999 for ; Wed, 2 Apr 1997 21:35:49 -0800 Received: from homer19.u.washington.edu (homer19.u.washington.edu [140.142.76.3]) by jason02.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id VAA10684; Wed, 2 Apr 1997 21:32:35 -0800 Received: from localhost (fryhle@localhost) by homer19.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id VAA39476; Wed, 2 Apr 1997 21:32:35 -0800 Date: Wed, 2 Apr 1997 21:32:35 -0800 (PST) From: Craig Fryhle To: cancel cc: schliema@plu.edu, Organic Journal club Subject: Re: Meso Compound In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Hi, all. I'd like to add a note of clarification about meso compounds. Regarding the example cited below, only the (2R,3S)-2,3-dibromobutane is a meso compound. It is the isomer that fits the criteria for meso compounds: 1) stereocenters are present, and 2) there is a mirror plane of symmetry between the stereocenters. The other two isomers of 2,3-dibromobutane are each one member of a pair of enantiomers - the 2R,3R enantiomer and the 2S,3S enantiomer (neither of these has a mirror plane of symmetry). I hope that helps. CBF On Wed, 2 Apr 1997, cancel wrote: > Mark- > I think that 2,3-Dibromobutane itself, as an alkane, is considered a meso > compound. Whether or not it is achiral depends on how it is drawn. In > other words, it is superposable on it's mirror image depending on how the > atoms are arranged around the stereocenter. So therefore, it's not just > one enantiomer which is considered a meso compound, but the whole alkane > itself, because of the way the atoms can be arranged. > -Kate > > On Mon, 31 Mar 1997 schliema@plu.edu wrote: > > > On page 207, when the book describes what a Meso compound is, I'm not sure > > I quite understand what the Meso compound is. What I mean is, are all 3 > > of the molecules of 2,3-Dibromobutane called Meso compounds or is it just > > the one molecule that is seperate from the other two in the book? The > > book wasn't quite clear on this. So if anybody could help, please clarify > > this for me. > > > > Thanks, > > Mark > > > > > > > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From sounthna@plu.edu Wed Apr 2 21:46:24 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA10132 for ; Wed, 2 Apr 1997 21:46:22 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH8RWL3NTK0093WJ@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 2 Apr 1997 20:48:53 PST Date: Wed, 02 Apr 1997 20:48:48 -0800 (PST) From: sounthna@plu.edu Subject: Re: your mail In-reply-to: To: steelecl@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The index of hydrogen deficiency is the number of hydrogen pairs that are missing( I don't know if that was a good word) when compared to the alkane. If you look at cyclohexene the molecular formula is C6H12 and if you compare it with its alkane, cyclohexane( C6H14), cyclohexene has 2 fewer hydrogens, so it has a index of hydrogen deficiency of 1. As for knowing what it can help us with I'm not totally sure either...so hopefully someone explains that. Hope it helps. Nope On Wed, 2 Apr 1997 steelecl@plu.edu wrote: > I do not really understand the index of hydrogen deficiency. I do not > understand what knowing the difference in pairs of hydrogens can help > with. Can someone please explain this a little more clearly than the book > does? Thanks > Caroline > > From callahnl@plu.edu Wed Apr 2 21:53:30 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA10211 for ; Wed, 2 Apr 1997 21:53:28 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IH8U10MVZA005TV1@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 2 Apr 1997 21:48:56 PST Date: Wed, 02 Apr 1997 21:48:51 -0800 (PST) From: "D'oh" Subject: Re: Meso Compound In-reply-to: To: cancel Cc: schliema@plu.edu, Organic Journal club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII hey Mark, A meso compound is a configuration of an achiral alkane with a stereocenter. The example discussed immediately below, 2,3-dibromobutane, is given in the book as four different stuctures. These structures are all mutually exclusive; just because one compound is meso does not mean that all the others will be. Page 208 in Solomons gives the easiest method of determining whether or not a compound is meso; this is by finding a plane of symmetry within the configuration. If a plane of symmetry is found, that particular configuration would be meso, which would not mean any others were. -nick On Wed, 2 Apr 1997, cancel wrote: > Mark- > I think that 2,3-Dibromobutane itself, as an alkane, is considered a meso > compound. Whether or not it is achiral depends on how it is drawn. In > other words, it is superposable on it's mirror image depending on how the > atoms are arranged around the stereocenter. So therefore, it's not just > one enantiomer which is considered a meso compound, but the whole alkane > itself, because of the way the atoms can be arranged. > -Kate > > On Mon, 31 Mar 1997 schliema@plu.edu wrote: > > > On page 207, when the book describes what a Meso compound is, I'm not sure > > I quite understand what the Meso compound is. What I mean is, are all 3 > > of the molecules of 2,3-Dibromobutane called Meso compounds or is it just > > the one molecule that is seperate from the other two in the book? The > > book wasn't quite clear on this. So if anybody could help, please clarify > > this for me. > > > > Thanks, > > Mark > > > > > > > > From fryhle@u.washington.edu Thu Apr 3 07:54:50 1997 Received: from jason03.u.washington.edu (jason03.u.washington.edu [140.142.77.10]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id HAA13451; Thu, 3 Apr 1997 07:54:49 -0800 Received: from homer32.u.washington.edu (homer32.u.washington.edu [140.142.70.19]) by jason03.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id HAA20662; Thu, 3 Apr 1997 07:51:35 -0800 Received: from localhost (fryhle@localhost) by homer32.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id HAA136430; Thu, 3 Apr 1997 07:51:34 -0800 Date: Thu, 3 Apr 1997 07:51:34 -0800 (PST) From: Craig Fryhle To: Organic Chemistry I List cc: Duane Swank , Brenda Tjelta , Sheri Tonn , Dean Waldow Subject: Dehydration of 4-Methylcyclohexanol (Chem 234) Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings, all. There will be no "variation" on this experiment, as noted in the syllabus. Simply perform the experiment as described in the lab text. The only clarifications are the following: 1) As before, measure the bp during the distillation step, rather than as a separate procedure. 2) In paragraph 4 of the procedure in Pavia, et al, a bent-tip Pasteur pipet is called for to rinse the walls of the Hickman still head. Instead of a bent-tip pipet use a regular Pasteur pipet and rinse as well as possible. 3) You should interpret the IR spectra for the reactant and product given in the lab text (as it pertains to Question 3.) You will not run your own IR's. and 4), You should do the tests for unsaturation specified in the protocol. NOTE: You should perform this experiment in a fume hood. The alkene product is particularly foul in odor. CBF ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From muellesb@plu.edu Thu Apr 3 18:14:18 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id SAA02378 for ; Thu, 3 Apr 1997 18:14:16 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHA0MC81B4009Z8G@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 3 Apr 1997 18:08:38 PST Date: Thu, 03 Apr 1997 18:08:37 -0800 (PST) From: Firefly Subject: lab To: Organic Chemlist Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII In determining bp, do we look for the first signs of boiling, or do we take the high point of the temp? From bowersmy@plu.edu Thu Apr 3 18:23:33 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id SAA02452 for ; Thu, 3 Apr 1997 18:23:32 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHA10761T200A4S8@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 3 Apr 1997 18:19:49 PST Date: Thu, 03 Apr 1997 18:19:48 -0800 (PST) From: bowersmy@plu.edu Subject: lab #13 To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII When determining boiling point watch the thermometer during distillation. The highest temp the thermometer reads during the distillation is the boiling point. From bekemj@plu.edu Thu Apr 3 20:39:16 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA03126 for ; Thu, 3 Apr 1997 20:39:15 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHA5QW7D1200A252@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 3 Apr 1997 20:35:51 PST Date: Thu, 03 Apr 1997 20:35:51 -0800 (PST) From: bekemj@plu.edu Subject: general question To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII In an Sn1 reaction, does the carbocation form due to K.E. of collision; or does the solvent actually take it away? Mike From bekemj@plu.edu Thu Apr 3 20:44:26 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA03190 for ; Thu, 3 Apr 1997 20:44:25 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHA5WYRUV000A252@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 3 Apr 1997 20:40:46 PST Date: Thu, 03 Apr 1997 20:40:45 -0800 (PST) From: bekemj@plu.edu Subject: general question To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII In an syn addition, 2 H are attached to the same side of a molecule. However, when this molecule forms it has a single bond which allows for free rotation. How can it still be a syn (same side reaction)? Mike From greenjn@plu.edu Thu Apr 3 22:05:28 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA03607 for ; Thu, 3 Apr 1997 22:05:26 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHA8PCW45C00A0L7@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 3 Apr 1997 22:00:13 PST Date: Thu, 03 Apr 1997 22:00:08 -0800 (PST) From: greenjn@plu.edu Subject: Sn2 reaction To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Going back to chapter 6, in section 6.7, what does it mean to be second order overall? From greenjn@plu.edu Thu Apr 3 22:12:59 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA03655 for ; Thu, 3 Apr 1997 22:12:58 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHA9022KZQ00A0L7@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 3 Apr 1997 22:08:46 PST Date: Thu, 03 Apr 1997 22:08:45 -0800 (PST) From: greenjn@plu.edu Subject: Sn2 vs E2 To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Even though this is something I should probably know by now, when Sn2 and E2 reactions compete, is the product entirely one or the other? Or is it a higher concentration of one and a lower concentration of another? From greenjn@plu.edu Thu Apr 3 22:24:03 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA03800 for ; Thu, 3 Apr 1997 22:24:02 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHA9DZ3WTO00A0L7@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 3 Apr 1997 22:19:59 PST Date: Thu, 03 Apr 1997 22:19:58 -0800 (PST) From: greenjn@plu.edu Subject: nucleophile To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Just a thought, in a larger molecule can a nucleophile attack elements other than carbon? Supposing the stereocenter is something such as oxygen, can Sn1 or Sn2 reactions still occur? Or are these reactions specific to carbon? From maschhjt@plu.edu Thu Apr 3 22:28:25 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA03848 for ; Thu, 3 Apr 1997 22:28:24 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHA9IV4KDS00A0N7@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 3 Apr 1997 22:24:08 PST Date: Thu, 03 Apr 1997 22:23:59 -0800 (PST) From: maschhjt@plu.edu Subject: Re: general question In-reply-to: To: organic1 , bekemj@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Mike, It is called syn addition because you are hydrogenating either a doubble or tripple bond, and as we know that these are both molicules that do not have free rotation. Therefore they can be attacked in either a syn, or an anti addition fassion. So the syn does not refer to the single bond conformation, but to which side of the doubble or tripple bond the hydrogens are added. I hope that this clears things up for you! Justin On Thu, 3 Apr 1997 bekemj@plu.edu wrote: > In an syn addition, 2 H are attached to the same side of a molecule. > However, when this molecule forms it has a single bond which allows for > free rotation. How can it still be a syn (same side reaction)? > > Mike > > From jonesca@plu.edu Thu Apr 3 23:37:11 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id XAA04338 for ; Thu, 3 Apr 1997 23:37:09 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHABW4A0KG0091HA@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 3 Apr 1997 23:31:53 PST Date: Thu, 03 Apr 1997 23:31:52 -0800 (PST) From: jonesca@plu.edu To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I must be retarteded but I think there is more than one sterocenter in problem 5.5 (limonene). The other stereocenters would be at either end of the double bond within the aromatic ring I think. If this is correct why are they showing only 1 stereocenter in the solutions manual? Does it have to be specified that they want trigonal planar also? From davidsct@plu.edu Fri Apr 4 00:01:18 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id AAA04815 for ; Fri, 4 Apr 1997 00:01:17 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHACSQQGL000A5Q5@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 3 Apr 1997 23:57:24 PST Date: Thu, 03 Apr 1997 23:57:24 -0800 (PST) From: davidsct@plu.edu Subject: ? To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII When dealing with the stabilities of Alkenes how do we determine which is more stable, a cis or trans alkene.? cd From davidsct@plu.edu Fri Apr 4 00:07:30 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id AAA04882 for ; Fri, 4 Apr 1997 00:07:29 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHAD10MYKQ00A5Q5@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 00:04:06 PST Date: Fri, 04 Apr 1997 00:04:04 -0800 (PST) From: davidsct@plu.edu Subject: Lost To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII this is a little vague of a question, but can anyone help explain the mechanism for the reduction of the synthesis of trans-alkenes on page 294 in Solomons? cd From carlisel@plu.edu Fri Apr 4 00:18:53 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id AAA05006 for ; Fri, 4 Apr 1997 00:18:51 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHADEO6D0K00AI7Z@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 00:15:10 PST Date: Fri, 04 Apr 1997 00:15:07 -0800 (PST) From: carlisel@plu.edu Subject: Cis Trans stability In-reply-to: To: davidsct@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII In lecture it was said that an E configuration is more stable than a Z. If you recall that a figure with an Z designation has the two groups of higher priority on the same side of the double bond. Therefore, a cis alkene would have a Z designation because no matter which was higher priority, the groups that were the same would be on the same side. Since an E is more stable then a Z, a trans is more stable than a cis. On Thu, 3 Apr 1997 davidsct@plu.edu wrote: > When dealing with the stabilities of Alkenes how do we determine which is > more stable, a cis or trans alkene.? > > cd > > From sounthna@plu.edu Fri Apr 4 00:18:54 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id AAA05010 for ; Fri, 4 Apr 1997 00:18:53 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHADEUXKIO009X01@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 00:15:16 PST Date: Fri, 04 Apr 1997 00:15:13 -0800 (PST) From: sounthna@plu.edu Subject: Re: ? In-reply-to: To: davidsct@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The trans is more stable than a cis of an alkene because there is more crowding or interaction when methyl groups let's say are on the same side. On Thu, 3 Apr 1997 davidsct@plu.edu wrote: > When dealing with the stabilities of Alkenes how do we determine which is > more stable, a cis or trans alkene.? > > cd > > From kamperka@plu.edu Fri Apr 4 09:44:59 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id JAA01271 for ; Fri, 4 Apr 1997 09:44:57 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHAX5M7QPS00AJWZ@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 09:40:34 PST Date: Fri, 04 Apr 1997 09:40:26 -0800 (PST) From: kamperka@plu.edu Subject: Re: Sn2 vs E2 In-reply-to: To: greenjn@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII It seems to me that the products will be a combination of the two types. Which will be the majority will depend on the nature of the base/nucleophile used. He gave an example in class today where the base was (CH3)3COK, a bulky base, and the major product was by the E1 reaction and the minor one was by the SN2 reaction. This is because bulky bases react mostly by E1 mechanisms, but can react by SN2 in the minority. Hope this makes sense -KK On Thu, 3 Apr 1997 greenjn@plu.edu wrote: > Even though this is something I should probably know by now, when Sn2 and > E2 reactions compete, is the product entirely one or the other? Or is it > a higher concentration of one and a lower concentration of another? > > From triplema@plu.edu Fri Apr 4 10:08:13 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id KAA01471 for ; Fri, 4 Apr 1997 10:08:12 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHAXYZC2TS00AQWE@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 10:04:06 PST Date: Fri, 04 Apr 1997 10:04:06 -0800 (PST) From: Harvey the Wonder Hamster Subject: lab 13 To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I was unable to finish the lab in one day and stopped after putting in my drying agent. I may not be able to finish until Monday. Will this be a problem? -Mark From fryhle@u.washington.edu Fri Apr 4 10:13:15 1997 Received: from jason03.u.washington.edu (jason03.u.washington.edu [140.142.77.10]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id KAA01577 for ; Fri, 4 Apr 1997 10:13:14 -0800 Received: from homer23.u.washington.edu (homer23.u.washington.edu [140.142.77.3]) by jason03.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id KAA16326; Fri, 4 Apr 1997 10:09:57 -0800 Received: from localhost (fryhle@localhost) by homer23.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id KAA56198; Fri, 4 Apr 1997 10:09:57 -0800 Date: Fri, 4 Apr 1997 10:09:57 -0800 (PST) From: Craig Fryhle To: Harvey the Wonder Hamster cc: organic1 Subject: Re: lab 13 - sample storage In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII There is the possibility that your product may evaporate if it is not stored in a very tightly sealed vial. CBF On Fri, 4 Apr 1997, Harvey the Wonder Hamster wrote: > > I was unable to finish the lab in one day and stopped after > putting in my drying agent. I may not be able to finish until Monday. Will > this be a problem? > -Mark > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From velezsa@plu.edu Fri Apr 4 10:14:48 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id KAA01604 for ; Fri, 4 Apr 1997 10:14:47 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHAY83C4E8009V95@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 10:10:47 PST Date: Fri, 04 Apr 1997 10:10:40 -0800 (PST) From: velezsa@plu.edu Subject: today's class To: "org. chem list" Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII In class today he wrote that if the bulky base was used you get a different product, but then he said one was the major product and one was the minor product. how can you get both of the products if they are from reactions with different bases. --SV From fryhle@u.washington.edu Fri Apr 4 10:15:53 1997 Received: from jason02.u.washington.edu (jason02.u.washington.edu [140.142.76.8]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id KAA01641 for ; Fri, 4 Apr 1997 10:15:53 -0800 Received: from homer23.u.washington.edu (homer23.u.washington.edu [140.142.77.3]) by jason02.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id KAA13340; Fri, 4 Apr 1997 10:12:37 -0800 Received: from localhost (fryhle@localhost) by homer23.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id KAA90836; Fri, 4 Apr 1997 10:12:37 -0800 Date: Fri, 4 Apr 1997 10:12:36 -0800 (PST) From: Craig Fryhle To: kamperka@plu.edu cc: greenjn@plu.edu, organic1 Subject: Re: Sn2 vs E2 In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII The reply below is a very helpful response. I would simply like to clarify that the elimination reactions that take place with strong bases (as we talked about in class today, e.g. EtONa and (CH3)3COK) react by E2 mechanisms, not E1 mechanisms. CBF On Fri, 4 Apr 1997 kamperka@plu.edu wrote: > > It seems to me that the products will be a combination of the two types. > Which will be the majority will depend on the nature of the > base/nucleophile used. He gave an example in class today where the base > was (CH3)3COK, a bulky base, and the major product was by the E1 reaction > and the minor one was by the SN2 reaction. This is because bulky bases > react mostly by E1 mechanisms, but can react by SN2 in the minority. > > Hope this makes sense > -KK > > On Thu, 3 Apr 1997 greenjn@plu.edu wrote: > > > Even though this is something I should probably know by now, when Sn2 and > > E2 reactions compete, is the product entirely one or the other? Or is it > > a higher concentration of one and a lower concentration of another? > > > > > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From velezsa@plu.edu Fri Apr 4 10:22:41 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id KAA01815 for ; Fri, 4 Apr 1997 10:22:40 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHAYI2REYE009V95@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 10:18:44 PST Date: Fri, 04 Apr 1997 10:18:43 -0800 (PST) From: velezsa@plu.edu Subject: example in class today To: "org. chem list" Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII he gave an example of a reaction of two different bases giving two different products, then he said one was the major product and one was the minor product depenting on which base was used. How can you get both products from the same reaction. --SV From triplema@plu.edu Fri Apr 4 10:24:54 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id KAA01844 for ; Fri, 4 Apr 1997 10:24:53 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHAYKYKSQE00AQWE@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 10:21:04 PST Date: Fri, 04 Apr 1997 10:21:03 -0800 (PST) From: Harvey the Wonder Hamster Subject: 7.8 To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Section 7.8 talks about the index of hydrogen deficiency. I think I know how to find the index of hydrogen deficiency for a given compound. However, the text mentions "molar equivalents" several times, and I am a little confused as to the meaning. -Harvey From bekemj@plu.edu Fri Apr 4 11:06:20 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id LAA02191 for ; Fri, 4 Apr 1997 11:06:17 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHB00E6C8G009W64@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 11:01:56 PST Date: Fri, 04 Apr 1997 11:01:44 -0800 (PST) From: bekemj@plu.edu Subject: Re: a little random, but... In-reply-to: To: Firefly Cc: Organic Chemlist Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII A neutron is vital to the stability of an atom. Because protons are positive and repel (exponentially with respect to their distance apart) the neutron (with a large, relative mass) spaces protons far enough apart to keep the positive nuclease together. This is, at least, what I came up with after ruminating about the subject. There is, however, the problem of what keeps the protons and neutrons together. The only force I can think of is gravitational. Although extremely small, the neutron and proton have a relatively large mass (compaired to an electron). Not having the mass of a neutron or proton available (and forgetting quite a lot of physics) I am not sure if this force would be enough to overcome the slight repulsive force between protons that would still exist in the positive center according to my model. Perhaps someone could offer further explanation regarding this discussion. Mike B. On Wed, 19 Mar 1997, Firefly wrote: > For about the last four years, I've been asking people if they know the > function/purpose of the neutron. As far as I know, no one knows, but I > thought that all of you bright new minds in chemistry might have some > hypotheses. > > -sbm > > > From davidsct@plu.edu Fri Apr 4 11:50:33 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id LAA02574 for ; Fri, 4 Apr 1997 11:50:33 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHB1KDPM2O00AOR5@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 11:46:56 PST Date: Fri, 04 Apr 1997 11:46:52 -0800 (PST) From: davidsct@plu.edu Subject: Re: Sn2 vs E2 In-reply-to: To: kamperka@plu.edu Cc: greenjn@plu.edu, organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII A couple of questions about the answer below What did Freyle mean by a bulky base, what is the defenition so to speak of a bulky base? ANd when -COK is written down does that stand for an Alkoxide? cd On Fri, 4 Apr 1997 kamperka@plu.edu wrote: > > It seems to me that the products will be a combination of the two types. > Which will be the majority will depend on the nature of the > base/nucleophile used. He gave an example in class today where the base > was (CH3)3COK, a bulky base, and the major product was by the E1 reaction > and the minor one was by the SN2 reaction. This is because bulky bases > react mostly by E1 mechanisms, but can react by SN2 in the minority. > > Hope this makes sense > -KK > > On Thu, 3 Apr 1997 greenjn@plu.edu wrote: > > > Even though this is something I should probably know by now, when Sn2 and > > E2 reactions compete, is the product entirely one or the other? Or is it > > a higher concentration of one and a lower concentration of another? > > > > > > From davidsct@plu.edu Fri Apr 4 12:19:31 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id MAA02821 for ; Fri, 4 Apr 1997 12:19:30 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHB2L4GMDC00AOR5@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 12:15:43 PST Date: Fri, 04 Apr 1997 12:15:43 -0800 (PST) From: davidsct@plu.edu Subject: IDH To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII In regards to the question about molar equivalents in section 7.8 when dealing with index of hydrogen deficiency. Molar equivalents just refers to the number of hydrogen pairs needed to either change from a single to a double or triple bond, or triple to a double or single bond (or any other order possible). But when you are going from a larger bond number to smaller you add molar equivalents, and when you go from a smaller bond number such as a single bond you subtract molar equivalents. Therefore when trying to go from an alkene to an alkane each double bond consumes one molar equivalent of hydrogen, or two hydrogens. And going from an alkyne to an alkane each triple bond consumes 2 molar equivalents, or 4 hydrogens. hope this isn't too confusing? I just have a hard time explaining it. cd From boothcj@plu.edu Fri Apr 4 12:43:49 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id MAA03035 for ; Fri, 4 Apr 1997 12:43:48 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHB3EK6XSI009XU6@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 12:39:35 PST Date: Fri, 04 Apr 1997 12:39:28 -0800 (PST) From: boothcj@plu.edu Subject: Re: Sn2 vs E2 In-reply-to: To: davidsct@plu.edu Cc: kamperka@plu.edu, greenjn@plu.edu, organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII A bulky base is one that has" steric hinderance". (CH3)3COK IS A large molecule and has steric hinderance. I'm not sure what the -COK is but I know that the K (potassium) separates from the O to form a free ion. On Fri, 4 Apr 1997 davidsct@plu.edu wrote: > A couple of questions about the answer below What did Freyle mean by a > bulky base, what is the defenition so to speak of a bulky base? ANd when > -COK is written down does that stand for an Alkoxide? > > cd > > On Fri, 4 Apr 1997 kamperka@plu.edu wrote: > > > > > It seems to me that the products will be a combination of the two types. > > Which will be the majority will depend on the nature of the > > base/nucleophile used. He gave an example in class today where the base > > was (CH3)3COK, a bulky base, and the major product was by the E1 reaction > > and the minor one was by the SN2 reaction. This is because bulky bases > > react mostly by E1 mechanisms, but can react by SN2 in the minority. > > > > Hope this makes sense > > -KK > > > > On Thu, 3 Apr 1997 greenjn@plu.edu wrote: > > > > > Even though this is something I should probably know by now, when Sn2 and > > > E2 reactions compete, is the product entirely one or the other? Or is it > > > a higher concentration of one and a lower concentration of another? > > > > > > > > > > > > From joelm@plu.edu Fri Apr 4 13:26:21 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id NAA03343 for ; Fri, 4 Apr 1997 13:26:17 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHB4XCV5B400AP1F@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 13:22:55 PST Date: Fri, 04 Apr 1997 13:22:51 -0800 (PST) From: super freak Subject: Re: Sn2 vs E2 In-reply-to: To: boothcj@plu.edu Cc: davidsct@plu.edu, kamperka@plu.edu, greenjn@plu.edu, organic1, ~joelm@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII does anyone know if the msds's are online yet? anyone know when they plan to be? thanks! lj ~~~~ joelm@plu.edu ~~~~ 'KISS ME BABY, I'M VACINATED!' --another crazy chic From nicholrc@plu.edu Fri Apr 4 15:05:56 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA04375 for ; Fri, 4 Apr 1997 15:05:54 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHB8ENG1OG009MTK@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 15:02:18 PST Date: Fri, 04 Apr 1997 15:02:17 -0800 (PST) From: nicholrc@plu.edu Subject: Forwarded mail.... To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII ---------- Forwarded message ---------- Date: Wed, 19 Mar 1997 14:51:36 -0800 (PST) From: nicholrc@plu.edu To: organic@rainier.chem.plu.edu Cc: nicholrc@plu.edu When and how does a carbon-halogen bond break? nicholrc@plu.edu From nicholrc@plu.edu Fri Apr 4 15:08:37 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA04414 for ; Fri, 4 Apr 1997 15:08:36 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHB8GVURRA009MTK@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 15:04:05 PST Date: Fri, 04 Apr 1997 15:04:05 -0800 (PST) From: nicholrc@plu.edu Subject: Forwarded mail.... To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII ---------- Forwarded message ---------- Date: Wed, 19 Mar 1997 14:54:21 -0800 (PST) From: nicholrc@plu.edu To: organic@rainier.chem.plu.edu Cc: nicholrc@plu.edu Can sodium (Na) act as a nucleophile? nicholrc@plu.edu From nicholrc@plu.edu Fri Apr 4 15:11:05 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA04447 for ; Fri, 4 Apr 1997 15:11:03 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHB8J0XQD8009MTK@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 15:05:48 PST Date: Fri, 04 Apr 1997 15:05:48 -0800 (PST) From: nicholrc@plu.edu Subject: Forwarded mail.... To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII ---------- Forwarded message ---------- Date: Fri, 21 Mar 1997 17:52:03 -0800 (PST) From: nicholrc@plu.edu To: organic@rainier.chem.plu.edu Cc: nicholrc@plu.edu We rotate the formula so that the groups with the lowest priority are directed away from us. But how do you know which groups have lower priority? nicholrc@plu.edu From nicholrc@plu.edu Fri Apr 4 15:11:16 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA04461 for ; Fri, 4 Apr 1997 15:11:15 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHB8LCHWWY009MTK@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 15:07:41 PST Date: Fri, 04 Apr 1997 15:07:41 -0800 (PST) From: nicholrc@plu.edu Subject: Forwarded mail.... To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII ---------- Forwarded message ---------- Date: Thu, 20 Mar 1997 15:50:21 -0800 (PST) From: nicholrc@plu.edu To: organic@rainier.chem.plu.edu Cc: nicholrc@plu.edu What does it mean to have a carbon that is Sp3 hybridized? nicholrc@plu.edu From wadecm@plu.edu Fri Apr 4 15:18:21 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA04573 for ; Fri, 4 Apr 1997 15:18:20 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHB8QIFV2800A18G@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 15:11:52 PST Date: Fri, 04 Apr 1997 15:11:51 -0800 (PST) From: wadecm@plu.edu Subject: Re: lab 13 In-reply-to: To: Harvey the Wonder Hamster Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII No it will not be a problem. I've done my lab on Monday before. On Fri, 4 Apr 1997, Harvey the Wonder Hamster wrote: > > I was unable to finish the lab in one day and stopped after > putting in my drying agent. I may not be able to finish until Monday. Will > this be a problem? > -Mark > > From wadecm@plu.edu Fri Apr 4 15:19:03 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA04615 for ; Fri, 4 Apr 1997 15:19:02 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHB8VC4TM000A18G@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 15:15:44 PST Date: Fri, 04 Apr 1997 15:15:44 -0800 (PST) From: wadecm@plu.edu Subject: reaction kinetics To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Can someone please explain second order reaction kinetics? From greenjn@plu.edu Fri Apr 4 15:24:13 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA04852 for ; Fri, 4 Apr 1997 15:24:07 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHB910H6PS00A6BM@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 15:20:19 PST Date: Fri, 04 Apr 1997 15:20:19 -0800 (PST) From: greenjn@plu.edu Subject: Re: your mail In-reply-to: To: jonesca@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I don't believe there can be a stereocenter in a trigonal planar molecule, so a molecule with a double bond cannot have a stereocenter. On Thu, 3 Apr 1997 jonesca@plu.edu wrote: > I must be retarteded but I think there is more than one sterocenter in > problem 5.5 (limonene). The other stereocenters would be at either end of > the double bond within the aromatic ring I think. If this is correct why > are they showing only 1 stereocenter in the solutions manual? Does it have > to be specified that they want trigonal planar also? > > From greenjn@plu.edu Fri Apr 4 15:26:12 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA04883 for ; Fri, 4 Apr 1997 15:26:11 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHB93E091400A6BM@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 15:22:14 PST Date: Fri, 04 Apr 1997 15:22:13 -0800 (PST) From: greenjn@plu.edu Subject: disubstituted alkynes To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Can someone please clarify what a disubstituted alkyne is? Thanks. From peeblere@plu.edu Fri Apr 4 15:41:39 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA05215 for ; Fri, 4 Apr 1997 15:41:38 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHB9NBQWTU00ACAZ@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 15:38:18 PST Date: Fri, 04 Apr 1997 15:38:18 -0800 (PST) From: peeblere@plu.edu Subject: lab 13 yeld To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Has anyone else obtained a product wieght <.05G? From peeblere@plu.edu Fri Apr 4 15:48:04 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA05436 for ; Fri, 4 Apr 1997 15:48:03 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHB9V9J1DA00ACAZ@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 15:44:42 PST Date: Fri, 04 Apr 1997 15:44:42 -0800 (PST) From: peeblere@plu.edu Subject: antbonding To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Could someone explan the dfference between antibonding and normal bondng? The tutors were not quite sure how to explain it wthout confusng me more. From brownak@plu.edu Fri Apr 4 15:56:23 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA05561 for ; Fri, 4 Apr 1997 15:56:22 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBA6JBUNK00AAAH@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 15:53:02 PST Date: Fri, 04 Apr 1997 15:53:01 -0800 (PST) From: brownak@plu.edu Subject: Re: activation energy In-reply-to: To: stensetj@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I am pretty sure that catalysts always lower the activation energy. In regards to catalysts affecting the products of the reaction, our text book talks about catalytic hydrogenation and that in this process, some of the catalysts used for hydrogenation convert some of the cis double bonds to the unnatural trans configuration -- p. 291. So yes, it seems that catalysts can affect the products of the reaction. On sunday, 30 March 1997 stensetj@plu.edu wrote: > Quick question, do catalysts always provide the reaction to proceed at a > lower actvation energy, and does the catalyst affect the products of the > reaction? > > From carlisel@plu.edu Fri Apr 4 15:56:29 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA05566 for ; Fri, 4 Apr 1997 15:56:28 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBA6NJ7GG00AF0B@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 15:53:07 PST Date: Fri, 04 Apr 1997 15:53:06 -0800 (PST) From: carlisel@plu.edu Subject: Re: lab 13 yeld In-reply-to: To: peeblere@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Yep! I am right there with you. My sample weight was very, very low. When I distilled it, there were only a few drops of distillate left. On Fri, 4 Apr 1997 peeblere@plu.edu wrote: > Has anyone else obtained a product wieght <.05G? > > > From triplema@plu.edu Fri Apr 4 15:59:34 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA05658 for ; Fri, 4 Apr 1997 15:59:33 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBAA268DS00AP20@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 15:55:52 PST Date: Fri, 04 Apr 1997 15:55:51 -0800 (PST) From: Harvey the Wonder Hamster Subject: Lab 13 To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII What WAS the purpose, as outlined in question 1, of washing the crude t-pentyl chloride with sodium bicarbonate? From brownak@plu.edu Fri Apr 4 16:02:05 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA05799 for ; Fri, 4 Apr 1997 16:02:04 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBADHUYDK00AAAH@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 15:58:38 PST Date: Fri, 04 Apr 1997 15:58:37 -0800 (PST) From: brownak@plu.edu Subject: Re: catalysts In-reply-to: To: holsinal@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Look on page 291 of the text, where it refers to catalytic hydrogenation -- It appears that the catalysts used for hydrogenation convert some of the cis double bonds to an unnatrual trans configuration. On Mon, 31 Mar 1997 holsinal@plu.edu wrote: > I know the main function of a catalyst, but do catalysts ever affect the > products of the reaction? > > From brownak@plu.edu Fri Apr 4 16:11:32 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA05977 for ; Fri, 4 Apr 1997 16:11:31 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBAP836IO00AAAH@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 16:08:06 PST Date: Fri, 04 Apr 1997 16:08:04 -0800 (PST) From: brownak@plu.edu Subject: Re: Lab 13 In-reply-to: To: weinmadj@plu.edu Cc: organic1, fryhle@u.washington.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Yes, it seems to be common. I only obtained .11 g of product, and a friend only obtained .o4g -- we have yet to fully understand why. On Wed, 2 Apr 1997 weinmadj@plu.edu wrote: > > I have a question for anyone that has done lab 13. Did anyone get a low > yield? > > David > > From peeblere@plu.edu Fri Apr 4 16:14:32 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA06068 for ; Fri, 4 Apr 1997 16:14:31 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBAT3BV0E00ACAZ@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 16:11:12 PST Date: Fri, 04 Apr 1997 16:11:11 -0800 (PST) From: peeblere@plu.edu Subject: Re: Lab 13 In-reply-to: To: "M.Taylor" Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII We were told to only do 13b. On Wed, 2 Apr 1997, M.Taylor wrote: > > > This might sound like a stupid question, but for lab 13 do we do both > experiment 13A and 13B? > > michele > > > > From brownak@plu.edu Fri Apr 4 16:17:00 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA06188 for ; Fri, 4 Apr 1997 16:16:59 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBAW4QHYI00AAAH@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 16:13:39 PST Date: Fri, 04 Apr 1997 16:13:38 -0800 (PST) From: brownak@plu.edu Subject: Re: lab In-reply-to: To: Firefly Cc: Organic Chemlist Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The highest temperature recorded during the distillation process should be the boiling point. On Thu, 3 Apr 1997, Firefly wrote: > In determining bp, do we look for the first signs of boiling, or do we > take the high point of the temp? > > > From peeblere@plu.edu Fri Apr 4 16:28:34 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA06357 for ; Fri, 4 Apr 1997 16:28:33 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBBA9ICJQ00ACAZ@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 16:25:03 PST Date: Fri, 04 Apr 1997 16:25:02 -0800 (PST) From: peeblere@plu.edu Subject: Re: Sn2 reaction In-reply-to: To: greenjn@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII In reference to your question, at the bottom of page 232 under the astrics sign states: The general overall order of a reaction is equal to the sum of the exponents a and b in the rate equation: Rate = k[A]a [B]b (a and b should be superscript) if in some other reaction, for example, we found that the Rate = k[A]2 [B] (2 is superscript) then we would say that the reaction is second order wth respect to [A], first order with respect to [B], and third order overall. Hope that helps. On Thu, 3 Apr 1997 greenjn@plu.edu wrote: > Going back to chapter 6, in section 6.7, what does it mean to be second > order overall? > > From brownak@plu.edu Fri Apr 4 16:33:03 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA06478 for ; Fri, 4 Apr 1997 16:33:01 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBBG0VF2Q00AAAH@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 16:29:43 PST Date: Fri, 04 Apr 1997 16:29:41 -0800 (PST) From: brownak@plu.edu Subject: Re: Forwarded mail.... In-reply-to: To: nicholrc@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Look at page 26--> in the text. The molecule is tetrahedral in shape with angles of 109.5. On Fri, 4 Apr 1997 nicholrc@plu.edu wrote: > > > ---------- Forwarded message ---------- > Date: Thu, 20 Mar 1997 15:50:21 -0800 (PST) > From: nicholrc@plu.edu > To: organic@rainier.chem.plu.edu > Cc: nicholrc@plu.edu > > > What does it mean to have a carbon that is Sp3 hybridized? > > nicholrc@plu.edu > > > From joelm@plu.edu Fri Apr 4 16:35:24 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA06510 for ; Fri, 4 Apr 1997 16:35:23 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBBIJ8N2O00AN5B@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 16:31:45 PST Date: Fri, 04 Apr 1997 16:31:42 -0800 (PST) From: super freak Subject: Re: lab 13 yeld In-reply-to: To: peeblere@plu.edu Cc: organic1, ~joelm@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII did anyone else get clumps on the side of your 3ml vial during the bicabonate step? i think it was that one anyhow. if i had been able to get them out of the vial, would it have increased my yield? or was it even a significant loss of product there? what do you guys think? thanks! lj ~~~~ joelm@plu.edu ~~~~ 'KISS ME BABY, I'M VACINATED!' --another crazy chic From joelm@plu.edu Fri Apr 4 16:40:14 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA06676 for ; Fri, 4 Apr 1997 16:40:13 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBBOLF8NS00AN5B@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 16:36:37 PST Date: Fri, 04 Apr 1997 16:36:36 -0800 (PST) From: super freak Subject: Re: lab 13 In-reply-to: To: wadecm@plu.edu Cc: Harvey the Wonder Hamster , organic1, ~joelm@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII i'm concerned about where all my product went! yes i know we all got a low yield. could some of it have evaporated from the distilation aparatus while i was waiting for it to cool ? gosh i hope not. =( lj ~~~~ joelm@plu.edu ~~~~ 'KISS ME BABY, I'M VACINATED!' --another crazy chic From joelm@plu.edu Fri Apr 4 16:44:54 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA06771 for ; Fri, 4 Apr 1997 16:44:53 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBBUQ7EZ600AN5B@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 16:41:33 PST Date: Fri, 04 Apr 1997 16:41:32 -0800 (PST) From: super freak Subject: Re: lab scoring In-reply-to: To: wadecm@plu.edu Cc: Harvey the Wonder Hamster , organic1, ~joelm@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII ok. who else is missing pnts for answers that are the same as someone else's but worded differently? same meaning but we stated it differently. ya know what i mean?? i'm concerned cuz it's happened to me a few times and i know it's happened to others too. lj ~~~~ joelm@plu.edu ~~~~ 'KISS ME BABY, I'M VACINATED!' --another crazy chic From peeblere@plu.edu Fri Apr 4 16:45:27 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA06917 for ; Fri, 4 Apr 1997 16:45:25 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBBV8MAK000ACAZ@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 16:41:57 PST Date: Fri, 04 Apr 1997 16:41:57 -0800 (PST) From: peeblere@plu.edu Subject: boiling point To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I may have already asked this, but this computer and I don't get along. My boiling point was 60 degrees, what should it have been? From wadecm@plu.edu Fri Apr 4 16:48:35 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA07013 for ; Fri, 4 Apr 1997 16:48:34 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBBYNKJDS00AKOA@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 16:44:48 PST Date: Fri, 04 Apr 1997 16:44:43 -0800 (PST) From: wadecm@plu.edu Subject: Re: Lab 13 In-reply-to: To: Harvey the Wonder Hamster Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I had the same question and was told that sodium bicarbonate was used to neutralize any remaining HCl acid and produced the CO2 that was vented out while shaking. On Fri, 4 Apr 1997, Harvey the Wonder Hamster wrote: > > What WAS the purpose, as outlined in question 1, of washing the > crude t-pentyl chloride with sodium bicarbonate? > > From gigraykc@plu.edu Fri Apr 4 17:32:26 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id RAA07403 for ; Fri, 4 Apr 1997 17:32:25 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBDIN02J800ACPH@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 17:29:04 PST Date: Fri, 04 Apr 1997 17:29:03 -0800 (PST) From: gigraykc@plu.edu Subject: Re: lab 13 In-reply-to: To: Harvey the Wonder Hamster Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII It might be a slight problem. I'm not sure if leaving the drying agent in will have any affect. But there may be some loss of your product due to evaporation. -kelli On Fri, 4 Apr 1997, Harvey the Wonder Hamster wrote: > > I was unable to finish the lab in one day and stopped after > putting in my drying agent. I may not be able to finish until Monday. Will > this be a problem? > -Mark > > From archerka@plu.edu Fri Apr 4 19:19:35 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id TAA08045 for ; Fri, 4 Apr 1997 19:19:34 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBH8UW5UA00B07H@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 19:15:43 PST Date: Fri, 04 Apr 1997 19:15:43 -0800 (PST) From: archerka@plu.edu Subject: Boiling Point To: organic chemistry list Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The real boiling point for t-pentyl chloride is 85-86 C. Of course since it's practically impossible to get a totally pure product, everyone's will be a little to a lot lower than that. -Kristy From archerka@plu.edu Fri Apr 4 19:24:08 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id TAA08152 for ; Fri, 4 Apr 1997 19:24:07 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBHEPZO4O00B07H@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 19:20:26 PST Date: Fri, 04 Apr 1997 19:20:25 -0800 (PST) From: archerka@plu.edu Subject: Lab 13 To: organic chemistry list Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I don't know if this was the problem for everyone who got really low yields for their product on Lab 13, but the stock room ran out of caps for the Hickman's stills and so we didn't get them in our basket. While distilling if it wasn't covered, some of your product could have come out that way. I almost forgot to put a piece of tinfoil on top of it. But that may not be the problem at all and if it isn't I'm completly baffled! -Kristy From petershm@plu.edu Fri Apr 4 19:44:22 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id TAA08348 for ; Fri, 4 Apr 1997 19:44:21 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBI4QWDJ000A7LV@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 19:40:41 PST Date: Fri, 04 Apr 1997 19:40:38 -0800 (PST) From: petershm@plu.edu Subject: Re: lab In-reply-to: To: brownak@plu.edu Cc: Firefly , Organic Chemlist Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII What kind of temps did you get? i got around 50 C. Is that even close? Thanks, HP On Fri, 4 Apr 1997 brownak@plu.edu wrote: > The highest temperature recorded during the distillation process should be > the boiling point. > > On Thu, 3 Apr 1997, Firefly wrote: > > > In determining bp, do we look for the first signs of boiling, or do we > > take the high point of the temp? > > > > > > > > From shorescf@plu.edu Fri Apr 4 20:05:40 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA08538 for ; Fri, 4 Apr 1997 20:05:38 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBIUCWDMO008B5W@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 20:01:18 PST Date: Fri, 04 Apr 1997 20:01:17 -0800 (PST) From: shorescf@plu.edu Subject: E1 and E2 reactions To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I was wondering how you could tell whether an alkyl halide is going to follow an E1 or an E2 pathway. Thanks Cas From smithtw@plu.edu Fri Apr 4 20:06:01 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA08543 for ; Fri, 4 Apr 1997 20:06:00 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBIVM749400AFO0@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 20:02:21 PST Date: Fri, 04 Apr 1997 20:02:17 -0800 (PST) From: smithtw@plu.edu Subject: Re: lab In-reply-to: To: petershm@plu.edu Cc: brownak@plu.edu, Firefly , Organic Chemlist Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I got a boiling temp of about 81 degrees C. I know that others got a boiling point around there too, but lower temps have been floating around and being asked about here in the e-mail. Tobin On Fri, 4 Apr 1997 petershm@plu.edu wrote: > What kind of temps did you get? i got around 50 C. Is that even close? > Thanks, HP > > On Fri, 4 Apr 1997 brownak@plu.edu wrote: > > > The highest temperature recorded during the distillation process should be > > the boiling point. > > > > On Thu, 3 Apr 1997, Firefly wrote: > > > > > In determining bp, do we look for the first signs of boiling, or do we > > > take the high point of the temp? > > > > > > > > > > > > > > > From shorescf@plu.edu Fri Apr 4 20:18:33 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA08726 for ; Fri, 4 Apr 1997 20:18:32 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBJBL1T86008B5W@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 20:15:11 PST Date: Fri, 04 Apr 1997 20:15:10 -0800 (PST) From: shorescf@plu.edu Subject: problem 7.5 To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Does anyone have any tips for determining the structural possibilities when given the hydrogen deficiency for an alkyl halide? Thanks, Cas From schelvac@plu.edu Fri Apr 4 21:41:06 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA09316 for ; Fri, 4 Apr 1997 21:41:05 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBM7NNF0400B24A@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 21:37:31 PST Date: Fri, 04 Apr 1997 21:37:31 -0800 (PST) From: schelvac@plu.edu Subject: SN1 and SN2 reactions To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I am still confused about the rate of formation of SN1 andSN2 reactions. How does one know which steps of the reaction will proceed quickly or slowly? How important is knowing the rate for SN1 reactions? Thanks, Alethea From velezsa@plu.edu Fri Apr 4 21:47:04 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA09436 for ; Fri, 4 Apr 1997 21:47:03 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBMF1AL9200AJS6@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 21:43:30 PST Date: Fri, 04 Apr 1997 21:43:28 -0800 (PST) From: velezsa@plu.edu Subject: Re: boiling point In-reply-to: To: peeblere@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I got 82 degrees --SV On Fri, 4 Apr 1997 peeblere@plu.edu wrote: > I may have already asked this, but this computer and I don't get > along. My boiling point was 60 degrees, what should it have been? > > From gigraykc@plu.edu Fri Apr 4 21:52:23 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA09534 for ; Fri, 4 Apr 1997 21:52:22 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBMLI72ZK00B1IK@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 21:48:52 PST Date: Fri, 04 Apr 1997 21:48:41 -0800 (PST) From: gigraykc@plu.edu Subject: Re: boiling point In-reply-to: To: peeblere@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I'm not sure what the correct boiling point should be but I got one a lot higher than yours. My boiling point was 81 degrees. I was just wondering if anyone does know what the correct boiling point is? -kelli On Fri, 4 Apr 1997 peeblere@plu.edu wrote: > I may have already asked this, but this computer and I don't get > along. My boiling point was 60 degrees, what should it have been? > > From schelvac@plu.edu Fri Apr 4 21:55:01 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA09567 for ; Fri, 4 Apr 1997 21:55:00 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBMOBLO7U00B24A@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 21:50:57 PST Date: Fri, 04 Apr 1997 21:50:57 -0800 (PST) From: schelvac@plu.edu Subject: Learning Group Chapter 7 To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII In the reactions discussed in problem 1, with regards to 2-chloro-2,3-dimethylbutane, how does one know the best place for the sodium ethoxide to react with the 2-chloro-2,3-dimethylbutane? By this I mean how do you know which product is going to be the most stable and abundant? Thanks, Alethea From gigraykc@plu.edu Fri Apr 4 22:00:01 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA09735 for ; Fri, 4 Apr 1997 22:00:00 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBMV5JV4C00B1IK@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 21:56:27 PST Date: Fri, 04 Apr 1997 21:56:27 -0800 (PST) From: gigraykc@plu.edu Subject: SN vs. EN To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I was just wondering what makes a compound undergo a sythesis or elimination reaction? And how does the compound "choose" which of the two reaction pathways it will take?-thanks -kelli From schelvac@plu.edu Fri Apr 4 22:00:23 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA09762 for ; Fri, 4 Apr 1997 22:00:22 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBMVK147K00B24A@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 4 Apr 1997 21:56:47 PST Date: Fri, 04 Apr 1997 21:56:46 -0800 (PST) From: schelvac@plu.edu Subject: Learning Group Problem #7 To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I had another question regarding the learning group. In the first problem, is the sodium ethoxide used up at all, or is it just become a modified product? I know that it reacts with the 2-chloro-2,3-dimethylbutane to create a new alkene, but what form does the rest of the sodium ethoxide take? Thanks, Alethea From davidsct@plu.edu Sat Apr 5 00:08:37 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id AAA11038 for ; Sat, 5 Apr 1997 00:08:36 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHBRCS638000AXL8@plu.edu> for organic1@rainier.chem.plu.edu; Sat, 5 Apr 1997 00:05:14 PST Date: Sat, 05 Apr 1997 00:05:12 -0800 (PST) From: davidsct@plu.edu Subject: Re: Forwarded mail.... In-reply-to: To: nicholrc@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I am not exactly forsure how the carbon-halogen bond breaks, but I do know that the timing of the bond depends on whether or not the reaction is an Sn1, Sn2, or E1, or E2. Once that is determined you can use the information discussed in lecture today to go from there. hope this helps a little bit, if any at all. cd On Fri, 4 Apr 1997 nicholrc@plu.edu wrote: > > > ---------- Forwarded message ---------- > Date: Wed, 19 Mar 1997 14:51:36 -0800 (PST) > From: nicholrc@plu.edu > To: organic@rainier.chem.plu.edu > Cc: nicholrc@plu.edu > > When and how does a carbon-halogen bond break? > > > nicholrc@plu.edu > > > From hartkg@plu.edu Sat Apr 5 16:16:17 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA15931 for ; Sat, 5 Apr 1997 16:16:15 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHCP5J198G009X3M@plu.edu> for organic1@rainier.chem.plu.edu; Sat, 5 Apr 1997 16:12:53 PST Date: Sat, 05 Apr 1997 16:12:52 -0800 (PST) From: hartkg@plu.edu Subject: dehydrohalogenations To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII ??? When completing dehydrohalogenations of alkyl halide reactions what is the best way to determine which proton will be removed from the halide by a strong base? Kristen From sounthna@plu.edu Sat Apr 5 16:51:55 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA16177 for ; Sat, 5 Apr 1997 16:51:54 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHCQELUD0G00A7I4@plu.edu> for organic1@rainier.chem.plu.edu; Sat, 5 Apr 1997 16:48:28 PST Date: Sat, 05 Apr 1997 16:48:26 -0800 (PST) From: sounthna@plu.edu Subject: Re: Sn2 vs E2 In-reply-to: To: super freak Cc: boothcj@plu.edu, davidsct@plu.edu, kamperka@plu.edu, greenjn@plu.edu, organic1, ~joelm@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The MSDS has been on line for a while now. You can use ether-net or pepper. Just go to the department of chemistry homepage and scroll down...you find it. N.s On Fri, 4 Apr 1997, super freak wrote: > does anyone know if the msds's are online yet? anyone know when they plan > to be? thanks! > > lj > > ~~~~ > joelm@plu.edu > > ~~~~ > 'KISS ME BABY, I'M VACINATED!' --another crazy chic > > > From stensetj@plu.edu Sat Apr 5 19:53:00 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id TAA17092 for ; Sat, 5 Apr 1997 19:52:58 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHCWPWI5WW00A7K8@plu.edu> for organic1@rainier.chem.plu.edu; Sat, 5 Apr 1997 19:49:23 PST Date: Sat, 05 Apr 1997 19:49:21 -0800 (PST) From: stensetj@plu.edu Subject: Re: Sn2,Sn1 rxn In-reply-to: To: holsinal@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII In an sn1 reaction there are two steps in the first "step" the alkyl halide is removed and it becomes a carbocation and then it is attacked by the nucleophile. It becomes a racemic mixture in the case when a stereocenter is formed on the carbocation. In a sn2 reaction these steps happen simultaneously during the transition, the nucleophile joins as the alkyl halide leaves. On Mon, 31 Mar 1997 holsinal@plu.edu wrote: > Can anyone help me with the basic differences between the transition > states of the sn1 and sn2 reactions, thanks. > > From stensetj@plu.edu Sat Apr 5 20:49:30 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA17446 for ; Sat, 5 Apr 1997 20:49:28 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHCYP4Z57C00A7K8@plu.edu> for organic1@rainier.chem.plu.edu; Sat, 5 Apr 1997 20:46:01 PST Date: Sat, 05 Apr 1997 20:45:59 -0800 (PST) From: stensetj@plu.edu Subject: Re: antbonding In-reply-to: To: peeblere@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII in antibonding, the orbitals bonded have opposite phase signs which overlap, in bonding, the orbitals bonded have the same phase sign and they combine together, an antibonding orbital has higher energy than a bonding orbital. On Fri, 4 Apr 1997 peeblere@plu.edu wrote: > Could someone explan the dfference between antibonding and normal > bondng? The tutors were not quite sure how to explain it wthout confusng > me more. > > From hoffmasb@plu.edu Sun Apr 6 08:24:55 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id IAA21043 for ; Sun, 6 Apr 1997 08:24:55 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHDKW2HSGW00ALRX@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 6 Apr 1997 07:21:30 PST Date: Sun, 06 Apr 1997 07:21:30 -0800 (PST) From: hoffmasb@plu.edu Subject: lab To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I don't exaclty understand exercise number two in the lab about the mechanism. Is it like the material we went over in lecture on Friday? hoffmasb From steelecl@plu.edu Sun Apr 6 13:40:01 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id NAA22838 for ; Sun, 6 Apr 1997 13:39:59 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHDXZ0V50G00BEPL@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 6 Apr 1997 13:36:31 PST Date: Sun, 06 Apr 1997 13:36:31 -0800 (PST) From: steelecl@plu.edu To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII On the Ch. 7 study sheet, it says that we should be able to understand the influence of carbocation stability on the ease of alcohol dehydration. I know that the more substituted cation is the more stable one, but I do not understand what effect this has on the alcohol dehydration. Could someone please explain this? Caroline From carlisel@plu.edu Sun Apr 6 23:11:36 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id XAA25588 for ; Sun, 6 Apr 1997 23:11:35 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHEHXMEREO00C23W@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 6 Apr 1997 23:08:04 PST Date: Sun, 06 Apr 1997 23:08:03 -0800 (PST) From: carlisel@plu.edu Subject: Re: Lab questions In-reply-to: To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Can someone help me with number 2 of the lab questions? Thanks From hiattzr@plu.edu Sun Apr 6 23:31:18 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id XAA25757 for ; Sun, 6 Apr 1997 23:31:17 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHEIMJ5IF400B2L3@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 6 Apr 1997 23:27:31 PST Date: Sun, 06 Apr 1997 23:27:24 -0800 (PST) From: hiattzr@plu.edu Subject: Re: dehydrohalogenations In-reply-to: To: hartkg@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Kristen, The proton that will be removed is the one that will lead to the more stable (or more highly substituted) alkene being formed. This is called Zaitsev's rule, its on page 304-305 of Solomons. There are exceptions to this rule when bulky bases are used, and steric hindrance prevents the bulky base from removing the proton that would lead to the more stable alkene. See page 305 section 7.12B for more detail. I hope this helps... Zach On Sat, 5 Apr 1997 hartkg@plu.edu wrote: > ??? > When completing dehydrohalogenations of alkyl halide reactions what is the > best way to determine which proton will be removed from the halide by a > strong base? > > Kristen > > From bobbtl@plu.edu Sun Apr 6 23:49:02 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id XAA25913 for ; Sun, 6 Apr 1997 23:49:00 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHEJ8VGO3K00B3W9@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 6 Apr 1997 23:45:27 PST Date: Sun, 06 Apr 1997 23:45:23 -0800 (PST) From: bobbtl@plu.edu Subject: Re: Forwarded mail.... In-reply-to: To: nicholrc@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII No, Na cannot act as a nucleophile because a nucleophile has to have at least one non-bonding pair of electron. Because Na has only one valence electron, it will tend to give that electron away and carry a positive negative charge. The nucleophile will then be the carbanion which received the electron from Na. On Fri, 4 Apr 1997 nicholrc@plu.edu wrote: > > > ---------- Forwarded message ---------- > Date: Wed, 19 Mar 1997 14:54:21 -0800 (PST) > From: nicholrc@plu.edu > To: organic@rainier.chem.plu.edu > Cc: nicholrc@plu.edu > > Can sodium (Na) act as a nucleophile? > > > nicholrc@plu.edu > > > From charbogd@plu.edu Mon Apr 7 00:27:29 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id AAA26558 for ; Mon, 7 Apr 1997 00:27:27 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHEKLTOORK00BFKD@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 7 Apr 1997 00:24:02 PST Date: Mon, 07 Apr 1997 00:24:02 -0800 (PST) From: "Gabriel D. Charbonneau" Subject: Lab 13 IR Spectra To: Organic Chemlist Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Chason and I were wondering what the peak at approx. 1100 cm-1 represents. We haven't been able to find a reference for this range anywhere in Solomons or Pavia :( gabe From kamperka@plu.edu Mon Apr 7 09:59:58 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id JAA29793 for ; Mon, 7 Apr 1997 09:59:57 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHF4LMM2S000C4UR@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 7 Apr 1997 09:56:34 PST Date: Mon, 07 Apr 1997 09:56:33 -0800 (PST) From: kamperka@plu.edu Subject: Re: Sn2 vs E2 In-reply-to: To: davidsct@plu.edu Cc: greenjn@plu.edu, organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII When he refers to a bulky base, it is often a tertiary one. An example is in the learning group problem for chapter seven; where potassium tert-butoxide is (KOC(CH3)3) the bulky base. On Fri, 4 Apr 1997 davidsct@plu.edu wrote: > A couple of questions about the answer below What did Freyle mean by a > bulky base, what is the defenition so to speak of a bulky base? ANd when > -COK is written down does that stand for an Alkoxide? > > cd > > On Fri, 4 Apr 1997 kamperka@plu.edu wrote: > > > > > It seems to me that the products will be a combination of the two types. > > Which will be the majority will depend on the nature of the > > base/nucleophile used. He gave an example in class today where the base > > was (CH3)3COK, a bulky base, and the major product was by the E1 reaction > > and the minor one was by the SN2 reaction. This is because bulky bases > > react mostly by E1 mechanisms, but can react by SN2 in the minority. > > > > Hope this makes sense > > -KK > > > > On Thu, 3 Apr 1997 greenjn@plu.edu wrote: > > > > > Even though this is something I should probably know by now, when Sn2 and > > > E2 reactions compete, is the product entirely one or the other? Or is it > > > a higher concentration of one and a lower concentration of another? > > > > > > > > > > > > From joelm@plu.edu Mon Apr 7 14:36:11 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id OAA01559 for ; Mon, 7 Apr 1997 14:36:11 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHFE94OZBK00AOQM@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 7 Apr 1997 14:32:49 PDT Date: Mon, 07 Apr 1997 14:32:48 -0700 (PDT) From: super freak Subject: Re: lab In-reply-to: To: hoffmasb@plu.edu Cc: organic1, ~joelm@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII for my answer i wrote an a mechanism of how my alcohol would react. there is an example in solomon's in ch 7. it's just about the same. i just showed the steps...ya, kinda like friday. hope this helps. =) lj On Sun, 6 Apr 1997 hoffmasb@plu.edu wrote: > I don't exaclty understand exercise number two in the lab about the > mechanism. Is it like the material we went over in lecture on Friday? > hoffmasb > > ~~~~ joelm@plu.edu ~~~~ 'KISS ME BABY, I'M VACINATED!' --another crazy chic From joelm@plu.edu Mon Apr 7 14:46:31 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id OAA01696 for ; Mon, 7 Apr 1997 14:46:30 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHFELT8S0W00BLX0@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 7 Apr 1997 14:43:03 PDT Date: Mon, 07 Apr 1997 14:43:01 -0700 (PDT) From: super freak Subject: Re: Lab 13 IR Spectra In-reply-to: To: "Gabriel D. Charbonneau" Cc: Organic Chemlist , ~joelm@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII i think the spike at 1100 is in the 'fingerprint' part of the spectrum. i found no reference to it either and i accounted for all the other types of bonds in the compound. lj On Mon, 7 Apr 1997, Gabriel D. Charbonneau wrote: > Chason and I were wondering what the peak at approx. 1100 cm-1 represents. > We haven't been able to find a reference for this range anywhere in > Solomons or Pavia :( > > gabe > > > ~~~~ joelm@plu.edu ~~~~ 'KISS ME BABY, I'M VACINATED!' --another crazy chic From fryhle@u.washington.edu Mon Apr 7 17:37:33 1997 Received: from jason02.u.washington.edu (jason02.u.washington.edu [140.142.76.8]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id RAA02699 for ; Mon, 7 Apr 1997 17:37:32 -0700 Received: from homer31.u.washington.edu (homer31.u.washington.edu [140.142.78.17]) by jason02.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id RAA13844 for ; Mon, 7 Apr 1997 17:34:12 -0700 Received: from localhost (fryhle@localhost) by homer31.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id RAA87524 for ; Mon, 7 Apr 1997 17:34:12 -0700 Date: Mon, 7 Apr 1997 17:34:11 -0700 (PDT) From: Craig Fryhle To: Organic Chemistry I List Subject: Midterm Info Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings, all. Later this week I will remove the answer key for our first exam from the display case by the Open Lab. I'll then put up a copy of an old exam that covers material which will be on next week's exam. Also, today I posted a spreadhsheet with Learning Group scores and quiz grades through chapter 6. The sheet also shows a midterm total and percentage, counting only the first exam and the six quizzes. I will send out midterm advisory notices to those folks with percentages less than 65 for the exam and quiz total (the first six). According to what I stated in the syllabus, grades from C- to C+ will fall in the range of 55-71 percent. If you'd like to discuss your progress, feel free to stopy by or arrange a meeting time. Now is a good time to focus or re-direct some effort if your current class standing is not what you would like it to be. All for now, CBF ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From fryhle@u.washington.edu Mon Apr 7 18:03:23 1997 Received: from jason02.u.washington.edu (jason02.u.washington.edu [140.142.76.8]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id SAA02889 for ; Mon, 7 Apr 1997 18:03:22 -0700 Received: from homer31.u.washington.edu (homer31.u.washington.edu [140.142.78.17]) by jason02.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id SAA14140 for ; Mon, 7 Apr 1997 18:00:02 -0700 Received: from localhost (fryhle@localhost) by homer31.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id SAA75062 for ; Mon, 7 Apr 1997 18:00:02 -0700 Date: Mon, 7 Apr 1997 18:00:02 -0700 (PDT) From: Craig Fryhle To: Organic Chemistry I List Subject: Class Time/Learning Group Activities Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings, again, folks. I'd like to add a few comments about class activities pertaining to Learning Groups. I am generally quite pleased by the solutions to Learning Group problems that groups have brought to class on their potential presentation days. I can see that good effort has been made by those preparing to present their work. Where I have concern, though, is with regard to participation and attendance by those not scheduled for a given day. The problems I write for the Learning Groups are designed to bring up key points from organic chemistry. The problems highlight and serve to present essential topics. Hence, it is strongly advised that everyone spend some time trying to learn from the problems that are provided for the Learning Groups. Each person, perhaps with their group, should spend some time working the Learning Group problems before the day scheduled for that problem, even if their group is not scheduled to present. Expecting this, I make enough copies of each problem for all members of the class. An additional aspect of concern is the level of attendance on Learning Group presentation days. If, as one of those not scheduled to present, you have not engaged a given Learning Group problem during your studies, it is understandable that class time during the presentations might not be as fulfilling as it could be for you. This reiterates the need for everyone to spend some time with all of the Learning Group problems. As I mentioned, I use the Learning Group presentations as vehicles for presentating key concepts in organic chemistry. Also, as I stated in the syllabus, material related to Learning Group problems will appear on exams. So, please help yourself learn more, by working on the Learning Group problems for days when your group is not scheduled to present and by attending class regularly (no matter what type of class activity is scheduled). Keep up the hard work! I can see that a lot of learning is taking place. I'd just like to see that more happens and that it happens more evenly. Ciao for now, CBF ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From hartkg@plu.edu Mon Apr 7 19:29:07 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id TAA03324 for ; Mon, 7 Apr 1997 19:29:05 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHFOH9M6C000CKVD@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 7 Apr 1997 19:25:42 PDT Date: Mon, 07 Apr 1997 19:25:42 -0700 (PDT) From: hartkg@plu.edu Subject: Problem 7.19 To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Why is there no reaction for problems 7.19a and 7.19b? Kristen From baileyle@plu.edu Mon Apr 7 20:46:01 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA03762 for ; Mon, 7 Apr 1997 20:45:59 -0700 Received: from Hind215b.PLU.EDU by plu.edu (PMDF V5.1-5 #17589) with SMTP id <01IHFR4NKQ2K00C0EU@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 7 Apr 1997 20:41:49 PDT Date: Mon, 07 Apr 1997 20:40:17 -0700 From: Lora Bailey Subject: group 2 To: organic1 Reply-to: baileyle@plu.edu Message-id: <3349BE21.7FBE@plu.edu> MIME-version: 1.0 X-Mailer: Mozilla 3.01 (Win95; I) Content-type: text/plain; charset=us-ascii Content-transfer-encoding: 7bit Hey, we've got the next learning group problem. When do you want to get together? If we want any help, we have to do it before Friday. Let me know, Lora From harriscr@plu.edu Tue Apr 8 00:29:03 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id AAA05462 for ; Tue, 8 Apr 1997 00:29:02 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHFYY1438I00BOT1@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 8 Apr 1997 00:25:33 PDT Date: Tue, 08 Apr 1997 00:25:32 -0700 (PDT) From: harriscr@plu.edu Subject: rings To: Organic chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Hi How do you figure out how many rings a structure will have be just looking at it's formula. (ie. C15C24) From harriscr@plu.edu Tue Apr 8 00:31:02 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id AAA05525 for ; Tue, 8 Apr 1997 00:31:01 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHFZ0MXQO800BOT1@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 8 Apr 1997 00:27:38 PDT Date: Tue, 08 Apr 1997 00:27:38 -0700 (PDT) From: harriscr@plu.edu Subject: anti-,syn-, perpilanar To: Organic chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Hi Do anti and syn periplanar positions only occur in the transition state in E2 reactions. Thanks, Clayton From youngcf@plu.edu Tue Apr 8 16:33:04 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA13590 for ; Tue, 8 Apr 1997 16:33:03 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHGWM9VK1S00CKFE@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 8 Apr 1997 16:29:36 PDT Date: Tue, 08 Apr 1997 16:29:35 -0700 (PDT) From: youngcf@plu.edu Subject: Re: Lab 13 In-reply-to: To: Harvey the Wonder Hamster Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The purpose is for the sodium bicarbonate to react with any HCl left in the solution. Youngcf@plu.edu. On Fri, 4 Apr 1997, Harvey the Wonder Hamster wrote: > > What WAS the purpose, as outlined in question 1, of washing the > crude t-pentyl chloride with sodium bicarbonate? > > From hendrycl@plu.edu Tue Apr 8 21:43:31 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA15452 for ; Tue, 8 Apr 1997 21:43:30 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHH7FR0NA800CR4X@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 8 Apr 1997 21:39:43 PDT Date: Tue, 08 Apr 1997 21:39:42 -0700 (PDT) From: hendrycl@plu.edu Subject: lab 13 To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Page 155 of last weeks lab reads, "A small amount of alkene, 2-methyl-2-butene, is produced as a by-product in this reaction. If sulfuric acid had been used as it was for n-butyl bromide, a much larger amount of this alkene would have been produced." Gabe and I assumed the 2-methyl-2-butene was formed through an E2 dehydration reaction in which a base (nucleophile) grabs a hydrogen from the reactant in order to produce the alkene. Wouldn't sulfuric acid form a weaker conjugate base than hydrochloric acid? So wouldn't the base formed from the disassociation of sulfuric acid be a poorer nucleophile and produce less alkene than the base formed from the disassociation of HCl? chase From hiattzr@plu.edu Wed Apr 9 00:42:12 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id AAA16635 for ; Wed, 9 Apr 1997 00:42:11 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHHDOS1PFK00C4RS@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 9 Apr 1997 00:38:46 PDT Date: Wed, 09 Apr 1997 00:38:45 -0700 (PDT) From: hiattzr@plu.edu Subject: Re: Problem 7.19 In-reply-to: To: hartkg@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Kristen, There is no reaction for 7.19a because and acid/base reaction between the given molecules would lead to the formation of the stronger acid and the stronger base, (see page 320 for the acid/base strengths of the molecules given). Earlier in the class (Chap. 3), we learned that acid/base reactions do not go in this direction. In 17.9b there is a reaction, the stonger base NH2 takes a proton off of the stronger acid, (the terminal alkyne) to form the weaker acid, ammonia, and the weaker base, the alkynide ion. The relative acidities and basicities of all of these molecules are again given on page 320. I hope this helps. Zachary On Mon, 7 Apr 1997 hartkg@plu.edu wrote: > > Why is there no reaction for problems 7.19a and 7.19b? > > Kristen > > From malonekn@plu.edu Wed Apr 9 14:32:28 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id OAA20870 for ; Wed, 9 Apr 1997 14:32:27 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHI6OROCC000COG0@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 9 Apr 1997 14:28:47 PDT Date: Wed, 09 Apr 1997 14:28:44 -0700 (PDT) From: malonekn@plu.edu Subject: Re: your mail In-reply-to: To: stensesk@plu.edu Cc: thomasbs@plu.edu, organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Just a small modification on the definition provided by Sacha--a meso compound is a specific type of achiral compound, which has tetrahedral stereocenters. a molecule like HO-CH2-Br is achiral, but is NOT a meso compound, because it has no stereocenter. the cyclic compound from the Chapter 7 quiz, on the other hand, IS a meso compound. On Sat, 29 Mar 1997 stensesk@plu.edu wrote: > If it is a meso compound it is achiral meaning it can be superposable on > its mirror image. I hope this helps you. > > Sasha > > On Thu, 27 Mar 1997 thomasbs@plu.edu wrote: > > > What determines if a compound is a meso compound? Any help would be > > appreciated. > > > > > > From malonekn@plu.edu Wed Apr 9 14:44:19 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id OAA20949 for ; Wed, 9 Apr 1997 14:44:18 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHI73J4WEI00COG0@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 9 Apr 1997 14:40:46 PDT Date: Wed, 09 Apr 1997 14:40:40 -0700 (PDT) From: malonekn@plu.edu Subject: Re: Meso Compound In-reply-to: To: cancel Cc: schliema@plu.edu, Organic Journal club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I just wanted to point out that in this case, the molecule is ONLY considered a meso compound if it is achiral. There is no such thing as a chiral meso compound. Sorry to be redundant, but I got this wrong on the Chapter 7 quiz, so I'd like to rescue everyone else from making the same mistake.-km On Wed, 2 Apr 1997, cancel wrote: > Mark- > I think that 2,3-Dibromobutane itself, as an alkane, is considered a meso > compound. Whether or not it is achiral depends on how it is drawn. In > other words, it is superposable on it's mirror image depending on how the > atoms are arranged around the stereocenter. So therefore, it's not just > one enantiomer which is considered a meso compound, but the whole alkane > itself, because of the way the atoms can be arranged. > -Kate > > On Mon, 31 Mar 1997 schliema@plu.edu wrote: > > > On page 207, when the book describes what a Meso compound is, I'm not sure > > I quite understand what the Meso compound is. What I mean is, are all 3 > > of the molecules of 2,3-Dibromobutane called Meso compounds or is it just > > the one molecule that is seperate from the other two in the book? The > > book wasn't quite clear on this. So if anybody could help, please clarify > > this for me. > > > > Thanks, > > Mark > > > > > > > > From malonekn@plu.edu Wed Apr 9 14:47:52 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id OAA21054 for ; Wed, 9 Apr 1997 14:47:51 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHI7896CDU00COG0@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 9 Apr 1997 14:44:26 PDT Date: Wed, 09 Apr 1997 14:44:26 -0700 (PDT) From: malonekn@plu.edu In-reply-to: To: organic1 Cc: Organic Journal Club Reply-to: malonekn@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I just wanted to second this motion.--km On Wed, 2 Apr 1997, Sourcrout wrote: > This request is really for Dr. Fryhle, but I should post it anyway. > I wanted to inquire on behalf of a small handful of other students about > the possibility of a study-guide regarding what reactions we should > memorize for the exam. There is a plethera of methods and reactions > throughout chapter 6 and 7 and Dr. Fryhle noted in today's lecture that we > didn't need to know the method for a select couple. Although I would love > to take the time to memorize all the reactions, I would prefer to fill my > limited-capacity cortex with needed information if possible. Is this a > reasonable request to ask what we need to know for the test? > > MC > > From malonekn@plu.edu Wed Apr 9 14:49:38 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id OAA21114 for ; Wed, 9 Apr 1997 14:49:37 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHI7AAD7GA00COG0@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 9 Apr 1997 14:46:05 PDT Date: Wed, 09 Apr 1997 14:46:04 -0700 (PDT) From: malonekn@plu.edu Subject: Re: general question In-reply-to: To: maschhjt@plu.edu Cc: organic1 , bekemj@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Hello. I was just wondering if anyone knew an easy way to remember the E-Z thing. With all this stuff we have to memorize, any snazzy tricks would be extremely helpful.-km From schwarkl@plu.edu Wed Apr 9 14:56:05 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id OAA21218 for ; Wed, 9 Apr 1997 14:56:04 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHI7HZGQAE009N2W@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 9 Apr 1997 14:52:24 PDT Date: Wed, 09 Apr 1997 14:52:18 -0700 (PDT) From: Katy Schwartz Subject: Re: general question In-reply-to: To: malonekn@plu.edu Cc: Organic Chemlist Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Kath--My high school chem teacher was full of cheesy memorization tricks, but I think they really work. For E-Z, he always said: E="Epposite" side, and Z="Zame" side I don't know if this will help at all, but it works for me.--Katy On Wed, 9 Apr 1997 malonekn@plu.edu wrote: > Hello. I was just wondering if anyone knew an easy way to remember the > E-Z thing. With all this stuff we have to memorize, any snazzy tricks > would be extremely helpful.-km > > From fryhle@u.washington.edu Wed Apr 9 17:09:36 1997 Received: from jason01.u.washington.edu ([140.142.70.24]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id RAA22024 for ; Wed, 9 Apr 1997 17:09:36 -0700 Received: from homer33.u.washington.edu (homer33.u.washington.edu [140.142.76.15]) by jason01.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id RAA14150 for ; Wed, 9 Apr 1997 17:06:13 -0700 Received: from localhost (fryhle@localhost) by homer33.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id RAA102116 for ; Wed, 9 Apr 1997 17:06:13 -0700 Date: Wed, 9 Apr 1997 17:06:13 -0700 (PDT) From: Craig Fryhle To: Organic Journal Club Subject: Reaction Review In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings, folks. In reply to the posting below, I'd suggest that you now take a look at the handout I gave you at the beginning of the class entitled "Summary of Reactions by Type". This handout organizes reactions into classes (substitution, elimination, addition, etc) and also provides a summary entitled "Methods for Functional Group Preparation". The information is keyed to the section of the text where further information can be found. As you will see, there are some reactions we have not come to yet, but since you can tell which chapter each reaction comes from you can focus your efforts on the chapters we have covered to date. However, I would not advise using the summary sheet as a means to learn the reactions. Rather, it is designed to help you organize them in your mind and jog your memory once you have already learned them. In addition, I would suggest looking at the summaries given at the end of each chapter on the reactions covered therein. Again, use these for review, not the initial learning. About providing a laundry list of reactions to learn. As you probably realize now, it would be impossible to write a list of all the SN2 reactions that are possible. Or SN1, or E1 or E2 reactions, for that matter. The world is full of nucleophiles, bases, and compounds with leaving groups. What is necessary is for you to realize what combinations of reagents in general will bring about each class of reaction. For example, do you have a good leaving group, is the nucleophile simultaneously a strong base or not, does the substrate have a sterically hindered leaving group, or is it easily accessed by a nucleophile, ...? So, know what the characteristics are of a good nucleophile, of a good base, when one a reagent can act in either capacity, how the structure of the substrate influences the reaction pathway. Also note typical conditions for various reactions (solvent, temperature, etc). Know the stereochemical outcome of each type of reaction. Be able to reproduce from memory the transition states and key intermediates for SN2, SN1, E2 and E1 reactions. As to addition reactions, know the general characteristics of how an alkene can behave as a nucleophile. Be able to recognize which parts of reagents can act as electrophiles and be attacked by an alkene, and what the remaining reagent part is that then acts as a nucleophile. Use the summaries of reactions in Chapter 8 for addition reactions to alkenes and alkynes. Try to recognize the common mechanistic themes among them and use this to help you remember. Finally, use the Study Sheets that I gave you as a packet at the beginning of the semester to know what you should "come away" with after studying each section in the text. If we come upon specific and unique reactions that you do not need to know or whose mechanism you do not need to know, I'll tell you. One, for example, is the dissolving metal reduction of alkynes to E alkenes using Li/EtNH2, etc. You should be able to use these conditions to make an E alkene from an alkyne, but since this mechanism is unique to itself, I do not expect you to memorize it. There will be a couple of others like this in Chapter 8 (the oxidation reactions at the end - you need to be able to use them, but the mechanisms do not need to be known in detail). Work the problems and truly challenge yourself before seeking the answer from the Study Guide or someone else. There is no other way to learn chemistry without doing problems. Try to identify the concepts that a given problem is trying to help you learn. Well, I hope these things are of help to you. Keep up the hard work. CBF > On Wed, 2 Apr 1997, Sourcrout wrote: > > > This request is really for Dr. Fryhle, but I should post it anyway. > > I wanted to inquire on behalf of a small handful of other students about > > the possibility of a study-guide regarding what reactions we should > > memorize for the exam. There is a plethera of methods and reactions > > throughout chapter 6 and 7 and Dr. Fryhle noted in today's lecture that we > > didn't need to know the method for a select couple. Although I would love > > to take the time to memorize all the reactions, I would prefer to fill my > > limited-capacity cortex with needed information if possible. Is this a > > reasonable request to ask what we need to know for the test? > > > > MC > > > > > > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From baileyle@plu.edu Wed Apr 9 17:23:15 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id RAA22164 for ; Wed, 9 Apr 1997 17:23:15 -0700 Received: from Hind215b.PLU.EDU by plu.edu (PMDF V5.1-5 #17589) with SMTP id <01IHICNWUM0I00C3PY@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 9 Apr 1997 17:19:50 PDT Date: Wed, 09 Apr 1997 17:18:19 -0700 From: Lora Bailey Subject: group2 To: organic1 Reply-to: baileyle@plu.edu Message-id: <334C31CB.108C@plu.edu> MIME-version: 1.0 X-Mailer: Mozilla 3.01 (Win95; I) Content-type: text/plain; charset=us-ascii Content-transfer-encoding: 7bit About learning group problem 8; I talked with Cliff, and he said that he could meet tomorrow night, so how about 8:00pm? Let me know. From rorabajh@plu.edu Thu Apr 10 00:27:02 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id AAA09111 for ; Thu, 10 Apr 1997 00:27:01 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHIRG9TVKW00CSBT@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 10 Apr 1997 00:23:34 PDT Date: Thu, 10 Apr 1997 00:23:33 -0700 (PDT) From: rorabajh@plu.edu Subject: Re: group2 In-reply-to: <334C31CB.108C@plu.edu> To: Lora Bailey Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII thursday night around eight will probably be ok with me -jen On Wed, 9 Apr 1997, Lora Bailey wrote: > About learning group problem 8; I talked with Cliff, and he said that he > could meet tomorrow night, so how about 8:00pm? Let me know. > From wongew@plu.edu Thu Apr 10 13:04:42 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id NAA13324 for ; Thu, 10 Apr 1997 13:04:41 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHJHVZTGUO00E0G7@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 10 Apr 1997 13:00:44 PDT Date: Thu, 10 Apr 1997 13:00:42 -0700 (PDT) From: wongew@plu.edu Subject: Re: group2 In-reply-to: To: rorabajh@plu.edu Cc: Lora Bailey , organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII 8pm is fine with me too. From frickeje@plu.edu Thu Apr 10 20:05:01 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA15694 for ; Thu, 10 Apr 1997 20:05:00 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHJWLOYGBK00EJ7Y@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 10 Apr 1997 20:01:31 PDT Date: Thu, 10 Apr 1997 20:01:31 -0700 (PDT) From: frickeje@plu.edu Subject: Learning Group Presentation # 8 To: Organic Chemistry List Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Does anyone know whether Ch. 8 learning group presentation is on Friday or Monday? I have gotten both answers from everyone I already asked, but no one knows for sure. -JF From baileyle@plu.edu Thu Apr 10 20:38:27 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA15985 for ; Thu, 10 Apr 1997 20:38:27 -0700 Received: from Hind215b.PLU.EDU by plu.edu (PMDF V5.1-5 #17589) with SMTP id <01IHJXR3MJNE00DU82@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 10 Apr 1997 20:34:53 PDT Date: Thu, 10 Apr 1997 20:33:22 -0700 From: Lora Bailey Subject: Re: Learning Group Presentation # 8 To: organic1, frickeje@plu.edu Reply-to: baileyle@plu.edu Message-id: <334DB102.1C8D@plu.edu> MIME-version: 1.0 X-Mailer: Mozilla 3.01 (Win95; I) Content-type: text/plain; charset=us-ascii Content-transfer-encoding: 7bit References: It's on Monday I think. He spent an extra day on chpt 7, so the learning group presentations are on Monday instead of the review for the test. Please tell me if I'm wrong because my group may have to present. From fryhle@u.washington.edu Thu Apr 10 22:44:20 1997 Received: from jason03.u.washington.edu (jason03.u.washington.edu [140.142.77.10]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA16690 for ; Thu, 10 Apr 1997 22:44:19 -0700 Received: from homer16.u.washington.edu (homer16.u.washington.edu [140.142.70.17]) by jason03.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id WAA19758; Thu, 10 Apr 1997 22:40:56 -0700 Received: from localhost (fryhle@localhost) by homer16.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id WAA16288; Thu, 10 Apr 1997 22:40:56 -0700 Date: Thu, 10 Apr 1997 22:40:55 -0700 (PDT) From: Craig Fryhle To: frickeje@plu.edu cc: Organic Chemistry List Subject: Re: Learning Group Presentation # 8 In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings, all. Last week when I adjusted the course calendar to allow three days for chapter 7 I announced that each of the days for chapter 8 would be pushed back one day (the review day is eliminated). Thus, the chapter 8 LGP will be on Monday. The exam is on Wednesday, as scheduled. I will offer a group problem session during office hours on Monday (12:30-2) so that whatever topics are requested for review can taken up. CBF On Thu, 10 Apr 1997 frickeje@plu.edu wrote: > Does anyone know whether Ch. 8 learning group presentation is on > Friday or Monday? I have gotten both answers from everyone I already > asked, but no one knows for sure. > > -JF > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From craigtm@plu.edu Fri Apr 11 07:50:42 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id HAA19643 for ; Fri, 11 Apr 1997 07:50:42 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHKL8RD3O0000G0X@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 11 Apr 1997 07:47:17 PDT Date: Fri, 11 Apr 1997 07:47:17 -0700 (PDT) From: craigtm@plu.edu Subject: lab 15 To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII COULD SOMEONE GIVE ME AN IDEA ABOUT EXERCISE 1 FOR EXPERIMENT 15??? From kamperka@plu.edu Fri Apr 11 09:44:43 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id JAA20299 for ; Fri, 11 Apr 1997 09:44:42 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHKP811SZ400E10Y@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 11 Apr 1997 09:41:15 PDT Date: Fri, 11 Apr 1997 09:41:13 -0700 (PDT) From: kamperka@plu.edu Subject: Re: Learning Group Presentation # 8 In-reply-to: To: frickeje@plu.edu Cc: Organic Chemistry List Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Its on Monday On Thu, 10 Apr 1997 frickeje@plu.edu wrote: > Does anyone know whether Ch. 8 learning group presentation is on > Friday or Monday? I have gotten both answers from everyone I already > asked, but no one knows for sure. > > -JF > > From fryhle@u.washington.edu Fri Apr 11 12:54:49 1997 Received: from jason04.u.washington.edu (jason04.u.washington.edu [140.142.78.5]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id MAA21414 for ; Fri, 11 Apr 1997 12:54:48 -0700 Received: from homer26.u.washington.edu (homer26.u.washington.edu [140.142.78.16]) by jason04.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id MAA18232 for ; Fri, 11 Apr 1997 12:51:24 -0700 Received: from localhost (fryhle@localhost) by homer26.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id MAA91582 for ; Fri, 11 Apr 1997 12:51:24 -0700 Date: Fri, 11 Apr 1997 12:51:23 -0700 (PDT) From: Craig Fryhle To: Organic Chemistry I List Subject: Formal Lab Reports Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings, folks. The week after next is the week scheduled for preparation of the Group Formal Lab Report. Begin to discuss with your group what your top two or three choices would be for experiments on which to write your collaborative formal report. By mid-week I'll ask you to mark your group's number next to your top three experiment choices on a posted list of experiments. I'll give as many groups their first or second choice as possible. Also next week, I'll indicate any personnel changes between groups that might be necessary in order to have the group formal reports work (these changes would only be for the writing of the lab report). CBF ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From joelm@plu.edu Fri Apr 11 14:51:25 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id OAA22623 for ; Fri, 11 Apr 1997 14:51:24 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHKZX7VT2O00FB8U@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 11 Apr 1997 14:47:53 PDT Date: Fri, 11 Apr 1997 14:47:52 -0700 (PDT) From: super freak Subject: Re: Formal Lab Reports In-reply-to: To: Craig Fryhle Cc: Organic Chemistry I List , ~joelm@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII where is the list of topics for formal lab? what if our chosen topic is not on the list? do we even get to have a list of potential topics? do we get to help in creating this list? anyone with more info, plz pass it on to me. thanks! lj ~~~~ joelm@plu.edu ~~~~ 'KISS ME BABY, I'M VACINATED!' --another crazy chic From fryhle@u.washington.edu Fri Apr 11 18:10:28 1997 Received: from jason05.u.washington.edu (jason05.u.washington.edu [140.142.78.6]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id SAA23872 for ; Fri, 11 Apr 1997 18:10:27 -0700 Received: from homer14.u.washington.edu (homer14.u.washington.edu [140.142.70.15]) by jason05.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id SAA22098; Fri, 11 Apr 1997 18:07:02 -0700 Received: from localhost (fryhle@localhost) by homer14.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id SAA39950; Fri, 11 Apr 1997 18:07:02 -0700 Date: Fri, 11 Apr 1997 18:07:02 -0700 (PDT) From: Craig Fryhle To: super freak cc: Organic Chemistry I List , ~joelm@plu.edu Subject: Re: Formal Lab Reports In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Laura, the list of topics is simply the list of experiment titles. Groups will write formal lab reports about one of the experiments they have conducted so far. The lab syllabus has more information about formal lab reports. CBF On Fri, 11 Apr 1997, super freak wrote: > where is the list of topics for formal lab? what if our chosen topic is > not on the list? do we even get to have a list of potential topics? do we > get to help in creating this list? anyone with more info, plz pass it on > to me. thanks! > > lj > > ~~~~ > joelm@plu.edu > > ~~~~ > 'KISS ME BABY, I'M VACINATED!' --another crazy chic > > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From balaislv@plu.edu Fri Apr 11 19:42:50 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id TAA24411 for ; Fri, 11 Apr 1997 19:42:49 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHLA4M8IS20001QA@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 11 Apr 1997 19:39:23 PDT Date: Fri, 11 Apr 1997 19:39:23 -0700 (PDT) From: "L.B." Subject: Re: Learning Group Presentation # 8 In-reply-to: To: frickeje@plu.edu Cc: Organic Chemistry List Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Jen, it will be on Monday because the exam's on Wednesday. Good Luck on it (and to everyone else). Lani *~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~* ~ Leilani Ria Vieglo Balais ~ * ~~~~~~~~~~~~~~~~~~~~~~~~~ * ~ ~ * Pacific Lutheran University * ~ E-mail Address: balaislv@plu.edu ~ * (206) 535-7718 * ~ ~ *~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~* On Thu, 10 Apr 1997 frickeje@plu.edu wrote: > Does anyone know whether Ch. 8 learning group presentation is on > Friday or Monday? I have gotten both answers from everyone I already > asked, but no one knows for sure. > > -JF > > From rorabajh@plu.edu Sat Apr 12 13:56:53 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id NAA11227 for ; Sat, 12 Apr 1997 13:56:53 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHMCC1EWS00009B7@plu.edu> for organic1@rainier.chem.plu.edu; Sat, 12 Apr 1997 13:53:25 PDT Date: Sat, 12 Apr 1997 13:53:25 -0700 (PDT) From: rorabajh@plu.edu Subject: ch.7 questions To: The Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII i'm about to write up a bunch of questions i have about the ch. 7 problems, so if anyone has any info/help for any of them, please write back: for 7.6c, i don't understand how to determine how the number of rings can be determined in a molecule (in general, not just the problem given) i know someone sorta asked this earlier, but no one has answered yet. thanks, jen From rorabajh@plu.edu Sat Apr 12 14:02:59 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id OAA11334 for ; Sat, 12 Apr 1997 14:02:59 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHMCJMDJHY0009B7@plu.edu> for organic1@rainier.chem.plu.edu; Sat, 12 Apr 1997 13:59:32 PDT Date: Sat, 12 Apr 1997 13:59:32 -0700 (PDT) From: rorabajh@plu.edu Subject: 7.25b To: The Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII in 7.25b, i don't understand how isopropyl chloride was changed into a propene; specifically, i don't know why the answer uses those specific reagents (CH3CH2ONa & CH3CH2OH) -jen From archerka@plu.edu Sat Apr 12 14:09:34 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id OAA11405 for ; Sat, 12 Apr 1997 14:09:34 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHMCRSD3Y8000ACC@plu.edu> for organic1@rainier.chem.plu.edu; Sat, 12 Apr 1997 14:06:07 PDT Date: Sat, 12 Apr 1997 14:06:07 -0700 (PDT) From: archerka@plu.edu Subject: Chem lab To: organic chemistry list Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII For our chemistry lab questions does anyone know what major alkene product is produced from 1,2-Cyclohexanediol? (#2,e) What is keto-enol tautomerism? Thanks -Kristy From rorabajh@plu.edu Sat Apr 12 14:10:04 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id OAA11434 for ; Sat, 12 Apr 1997 14:10:03 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHMCSC0T640009B7@plu.edu> for organic1@rainier.chem.plu.edu; Sat, 12 Apr 1997 14:06:33 PDT Date: Sat, 12 Apr 1997 14:06:33 -0700 (PDT) From: rorabajh@plu.edu Subject: 7.35d To: The Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII why is CH3 l CH3-C-CH2-CH=CH2 l CH3 the major product over CH3 l CH3-C-CH=CH-CH3 ? l CH3 I Thought the more substituted alkene was the major product. does it have to do with the hindrance of the leaving hydrogen? -jen From rorabajh@plu.edu Sat Apr 12 14:19:04 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id OAA11543 for ; Sat, 12 Apr 1997 14:19:04 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHMD3KJJNM0009B7@plu.edu> for organic1@rainier.chem.plu.edu; Sat, 12 Apr 1997 14:15:37 PDT Date: Sat, 12 Apr 1997 14:15:37 -0700 (PDT) From: rorabajh@plu.edu Subject: 7.36a To: The Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII in 36, we're supposed to use the appropriate alkyl halide and base; i was wondering why i was supposed to use H H l l H-C-C-CH2CH2CH3 l l H Br instead of H H l l H-C-C-CH2CH2CH3 l l Br H and, i was also wondering why i should use (CH3)3COK and (CH3)COH instead of the C2H5ONa and C2H5OH as they used in the examples earlier in the chapter-- is a bulky base preferred in this case, or did they just decide to throw something different in there? why? -jen From rorabajh@plu.edu Sat Apr 12 14:22:09 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id OAA11620 for ; Sat, 12 Apr 1997 14:22:09 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHMD7EHAP40009B7@plu.edu> for organic1@rainier.chem.plu.edu; Sat, 12 Apr 1997 14:18:42 PDT Date: Sat, 12 Apr 1997 14:18:42 -0700 (PDT) From: rorabajh@plu.edu Subject: 7.43 and 7.46 To: The Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII these two questions sort of fall back on that ring question- how do we know when there are rings? the book really doesn't offer a clear answer, or a basic formula to follow. help! -jen From carlisel@plu.edu Sat Apr 12 15:33:11 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA12058 for ; Sat, 12 Apr 1997 15:33:10 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHMFOCX6ZK000A42@plu.edu> for organic1@rainier.chem.plu.edu; Sat, 12 Apr 1997 15:29:40 PDT Date: Sat, 12 Apr 1997 15:29:39 -0700 (PDT) From: carlisel@plu.edu Subject: Determining numbers of rings in a molecule In-reply-to: To: rorabajh@plu.edu Cc: The Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII When determining the munber of rings, one must first find the index of hydrogen deficiency for the molecule in question, Zingiberene, in this case. The formula of the alkene is C15H32, the formula for Zingiberene is C15H24. The difference is H8 (H32-H24=H8), which equals 4 pairs of hydrogen atoms. So the index of Hydrogen Deficiency is 4. OK, now that we know that, we figure out all the structual possibilities that are in place of the 4 pairs of hydrogen atoms. A double bond takes up one pair, a triple bond takes up two pairs, and a ring takes up one pair of Hydrogen atoms: Structural Possibilites: 4 rings 4 double bonds 3 double bonds, 1 rings 2 double bonds, 2 ring 3 rings, 1 double bond 2 triple bonds etc. We were told in the problem that there are no triple bonds, and we found in part (b) that there are 3 double bonds. That would mean that the only possiblity would be : 3 double bonds and 1 ring. So when determining the number of rings, find the Index of Hydrogen Deficiency and play around with the different structural possibilities to see which one works. I hope this helps. On Sat, 12 Apr 1997 rorabajh@plu.edu wrote: > > for 7.6c, i don't understand how to determine how the number of rings can > be determined in a molecule (in general, not just the problem given) > i know someone sorta asked this earlier, but no one has answered yet. > > thanks, > > jen > > > From rorabajh@plu.edu Sat Apr 12 17:37:29 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id RAA12725 for ; Sat, 12 Apr 1997 17:37:29 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHMK1JPUWW000B9G@plu.edu> for organic1@rainier.chem.plu.edu; Sat, 12 Apr 1997 17:34:02 PDT Date: Sat, 12 Apr 1997 17:34:02 -0700 (PDT) From: rorabajh@plu.edu Subject: ch. 5 question To: The Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII looking back on the questions of ch. 5, i don't understand something in #35-- why the structures in part h are enantiomers, and the structures in part i are the same. i'd draw them out here, but they are chair conformations, they are on p.221 in solomons. -jen From fickesje@plu.edu Sat Apr 12 19:33:37 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id TAA13372 for ; Sat, 12 Apr 1997 19:33:36 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHMO3GHGDS000CJJ@plu.edu> for organic1@rainier.chem.plu.edu; Sat, 12 Apr 1997 19:30:07 PDT Date: Sat, 12 Apr 1997 19:30:06 -0700 (PDT) From: fickesje@plu.edu Subject: Re: 7.35d In-reply-to: To: rorabajh@plu.edu Cc: The Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The reason why 4,4-dimethylpent-1-ene is the major product is because of hofmann's rule. With the large tert-butyl group at the end there is a great amount of steric bulk. This makes it difficult to remove a H from the 3rd carbon, which is a secondary carbon. So the nucleophile seeks out a hydrogen which is more exposed, in this case it takes one from the first carbon. It talks about this on page 305. I hope this helps. jen On Sat, 12 Apr 1997 rorabajh@plu.edu wrote: > > > > why is > > CH3 > l > CH3-C-CH2-CH=CH2 > l > CH3 > > the major product over > > CH3 > l > CH3-C-CH=CH-CH3 ? > l > CH3 > > > I Thought the more substituted alkene was the major product. does it have > to do with the hindrance of the leaving hydrogen? > > -jen > > From bowersmy@plu.edu Sat Apr 12 20:57:36 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA13831 for ; Sat, 12 Apr 1997 20:57:35 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHMR0O2GMO000CPG@plu.edu> for organic1@rainier.chem.plu.edu; Sat, 12 Apr 1997 20:54:08 PDT Date: Sat, 12 Apr 1997 20:54:08 -0700 (PDT) From: bowersmy@plu.edu Subject: hydrogen deficiency To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I pretty much understand hydrogen deficiency, i think, but i was wondering what the hydrogen deficiency would be for a cycloalkene. From steelecl@plu.edu Sun Apr 13 16:33:19 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA19676 for ; Sun, 13 Apr 1997 16:33:19 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHNW3BNWHC000OEX@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 13 Apr 1997 16:29:51 PDT Date: Sun, 13 Apr 1997 16:29:51 -0700 (PDT) From: steelecl@plu.edu To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Can someone explain stereospecific reactions. Is that what Dr. Fryhle was talking about when he said something could attack from either side, but in it actually only attacks from one side? Caroline From sounthna@plu.edu Sun Apr 13 20:28:14 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA20856 for ; Sun, 13 Apr 1997 20:28:13 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHO4AJGTDC000NSE@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 13 Apr 1997 20:24:45 PDT Date: Sun, 13 Apr 1997 20:24:45 -0700 (PDT) From: sounthna@plu.edu To: Questions!!! Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Hey class...can someone explain free energy to me. I was reviewing the stability of carbocations and did not know what they meant or what free energy meant in the overall reaction. Thanks Ns. From mistkaam@plu.edu Sun Apr 13 21:21:06 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA21178 for ; Sun, 13 Apr 1997 21:21:05 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHO64YNHSC000T38@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 13 Apr 1997 21:17:31 PDT Date: Sun, 13 Apr 1997 21:17:30 -0700 (PDT) From: mistkaam@plu.edu Subject: Re: Formal Lab Reports In-reply-to: To: super freak Cc: Craig Fryhle , Organic Chemistry I List , ~joelm@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I believe that you have to do the formal report on one of labs which we have done. On Fri, 11 Apr 1997, super freak wrote: > where is the list of topics for formal lab? what if our chosen topic is > not on the list? do we even get to have a list of potential topics? do we > get to help in creating this list? anyone with more info, plz pass it on > to me. thanks! > > lj > > ~~~~ > joelm@plu.edu > > ~~~~ > 'KISS ME BABY, I'M VACINATED!' --another crazy chic > > > From hoffmasb@plu.edu Sun Apr 13 22:09:53 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA21500 for ; Sun, 13 Apr 1997 22:09:53 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHO7TLKWBK000TVO@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 13 Apr 1997 22:06:23 PDT Date: Sun, 13 Apr 1997 22:06:23 -0700 (PDT) From: hoffmasb@plu.edu Subject: double dehydrogenation To: organic chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Was that a double dehydrogenation Dr. Fryhle wass talking about that would cause the formation of an alkyne? In an experiment, how would one be able to tell that all of the solution had formed a triple bond? Sara From hoffmasb@plu.edu Sun Apr 13 22:11:19 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA21531 for ; Sun, 13 Apr 1997 22:11:19 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHO7V7YKVA000TVO@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 13 Apr 1997 22:07:42 PDT Date: Sun, 13 Apr 1997 22:07:42 -0700 (PDT) From: hoffmasb@plu.edu Subject: lab To: organic chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII In last weeks lab, what werre the results supposed to be for the saturation test? I am not sure if mine worked out quite right. Sara From carlisel@plu.edu Sun Apr 13 22:25:48 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA21675 for ; Sun, 13 Apr 1997 22:25:47 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHO8E6UL40000WH2@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 13 Apr 1997 22:22:14 PDT Date: Sun, 13 Apr 1997 22:22:13 -0700 (PDT) From: carlisel@plu.edu Subject: Re: lab In-reply-to: To: hoffmasb@plu.edu Cc: organic chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII If you look in the lab book on page 169 it discusses the results. Compounds with double bonds (4-methlycyclohexene) turn colorless when they react with bromine solution, and turn brown when they react with potassium permanganate. Any other reaction would show that double bonds were not present. On Sun, 13 Apr 1997 hoffmasb@plu.edu wrote: > In last weeks lab, what werre the results supposed to be for the > saturation test? I am not sure if mine worked out quite right. > Sara > > From baileyle@plu.edu Sun Apr 13 22:48:01 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA21860 for ; Sun, 13 Apr 1997 22:48:01 -0700 Received: from Hind215b.PLU.EDU by plu.edu (PMDF V5.1-5 #17589) with SMTP id <01IHO95THJ1C000USM@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 13 Apr 1997 22:44:30 PDT Date: Sun, 13 Apr 1997 22:43:00 -0700 From: Lora Bailey Subject: Re: 7.35d To: rorabajh@plu.edu Cc: organic1 Reply-to: baileyle@plu.edu Message-id: <3351C3E3.4254@plu.edu> MIME-version: 1.0 X-Mailer: Mozilla 3.01 (Win95; I) Content-type: text/plain; charset=us-ascii Content-transfer-encoding: 7bit References: rorabajh@plu.edu wrote: > > why is > > CH3 > l > CH3-C-CH2-CH=CH2 > l > CH3 > > the major product over > > CH3 > l > CH3-C-CH=CH-CH3 ? > l > CH3 > > I Thought the more substituted alkene was the major product. does it have > to do with the hindrance of the leaving hydrogen? > > -jen It's because the reaction takes place in potassium tert-butoxide in tert-buytl alcohol. It's the exception to Zaitsev's rule. It's on page 305 , 7.12 B. From guestrp@plu.edu Mon Apr 14 07:54:45 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id HAA24917 for ; Mon, 14 Apr 1997 07:54:44 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHOS9O3M80000XFB@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 14 Apr 1997 07:51:14 PDT Date: Mon, 14 Apr 1997 07:51:13 -0700 (PDT) From: guestrp@plu.edu Subject: Re: hydrogen deficiency In-reply-to: To: bowersmy@plu.edu Cc: organic1 Reply-to: guestrp@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The hydrogen deficiency of a cycloalkene would be two. A cycloalkane is lacking two hydrogens, giving it a hydrogen deficiency of one. A alkene is also missing one pair of hydrogens, giving it a deficiency of one. When the two are added together you get a total hydrogen deficiency of two. On Sat, 12 Apr 1997 bowersmy@plu.edu wrote: > I pretty much understand hydrogen deficiency, i think, but i was wondering > what the hydrogen deficiency would be for a cycloalkene. > > From hartkg@plu.edu Mon Apr 14 16:27:27 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA27725 for ; Mon, 14 Apr 1997 16:27:23 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHPA4XGE7K0018YD@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 14 Apr 1997 16:22:52 PDT Date: Mon, 14 Apr 1997 16:22:49 -0700 (PDT) From: hartkg@plu.edu Subject: Re: your mail In-reply-to: To: steelecl@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Stereospecific reactions include a specific stereoisomeric reactant that will always form a particular stereoisomeric product. For example trans-2-butene will always form a meso compound. The study sheet states that from section 8.7 we should learn to determine the products of halogen addition to E and Z alkenes. If a halogen is added to a cis alkene the product will be chiral, and if a halogen is added to a trans alkene the product will be a meso compound. Kristen On Sun, 13 Apr 1997 steelecl@plu.edu wrote: > Can someone explain stereospecific reactions. Is that what Dr. Fryhle > was talking about when he said something could attack from either side, > but in it actually only attacks from one side? > Caroline > > From mistkaam@plu.edu Mon Apr 14 16:57:05 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA27954 for ; Mon, 14 Apr 1997 16:57:04 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHPB6WIH5Y0017R0@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 14 Apr 1997 16:53:27 PDT Date: Mon, 14 Apr 1997 16:53:25 -0700 (PDT) From: mistkaam@plu.edu Subject: Re: lab In-reply-to: To: hoffmasb@plu.edu Cc: organic chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII You were testing to see if your product contained alocohol or not. It should have taken more drops in your product than in the alcohol, because you didn't want alcohol in your product. I don't know if this answers what you were asking, but I hope it helps. On Sun, 13 Apr 1997 hoffmasb@plu.edu wrote: > In last weeks lab, what werre the results supposed to be for the > saturation test? I am not sure if mine worked out quite right. > Sara > > From barnetca@plu.edu Mon Apr 14 20:40:23 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA29211 for ; Mon, 14 Apr 1997 20:40:23 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHPIZQBYHS001D8N@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 14 Apr 1997 20:36:45 PDT Date: Mon, 14 Apr 1997 20:36:43 -0700 (PDT) From: barnetca@plu.edu Subject: Re: your mail In-reply-to: To: sounthna@plu.edu Cc: Questions!!! Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII For a clearer understanding of free energy, look at figure 6.2 on page 234 and read the paragraph below. I hope that helps! On Sun, 13 Apr 1997 sounthna@plu.edu wrote: > Hey class...can someone explain free energy to me. I was > reviewing the stability of carbocations and did not know what they meant > or what free energy meant in the overall reaction. Thanks > > Ns. > > From 107744.2473@compuserve.com Mon Apr 14 21:59:22 1997 Received: from hil-img-2.compuserve.com (hil-img-2.compuserve.com [149.174.177.132]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA29654 for ; Mon, 14 Apr 1997 21:59:21 -0700 Received: by hil-img-2.compuserve.com (8.6.10/5.950515) id AAA15239; Tue, 15 Apr 1997 00:55:52 -0400 Date: Tue, 15 Apr 1997 00:55:15 -0400 From: "howard r. kletke" <107744.2473@compuserve.com> Subject: lab To: unknown Message-ID: <199704150054_MC2-1448-B734@compuserve.com> In order to understand the reactions of cis-5,6-Norbornene-endo-2,3-dicarboxylic Anhydride, which mechanisms should be utilized? _Monica From fryhle@u.washington.edu Mon Apr 14 22:11:59 1997 Received: from jason03.u.washington.edu (jason03.u.washington.edu [140.142.77.10]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA29783 for ; Mon, 14 Apr 1997 22:11:59 -0700 Received: from homer05.u.washington.edu (homer05.u.washington.edu [140.142.76.12]) by jason03.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id WAA10342; Mon, 14 Apr 1997 22:08:30 -0700 Received: from localhost (fryhle@localhost) by homer05.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id WAA32856; Mon, 14 Apr 1997 22:08:30 -0700 Date: Mon, 14 Apr 1997 22:08:29 -0700 (PDT) From: Craig Fryhle To: rorabajh@plu.edu cc: The Organic Journal Club Subject: Determining Numbers of Rings In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Hi, all. There has already been one very good answer to the question of how to use index of hydrogen of deficiency (IHD) to determine the number of rings, but I'll add my $0.02. As stated in the other reply, one calculates what the IHD would be based on the molecular formula given. Then, one adds all the hydrogen pairs that can be added via hydrogenation reactions. After this, the IHD is calculated again based on the new molecular formula. The remaining IHD is due to rings (or carbonyl groups if there was oxygen in the formula), since the hydrogen deficiency of any alkynes and alkenes would have been reduced to the alkane stage, assuming H2 and platinum were used. If you wanted to test for alkynes only, one could use H2 and Lindlar's catalyst to reduce the initial compound, then check the IHD. The remaining deficiency would be due to alkenes, rings, and carbonyl groups, and the change in IHD from the start to after the Lindlar's catalyst reduction would correspond to alkyne groups. Note that when calculating IHD hydroxyl groups and halogen atoms are counted just like hydrogen in the forumla, since each takes the place of exactly one hydrogen. A carbonyl group, however, introduces one unit of hydrogen deficiency, since the carbonyl occupies a place where two hydrogens could have been. I hope that helps further re IHD, rings, etc. CBF ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From fryhle@u.washington.edu Mon Apr 14 22:18:41 1997 Received: from jason01.u.washington.edu (jason01.u.washington.edu [140.142.70.24]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA29890 for ; Mon, 14 Apr 1997 22:18:40 -0700 Received: from homer05.u.washington.edu (homer05.u.washington.edu [140.142.76.12]) by jason01.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id WAA11396; Mon, 14 Apr 1997 22:15:11 -0700 Received: from localhost (fryhle@localhost) by homer05.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id WAA48132; Mon, 14 Apr 1997 22:15:11 -0700 Date: Mon, 14 Apr 1997 22:15:11 -0700 (PDT) From: Craig Fryhle To: rorabajh@plu.edu cc: The Organic Journal Club Subject: E2 elimination reaction: problem 7.25b In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings. The conditions cited in the question below for the conversion of isopropyl chloride (2-chloropropane) to propene are classic conditions for an E2 reaction. CH3CH2ONa (sodium ethoxide) is an excellent base for dehydrohalogenations. CH3CH2OH (ethanol) is the solvent. The mechanism involves sodium ethoxide removing one of the hydrogens beta to the chlorine atom in isopropyl chloride. As this hydrogen is removed, the pair of electrons that used to bond it to the carbon is given to the area between the carbon where the hydrogen is being removed and the carbon bearing chlorine. The electron pair filling in to form the double bond adds a pair of electrons to the count for the carbon bearing the chlorine, requiring that something leave from that carbon in order to maintain an octet of electrons. Hence, the chlorine serves as a leaving group by departing with a pair of electrons. Section 7.12 in the text also depicts the mechanism. CBF On Sat, 12 Apr 1997 rorabajh@plu.edu wrote: > > in 7.25b, i don't understand how isopropyl chloride was changed into a > propene; specifically, i don't know why the answer uses those specific > reagents (CH3CH2ONa & CH3CH2OH) > > > -jen > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From fryhle@u.washington.edu Mon Apr 14 22:23:42 1997 Received: from jason01.u.washington.edu (jason01.u.washington.edu [140.142.70.24]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA29974 for ; Mon, 14 Apr 1997 22:23:42 -0700 Received: from homer05.u.washington.edu (homer05.u.washington.edu [140.142.76.12]) by jason01.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id WAA16956; Mon, 14 Apr 1997 22:20:13 -0700 Received: from localhost (fryhle@localhost) by homer05.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id WAA23334; Mon, 14 Apr 1997 22:20:13 -0700 Date: Mon, 14 Apr 1997 22:20:12 -0700 (PDT) From: Craig Fryhle To: archerka@plu.edu cc: organic chemistry list Subject: Re: Chem lab In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Howdy. I realize that you have all turned your labs in by now, but here is a word about this question. First, have a look at what you find about keto-enol tautomerism by looking in the index of the lecture text. Then, consider the dehydration of 1,2-cyclohexanediol in such a way that the double bond forms between the carbons where both hydroxyl groups originally were. After the dehydration to lose one hydroxyl group and a hydrogen to form the alkene, the remaining structural group is called an enol. It is an alkene-alcohol, hence the name enol. Enols isomerize to carbonyl groups in the way described in the text. I hope that helps to finish the puzzle. CBF On Sat, 12 Apr 1997 archerka@plu.edu wrote: > For our chemistry lab questions does anyone know what major alkene > product is produced from 1,2-Cyclohexanediol? (#2,e) What is keto-enol > tautomerism? > Thanks -Kristy > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From fryhle@u.washington.edu Mon Apr 14 22:26:29 1997 Received: from jason01.u.washington.edu (jason01.u.washington.edu [140.142.70.24]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA00065 for ; Mon, 14 Apr 1997 22:26:28 -0700 Received: from homer05.u.washington.edu (homer05.u.washington.edu [140.142.76.12]) by jason01.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id WAA10814; Mon, 14 Apr 1997 22:23:00 -0700 Received: from localhost (fryhle@localhost) by homer05.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id WAA58504; Mon, 14 Apr 1997 22:22:59 -0700 Date: Mon, 14 Apr 1997 22:22:59 -0700 (PDT) From: Craig Fryhle To: rorabajh@plu.edu cc: The Organic Journal Club Subject: Re: 7.35d In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Yes, the product below results because a sterically hindered base was used (potassium tert-butoxide). Hence, the most accessible beta hydrogen was removed, leading to the Hofmann product (less substituted alkene), rather than the Zaytzev product. CBF On Sat, 12 Apr 1997 rorabajh@plu.edu wrote: > > > > why is > > CH3 > l > CH3-C-CH2-CH=CH2 > l > CH3 > > the major product over > > CH3 > l > CH3-C-CH=CH-CH3 ? > l > CH3 > > > I Thought the more substituted alkene was the major product. does it have > to do with the hindrance of the leaving hydrogen? > > -jen > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From fryhle@u.washington.edu Mon Apr 14 22:48:24 1997 Received: from jason02.u.washington.edu (jason02.u.washington.edu [140.142.76.8]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA00288 for ; Mon, 14 Apr 1997 22:48:23 -0700 Received: from homer05.u.washington.edu (homer05.u.washington.edu [140.142.76.12]) by jason02.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id WAA13382 for ; Mon, 14 Apr 1997 22:44:55 -0700 Received: from localhost (fryhle@localhost) by homer05.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id WAA94646 for ; Mon, 14 Apr 1997 22:44:54 -0700 Date: Mon, 14 Apr 1997 22:44:54 -0700 (PDT) From: Craig Fryhle To: Organic Chemistry I List Subject: Stereoisomerism in alkene additions In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Hi, folks. Let me add a few caveats to this reply. On Mon, 14 Apr 1997 hartkg@plu.edu wrote: > Stereospecific reactions include a specific stereoisomeric reactant that > will always form a particular stereoisomeric product. For example > trans-2-butene will always form a meso compound. Yes, IF what is added adds the same thing to each end of the double bond and in an anti fashion. I would not consider the above a general rule, however. You need to evaluate each situation independently based on whether the alkene has the same things bonded at each end, whether it is E or Z, whether the adding reagent addes the same thing to each end, and whether it does so in a syn or anti fashion. >The study sheet states > that from section 8.7 we should learn to determine the products of halogen > addition to E and Z alkenes. >If a halogen is added to a cis alkene the > product will be chiral, and if a halogen is added to a trans alkene the > product will be a meso compound. > According to the factors I noted above, the previous statement is true IF the alkene has the same groups bonded at each end of the double bond (as is the case inE and Z 2-butene, but not, for example, in 2-pentene (E or Z). Cheerio, CBF > On Sun, 13 Apr 1997 steelecl@plu.edu wrote: > > > Can someone explain stereospecific reactions. Is that what Dr. Fryhle > > was talking about when he said something could attack from either side, > > but in it actually only attacks from one side? > > Caroline > > > > > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From fryhle@u.washington.edu Mon Apr 14 22:53:33 1997 Received: from jason01.u.washington.edu (jason01.u.washington.edu [140.142.70.24]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA00372 for ; Mon, 14 Apr 1997 22:53:32 -0700 Received: from homer05.u.washington.edu (homer05.u.washington.edu [140.142.76.12]) by jason01.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id WAA13780 for ; Mon, 14 Apr 1997 22:50:04 -0700 Received: from localhost (fryhle@localhost) by homer05.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id WAA44230 for ; Mon, 14 Apr 1997 22:50:03 -0700 Date: Mon, 14 Apr 1997 22:50:03 -0700 (PDT) From: Craig Fryhle To: organic chemistry Subject: Unsaturation tests In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings. Just a word about the tests for unsaturation. They were tests for the presence of the alkene product. The Br2 reagent and KMnO4 reagent react with alkenes to have the color of the original reagent discharged (disappear). Thus, if the product did not contain any alkene the color of the Br2 or the KMnO4 reagents would remain when added to the non-alkene sample. The tests do not show, however, that all of the alcohol was absent. Even if some alcohol were there, so long as there was predominently alkene present during the test the colors would be discharged. CBF On Mon, 14 Apr 1997 mistkaam@plu.edu wrote: > You were testing to see if your product contained alocohol or not. It > should have taken more drops in your product than in the alcohol, because > you didn't want alcohol in your product. I don't know if this answers > what you were asking, but I hope it helps. > > On Sun, 13 Apr 1997 hoffmasb@plu.edu wrote: > > > In last weeks lab, what werre the results supposed to be for the > > saturation test? I am not sure if mine worked out quite right. > > Sara > > > > > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From charbogd@plu.edu Mon Apr 14 22:56:00 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA00462 for ; Mon, 14 Apr 1997 22:56:00 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHPNPYKNDS001FPP@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 14 Apr 1997 22:52:24 PDT Date: Mon, 14 Apr 1997 22:52:24 -0700 (PDT) From: "Gabriel D. Charbonneau" Subject: Problem 6.17 To: Organic Chemlist Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII In problem 6.17 we are asked to synthesize several different products. I would like to know why in part (c) H20 is used as well as methyl alcohol for a solvent. In the previous questions it was not used. gabe From carlisel@plu.edu Mon Apr 14 23:23:36 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id XAA00692 for ; Mon, 14 Apr 1997 23:23:35 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHPOP3HAKG001IFP@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 14 Apr 1997 23:19:56 PDT Date: Mon, 14 Apr 1997 23:19:56 -0700 (PDT) From: carlisel@plu.edu Subject: TOJC Postings To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII It is required that we each do 10 email postings in the semester, 5 in the first half and 5 in the second half. Does anyone know in regards to this when the first half of the semester ended and the second half began? I would normally think it would be Spring Break, but he extended the date, but I am not sure by how much. From mistkaam@plu.edu Tue Apr 15 09:47:03 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id JAA04203 for ; Tue, 15 Apr 1997 09:47:02 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHQAH68EYE001PG7@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 15 Apr 1997 09:43:29 PDT Date: Tue, 15 Apr 1997 09:43:28 -0700 (PDT) From: mistkaam@plu.edu Subject: Re: TOJC Postings In-reply-to: To: carlisel@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII He extended the break to Saturday April 5! On Mon, 14 Apr 1997 carlisel@plu.edu wrote: > > It is required that we each do 10 email postings in the semester, > 5 in the first half and 5 in the second half. Does anyone know in regards > to this when the first half of the semester ended and the second half > began? I would normally think it would be Spring Break, but he extended > the date, but I am not sure by how much. > > From fryhle@u.washington.edu Tue Apr 15 11:02:11 1997 Received: from jason03.u.washington.edu (jason03.u.washington.edu [140.142.77.10]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id LAA04644 for ; Tue, 15 Apr 1997 11:02:08 -0700 Received: from homer03.u.washington.edu (homer03.u.washington.edu [140.142.70.13]) by jason03.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id KAA22428; Tue, 15 Apr 1997 10:58:39 -0700 Received: from localhost (fryhle@localhost) by homer03.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id KAA37414; Tue, 15 Apr 1997 10:58:39 -0700 Date: Tue, 15 Apr 1997 10:58:38 -0700 (PDT) From: Craig Fryhle To: "Gabriel D. Charbonneau" cc: Organic Chemlist Subject: Re: Problem 6.17 In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Gabe, water is necessary to dissolve the hydroxide reactant (presumably sodium hydroxide or potassium hydroxide). Neither is very soluble in methanol itself, so water is added as a co-solvent. Reactions must have the reagents in solution in order for them to make contact with each other. CBF On Mon, 14 Apr 1997, Gabriel D. Charbonneau wrote: > In problem 6.17 we are asked to synthesize several different products. I > would like to know why in part (c) H20 is used as well as methyl alcohol > for a solvent. In the previous questions it was not used. > > gabe > > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From fickesje@plu.edu Tue Apr 15 12:07:05 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id MAA05057 for ; Tue, 15 Apr 1997 12:07:04 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHQFCQ8Q9C001Q3E@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 15 Apr 1997 12:03:28 PDT Date: Tue, 15 Apr 1997 12:03:27 -0700 (PDT) From: fickesje@plu.edu Subject: Chp. 5 To: Organic chem Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I am confussed as to how an R configuration can be both (+) and (-) and the same with S. I thought R was going to rotate only (+) and S only (-). Why can they do both. Can someone please explain this to me. thank you. jen From fickesje@plu.edu Tue Apr 15 12:09:51 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id MAA05115 for ; Tue, 15 Apr 1997 12:09:50 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHQFG90LUE001Q3E@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 15 Apr 1997 12:06:16 PDT Date: Tue, 15 Apr 1997 12:06:16 -0700 (PDT) From: fickesje@plu.edu Subject: Acids and Bases To: Organic chem Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I know this seems pretty basic but can someone please explain acids and bases. I don't understand how to tell wether they are strong or weak. jen From vogega@plu.edu Tue Apr 15 12:16:15 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id MAA05227 for ; Tue, 15 Apr 1997 12:16:14 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHQFO3WFYQ001SG0@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 15 Apr 1997 12:12:38 PDT Date: Tue, 15 Apr 1997 12:12:37 -0700 (PDT) From: vogega@plu.edu Subject: Re: Chp. 5 In-reply-to: To: organic1, fickesje@plu.edu Reply-to: vogega@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII jen- (+) and (-) have to do with the optical rotation of the compound. they do not have to do with the configuration of the molecule. (+) means that the optical rotation is clockwise, as does the R. The R and (+), however, do not coorespond to the same thing. there is an explanation of this in the text book on pages 193-98. on page 198 it also talks about how there is no coorelation between R and (+) or(-). i hope this helps you. gretchen On Tue, 15 Apr 1997 fickesje@plu.edu wrote: > I am confussed as to how an R configuration can be both (+) and (-) and > the same with S. I thought R was going to rotate only (+) and S only (-). > Why can they do both. Can someone please explain this to me. thank you. > jen > > > From barnetca@plu.edu Tue Apr 15 16:48:33 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA11718 for ; Tue, 15 Apr 1997 16:48:33 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHQP6OOX5C001YW7@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 15 Apr 1997 16:44:55 PDT Date: Tue, 15 Apr 1997 16:44:55 -0700 (PDT) From: barnetca@plu.edu Subject: Ch.5 Additional problems To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Can someone please explain the differentiation that needs to be made when determining whether two compared models are enantiomers or two molecules of the same compound. For example 5.35 (a,b,d,e,h,i,l,p,q) on page 221. From barnetca@plu.edu Tue Apr 15 16:52:52 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA11753 for ; Tue, 15 Apr 1997 16:52:50 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHQPB9GZCM001YW7@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 15 Apr 1997 16:48:41 PDT Date: Tue, 15 Apr 1997 16:48:39 -0700 (PDT) From: barnetca@plu.edu Subject: Book mistake! To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII For those who have the STUDY GUIDE AND SOLUTIONS MANUAL, on page 65, problem 5.2, is there a mistake for the answer to that problem? I don't see how the answer can be "b". Wouldn't it be "e"? From fryhle@u.washington.edu Tue Apr 15 17:22:26 1997 Received: from jason01.u.washington.edu (jason01.u.washington.edu [140.142.70.24]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id RAA12045 for ; Tue, 15 Apr 1997 17:22:26 -0700 Received: from homer20.u.washington.edu (homer20.u.washington.edu [140.142.76.4]) by jason01.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id RAA10894; Tue, 15 Apr 1997 17:18:56 -0700 Received: from localhost (fryhle@localhost) by homer20.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id RAA73868; Tue, 15 Apr 1997 17:18:55 -0700 Date: Tue, 15 Apr 1997 17:18:55 -0700 (PDT) From: Craig Fryhle To: barnetca@plu.edu cc: organic1 Subject: Re: Book mistake! In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Hi, folks. The Study Guide is correct. Structure (b) on page 65, problem 5.2 of the Study Guide possesses a plane of symmetry directly between the two fluorine atoms. The plane bisects the Cl, C and Br atoms. But, please do point out to me any errors that you may find in either the main text or the Study Guide. Check the list of errors I have posted on the bulletin board by the stockroom (or the email list I sent a month ago) to be sure the error you found has not already been noted. Any that you find I will see get corrected in future printings of the book. Thanks, CBF On Tue, 15 Apr 1997 barnetca@plu.edu wrote: > For those who have the STUDY GUIDE AND SOLUTIONS MANUAL, on page 65, > problem 5.2, is there a mistake for the answer to that problem? I don't > see how the answer can be "b". Wouldn't it be "e"? > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From balaislv@plu.edu Tue Apr 15 23:27:53 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id XAA14479 for ; Tue, 15 Apr 1997 23:27:52 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHR34UKC1C002ADG@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 15 Apr 1997 23:24:18 PDT Date: Tue, 15 Apr 1997 23:24:17 -0700 (PDT) From: "L.B." Subject: Re: TOJC Postings In-reply-to: To: carlisel@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII You were supposed to get in at least 5 postings by Friday, April 4. The following Monday was the start of the second half of the semester. Leilani *~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~* ~ Leilani Ria Vieglo Balais ~ * ~~~~~~~~~~~~~~~~~~~~~~~~~ * ~ ~ * Pacific Lutheran University * ~ E-mail Address: balaislv@plu.edu ~ * (206) 535-7718 * ~ ~ *~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~* On Mon, 14 Apr 1997 carlisel@plu.edu wrote: > > It is required that we each do 10 email postings in the semester, > 5 in the first half and 5 in the second half. Does anyone know in regards > to this when the first half of the semester ended and the second half > began? I would normally think it would be Spring Break, but he extended > the date, but I am not sure by how much. > > From erickstd@plu.edu Thu Apr 17 13:28:47 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id NAA27330 for ; Thu, 17 Apr 1997 13:28:46 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHTASPATPY0035UU@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 17 Apr 1997 13:25:11 PDT Date: Thu, 17 Apr 1997 13:25:10 -0700 (PDT) From: THE PENGUIN To: O-Chem List Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII hey y'all, how long does this weeks lab take? timmy XXXX X XXX/ XXXXXX\ XXXX XXXXX# X**XX### X***X##### X***X##### X**XX##### *XXXX### XXXXXX ^^^^^^^^^ Dooby Dooby Doo!! From vogega@plu.edu Thu Apr 17 15:06:56 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA28097 for ; Thu, 17 Apr 1997 15:06:55 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHTE89VU5S002XEC@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 17 Apr 1997 15:03:16 PDT Date: Thu, 17 Apr 1997 15:03:13 -0700 (PDT) From: vogega@plu.edu Subject: Re: your mail In-reply-to: To: organic1, THE PENGUIN Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII This weeks lab took me about an hour and a half to do the first part. You have to come back in the next day or so to finish the lab. Your crystals have to dry before you can melt them. Make sure that they have dried long enough. I know people that waited a day but the crystals weren't dry enough and there compound formed a sticky goo when they melted it. I haven't finished the second part, but I am assuming that it won't take long-less than an hour. Gretchen On Thu, 17 Apr 1997, THE PENGUIN wrote: > hey y'all, how long does this weeks lab take? > timmy > XXXX > X XXX/ > XXXXXX\ > XXXX > XXXXX# > X**XX### > X***X##### > X***X##### > X**XX##### > *XXXX### > XXXXXX > ^^^^^^^^^ > > Dooby Dooby Doo!! > > From vogega@plu.edu Thu Apr 17 15:08:19 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA28132 for ; Thu, 17 Apr 1997 15:08:18 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHTE9WYWFS002XEC@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 17 Apr 1997 15:04:32 PDT Date: Thu, 17 Apr 1997 15:04:31 -0700 (PDT) From: vogega@plu.edu Subject: group 19 To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII do any of you have a preference as to which lab we do for the formal lab write up? we need to go sign up for our three choices soon. let me know and i will go sign us up for the labs. gretchen From blackkl@plu.edu Thu Apr 17 15:22:58 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA28323 for ; Thu, 17 Apr 1997 15:22:57 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHTESBHQW0003BUE@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 17 Apr 1997 15:19:22 PDT Date: Thu, 17 Apr 1997 15:19:22 -0700 (PDT) From: blackkl@plu.edu Subject: Group 4.. To: Organic Chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Does anyone know which labs they would prefer to do for our formal lab write up? I know it really doesn't matter to me but he told us that we had to sign up by Friday morning so if any of you have a preference then sign up and then just let me know which one you chose..K? Thanks! Kristey From taylormr@plu.edu Thu Apr 17 16:20:28 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA28730 for ; Thu, 17 Apr 1997 16:20:27 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHTGSJJXES0030F5@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 17 Apr 1997 16:16:49 PDT Date: Thu, 17 Apr 1997 16:16:49 -0700 (PDT) From: "M.Taylor" Subject: this week's lab To: organic1 Reply-to: "M.Taylor" Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII On part two of this week's lab, when we have to heat the sample to approximately 130 degrees, do we have to heat it for a certain amount of time or due we just wait until it reaches 130 degrees before we begin to allow it to cool? michele From mistkaam@plu.edu Thu Apr 17 17:15:00 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id RAA29089 for ; Thu, 17 Apr 1997 17:14:59 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHTIP5T2LY0033DN@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 17 Apr 1997 17:11:21 PDT Date: Thu, 17 Apr 1997 17:11:20 -0700 (PDT) From: mistkaam@plu.edu Subject: Re: your mail In-reply-to: To: THE PENGUIN Cc: O-Chem List Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Not very long. The first part took me aobut an hour and the second part took about 45 min. On Thu, 17 Apr 1997, THE PENGUIN wrote: > hey y'all, how long does this weeks lab take? > timmy > XXXX > X XXX/ > XXXXXX\ > XXXX > XXXXX# > X**XX### > X***X##### > X***X##### > X**XX##### > *XXXX### > XXXXXX > ^^^^^^^^^ > > Dooby Dooby Doo!! > > From mistkaam@plu.edu Thu Apr 17 17:23:52 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id RAA29187 for ; Thu, 17 Apr 1997 17:23:51 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHTJ0704MC0033DN@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 17 Apr 1997 17:20:15 PDT Date: Thu, 17 Apr 1997 17:20:14 -0700 (PDT) From: mistkaam@plu.edu Subject: Re: this week's lab In-reply-to: To: "M.Taylor" Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Just wait until it heats up to about 130 degrees. On Thu, 17 Apr 1997, M.Taylor wrote: > > On part two of this week's lab, when we have to heat the sample to > approximately 130 degrees, do we have to heat it for a certain amount of > time or due we just wait until it reaches 130 degrees before we begin to > allow it to cool? > > michele > > > > > From smithtw@plu.edu Thu Apr 17 17:28:38 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id RAA29227 for ; Thu, 17 Apr 1997 17:28:37 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHTJ61J2L20039DF@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 17 Apr 1997 17:24:58 PDT Date: Thu, 17 Apr 1997 17:24:57 -0700 (PDT) From: smithtw@plu.edu Subject: Re: this week's lab In-reply-to: To: "M.Taylor" Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Michele Heat the sample until the crystals melt and you get a very clear and colorless liquid in your beaker. The melting happens very quicky, so once it melts you can take it off the heat and allow it to cool. Good Luck! Tobin On Thu, 17 Apr 1997, M.Taylor wrote: > > On part two of this week's lab, when we have to heat the sample to > approximately 130 degrees, do we have to heat it for a certain amount of > time or due we just wait until it reaches 130 degrees before we begin to > allow it to cool? > > michele > > > > > From maschhjt@plu.edu Thu Apr 17 17:28:59 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id RAA29252 for ; Thu, 17 Apr 1997 17:28:59 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHTJ6LNTSM002T9R@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 17 Apr 1997 17:25:25 PDT Date: Thu, 17 Apr 1997 17:25:24 -0700 (PDT) From: maschhjt@plu.edu Subject: Re: this week's lab In-reply-to: To: organic1 , "M.Taylor" Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Michele I just heated it to 130 degrees and then took it off and let it cool. As Gretchen said, i also got a wierd goo after i heated my bromohydrin. i dont know if this is exactly correct or not, but if someone does i would be very appreciative if they could tell me! I was also wondering if anyone knew what the melting points were supposed to be? i cant remember what mine were off hand, but i was not able to find them anywhere, so if anyone could tell me what they got so we could compare that would be great! thanx bunches Justin On Thu, 17 Apr 1997, M.Taylor wrote: > > On part two of this week's lab, when we have to heat the sample to > approximately 130 degrees, do we have to heat it for a certain amount of > time or due we just wait until it reaches 130 degrees before we begin to > allow it to cool? > > michele > > > > > From fryhle@u.washington.edu Thu Apr 17 21:52:15 1997 Received: from jason02.u.washington.edu (jason02.u.washington.edu [140.142.76.8]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA00777 for ; Thu, 17 Apr 1997 21:52:15 -0700 Received: from homer35.u.washington.edu (homer35.u.washington.edu [140.142.78.18]) by jason02.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id VAA06684 for ; Thu, 17 Apr 1997 21:48:42 -0700 Received: from localhost (fryhle@localhost) by homer35.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id VAA153390 for ; Thu, 17 Apr 1997 21:48:42 -0700 Date: Thu, 17 Apr 1997 21:48:42 -0700 (PDT) From: Craig Fryhle To: Organic Chemistry I List Subject: Formal lab Report Group Assignments Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings, everyone. Here are some additional details regarding the formal lab reports, group sizes, and job descriptions. I. By my analysis, the following Learning Groups have only three members for the formal lab report: 1, 2, 6, 9, 10, 15, 16, 19, 20, 21, 22 Groups 14 and 18 will combine to make four people for the formal report. Group 11 will add two members whose names I will tell you in class on Friday. All other groups not mentioned above have four members. II. If your group has four members, proceed with the job descriptions for writing the report just as described in the lab syllabus. See numbers IV. and V. below, too. III. If your group has three members, here's how the work should be divided among three people: Introduction (20 points) First Individual Results, Discussion and Conclusion (20 points) Second Individual Experimental Section (20 points) Third Individual Title, Abstract, Registry Numbers, Notation and Format of References (20 points) Divided among the group so that the total workload is equitable. The final 20 points (to toal 100) will be made by adding an individual's score again to the total from above. The names and roles of group members are to be noted at the end of the report, with signatures from all members. IV. Read the lab syllabus about formal lab reports to be sure you have all the details down regarding the mechanics/format for preparing your report. And, make use of the sample paper provided as an ideal model for your finished report. V. As noted in the syllabus, expectations are high for the quality of writing and analysis in the formal lab reports. It is expected that a group will constructively evaluate each other's writing and work together to see that all the component sections meld into one coherent and well-organized report. It is expected that several drafts of each section and of the final paper will be reviewed by the group. All for now, CBF ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From muellesb@plu.edu Thu Apr 17 22:27:18 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA01038 for ; Thu, 17 Apr 1997 22:27:17 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHTTLCR6YO003DW5@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 17 Apr 1997 22:23:38 PDT Date: Thu, 17 Apr 1997 22:23:38 -0700 (PDT) From: Firefly Subject: lab handouts To: Organic Chemlist Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The stockroom was out of lab handouts today. This is the second time this has happened to me. Can something be done so they don't run out? From fryhle@u.washington.edu Fri Apr 18 07:16:15 1997 Received: from jason03.u.washington.edu (jason03.u.washington.edu [140.142.77.10]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id HAA04002 for ; Fri, 18 Apr 1997 07:16:14 -0700 Received: from homer07.u.washington.edu (homer07.u.washington.edu [140.142.77.11]) by jason03.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id HAA16482; Fri, 18 Apr 1997 07:12:41 -0700 Received: from localhost (fryhle@localhost) by homer07.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id HAA66058; Fri, 18 Apr 1997 07:12:41 -0700 Date: Fri, 18 Apr 1997 07:12:41 -0700 (PDT) From: Craig Fryhle To: Firefly cc: Organic Chemlist Subject: Re: lab handouts In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII I always prepare more copies than there are students in the class, not including the additional copies I always make for faculty and stockroom workers. Perhaps I should ask that people not take extra copies for friends in lab, scratch paper, or whatever. I am trying not to use more paper for this class than necessary, however I will continue to make a few extra copies of every handout. CBF On Thu, 17 Apr 1997, Firefly wrote: > The stockroom was out of lab handouts today. This is the second time this > has happened to me. Can something be done so they don't run out? > > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From craigtm@plu.edu Fri Apr 18 07:42:36 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id HAA04151 for ; Fri, 18 Apr 1997 07:42:36 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHUCZSNUQO003LWB@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 18 Apr 1997 07:38:56 PDT Date: Fri, 18 Apr 1997 07:38:55 -0700 (PDT) From: craigtm@plu.edu Subject: Re: your mail In-reply-to: To: THE PENGUIN Cc: O-Chem List Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII the first day it takes about 1 1\2 hours max and the second day takes about 45 minutes. On Thu, 17 Apr 1997, THE PENGUIN wrote: > hey y'all, how long does this weeks lab take? > timmy > XXXX > X XXX/ > XXXXXX\ > XXXX > XXXXX# > X**XX### > X***X##### > X***X##### > X**XX##### > *XXXX### > XXXXXX > ^^^^^^^^^ > > Dooby Dooby Doo!! > > From craigtm@plu.edu Fri Apr 18 07:45:12 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id HAA04206 for ; Fri, 18 Apr 1997 07:45:11 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHUD333QFC003LWB@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 18 Apr 1997 07:41:34 PDT Date: Fri, 18 Apr 1997 07:41:34 -0700 (PDT) From: craigtm@plu.edu Subject: Re: group 19 In-reply-to: To: vogega@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Gretchen, it really doesn't matter to me which lab we do. Maybe pick one of the first few that we did. You can go ahead and sign up for whatever one though. Tiffany On Thu, 17 Apr 1997 vogega@plu.edu wrote: > do any of you have a preference as to which lab we do for the formal lab > write up? we need to go sign up for our three choices soon. let me know > and i will go sign us up for the labs. > gretchen > > From craigtm@plu.edu Fri Apr 18 07:49:22 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id HAA04329 for ; Fri, 18 Apr 1997 07:49:21 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHUD8AQI6O003LWB@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 18 Apr 1997 07:45:46 PDT Date: Fri, 18 Apr 1997 07:45:46 -0700 (PDT) From: craigtm@plu.edu Subject: Re: this week's lab In-reply-to: To: maschhjt@plu.edu Cc: organic1 , "M.Taylor" Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Justin, I also got that wierd goo the first time I did it. I found that it helped to scrape the sides and the bottom with the glass stirring rod. My melting points were 100 and 115-120. I don't know if this is correct or not but that's what I got. Tiffany On Thu, 17 Apr 1997 maschhjt@plu.edu wrote: > > Michele > > I just heated it to 130 degrees and then took it off and let it cool. As > Gretchen said, i also got a wierd goo after i heated my bromohydrin. i > dont know if this is exactly correct or not, but if someone does i would > be very appreciative if they could tell me! I was also wondering if anyone > knew what the melting points were supposed to be? i cant remember what > mine were off hand, but i was not able to find them anywhere, so if anyone > could tell me what they got so we could compare that would be great! > > thanx bunches > Justin > > On Thu, 17 Apr 1997, M.Taylor wrote: > > > > > On part two of this week's lab, when we have to heat the sample to > > approximately 130 degrees, do we have to heat it for a certain amount of > > time or due we just wait until it reaches 130 degrees before we begin to > > allow it to cool? > > > > michele > > > > > > > > > > > > From fryhle@u.washington.edu Fri Apr 18 11:02:01 1997 Received: from jason03.u.washington.edu (jason03.u.washington.edu [140.142.77.10]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id LAA05526 for ; Fri, 18 Apr 1997 11:02:01 -0700 Received: from homer04.u.washington.edu (homer04.u.washington.edu [140.142.76.11]) by jason03.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id KAA15536 for ; Fri, 18 Apr 1997 10:58:27 -0700 Received: from localhost (fryhle@localhost) by homer04.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id KAA21864 for ; Fri, 18 Apr 1997 10:58:27 -0700 Date: Fri, 18 Apr 1997 10:58:26 -0700 (PDT) From: Craig Fryhle To: Organic Chemistry I List Subject: Learning Group Presentation Schedule Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII This morning I passed out the Learning Group Problem for Chapter 13. The groups that should prepare to present this problem will be the groups listed on the handout from today, not the ones listed on the schedule in the class syllabus. The syllabus schedule has the group numbers preparing for Chapter 13 and Chapter 11 problems reversed. Sorry about the confusion. CBF ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From taylormr@plu.edu Fri Apr 18 11:33:46 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id LAA05768 for ; Fri, 18 Apr 1997 11:33:46 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHUL2I3XPG003FTT@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 18 Apr 1997 11:30:10 PDT Date: Fri, 18 Apr 1997 11:30:10 -0700 (PDT) From: "M.Taylor" Subject: learning groups 14 and 18 To: ORGANIC CHEMISTRY Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII For the formal lab report, Dr. Fryhle combined groups 14 and 18. Who are the people in group 18, and which requests did you turn in to do? Group 14, Justin and I requested to do the isopentyl acetate, the acetylsalicylic acid, and the R (+) carvone, and S (-) carvone. Hopefully early next week, we can all get together and work on the report. Hope to see you all then. Also, you can e-mail me at taylormr. Talk to you later. Michele From fryhle@u.washington.edu Fri Apr 18 14:13:29 1997 Received: from jason01.u.washington.edu (jason01.u.washington.edu [140.142.70.24]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id OAA06644 for ; Fri, 18 Apr 1997 14:13:28 -0700 Received: from homer18.u.washington.edu (homer18.u.washington.edu [140.142.76.2]) by jason01.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id OAA04684 for ; Fri, 18 Apr 1997 14:09:55 -0700 Received: from localhost (fryhle@localhost) by homer18.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id OAA59944 for ; Fri, 18 Apr 1997 14:09:54 -0700 Date: Fri, 18 Apr 1997 14:09:54 -0700 (PDT) From: Craig Fryhle To: Organic Chemistry I List Subject: Exam II Multiple Choice Scores Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings, everyone. I have graded the multiple choice section of the second exam and posted the scores in the Organic Chemistry glass display case. The average was 70 on the multiple choice section. The other part is not graded yet. CBF ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From youngcf@plu.edu Fri Apr 18 15:43:09 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA07298 for ; Fri, 18 Apr 1997 15:43:08 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHUTRN9YE8003JKI@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 18 Apr 1997 15:39:31 PDT Date: Fri, 18 Apr 1997 15:39:30 -0700 (PDT) From: youngcf@plu.edu Subject: Formal reports To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII GROUP4: Please contact me at x7950 over the weekend or by Monday so we can discuss the parts each person will play in the report. Also, we need to meet Sunday in order to do the learning group problem. ( chpt.13) Even if we are not supposed to present, we need to be ready for any changes. Youngcf@plu.edu. From youngcf@plu.edu Fri Apr 18 15:46:32 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA07424 for ; Fri, 18 Apr 1997 15:46:31 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHUTVRI06E003JKI@plu.edu> for ORGANIC1@rainier.chem.plu.edu; Fri, 18 Apr 1997 15:42:50 PDT Date: Fri, 18 Apr 1997 15:42:50 -0700 (PDT) From: youngcf@plu.edu Subject: IR spectrum To: ORGANIC1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII HELP: I know that the bond strengths for C-C bonds are determined by the hybridizations, but does it matter if it is bonded to a functional group that is highly polarized? Youngcf@plu.edu. From fryhle@u.washington.edu Fri Apr 18 17:06:42 1997 Received: from jason02.u.washington.edu (jason02.u.washington.edu [140.142.76.8]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id RAA08203 for ; Fri, 18 Apr 1997 17:06:42 -0700 Received: from homer29.u.washington.edu (homer29.u.washington.edu [140.142.76.14]) by jason02.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id RAA14006 for ; Fri, 18 Apr 1997 17:03:08 -0700 Received: from localhost (fryhle@localhost) by homer29.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id RAA27266 for ; Fri, 18 Apr 1997 17:03:08 -0700 Date: Fri, 18 Apr 1997 17:03:07 -0700 (PDT) From: Craig Fryhle To: Organic Chemistry I List Subject: Learning Group Problem - Chapter 13 Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Learning Group Problem Chapter 13 Groups 1, 4, 12, and 19 prepare to present parts Ia and IIa below. Groups 3, 6, 18, and 22 prepare to present parts Ib and IIb below. ***** I. Two compounds (A and B) with the molecular formula C10H15N have the following IR and 13C NMR data. Both compounds are soluble in dilute HCl. Elucidate the structure of these two compounds and interpret the spectra. I suggest making a sketch of each NMR spectrum. a. The IR spectrum for compound A shows two bands in the 3300-3500 cm-1 region. The broad band proton-decoupled 13C NMR spectrum displayed the following signals (information from the DEPT 13C spectrum is given in parentheses with the 13C chemical shifts): 13C NMR: 140 (C), 127 (C), 125 (CH), 118 (CH), 24 (CH2), 13 (CH3). b. The IR spectrum for compound B shows no bands in the 3300-3500 cm-1 region. The broad band proton-decoupled 13C NMR spectrum displayed the following signals (information from the DEPT 13C spectrum is given in parentheses with the 13C chemical shifts): 13C NMR: 147 (C), 129 (CH), 115 (CH), 111 (CH), 44 (CH2), 13(CH3) II. Two compounds with the molecular formula C5H10O have the following 1H and 13C NMR data. Both compounds have IR absorption bands in the 1700-1720 cm-1 region. Elucidate the structure of these two compounds and interpret the spectra. I suggest making a sketch of each NMR spectrum. a. 1H NMR: 2.55 (septet, 1 H), 2.10 (singlet, 3H), 1.05 (doublet, 6H) 13C NMR: 212.6, 41.5, 27.2, 17.8 b. 1H NMR: 2.38 (triplet, 2H), 2.10 (singlet, 3H), 1.57 (sextet, 2H), 0.88 (triplet, 3H) 13C NMR: 209.0, 45.5, 29.5, 17.0, 13.2 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From fryhle@u.washington.edu Fri Apr 18 17:58:43 1997 Received: from jason01.u.washington.edu (jason01.u.washington.edu [140.142.70.24]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id RAA08538 for ; Fri, 18 Apr 1997 17:58:43 -0700 Received: from homer27.u.washington.edu (homer27.u.washington.edu [140.142.77.7]) by jason01.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id RAA12794 for ; Fri, 18 Apr 1997 17:55:09 -0700 Received: from localhost (fryhle@localhost) by homer27.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id RAA82856 for ; Fri, 18 Apr 1997 17:55:09 -0700 Date: Fri, 18 Apr 1997 17:55:09 -0700 (PDT) From: Craig Fryhle To: Organic Chemistry I List Subject: Topic Assignments - Formal Lab Report Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Topic Assignments for the Formal Lab Report Lab Group Numbers --------------------------------- -------------------- I. Acetylsalicylic Acid (Expt. 2) 9, 17, 21 II. TLC Analysis of Drugs (Expt. 4) 5, 6 III. Syn. of Isopentyl Acetate (Ban. Oil) (Expt. 6) 1, 22 IV. Isolation of Eugenol From Cloves (Expt. 7) 4, 13, 20 V. Stereochemistry - Spearmint and Caraway Oil 16, 19 VI. Reactivities of Alkyl Halides (Expt. 10) 14-18, 15 VII. Synthesis of t-Pentyl Chloride (Expt. 13) 2, 8 VIII. Dehydration of Methylcyclohexanol (Expt. 15) 3, 7, 10 IX. Bromohydrin Experiment 11, 12 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From fryhle@u.washington.edu Fri Apr 18 21:48:19 1997 Received: from jason01.u.washington.edu (jason01.u.washington.edu [140.142.70.24]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA09681 for ; Fri, 18 Apr 1997 21:48:19 -0700 Received: from homer01.u.washington.edu (homer01.u.washington.edu [140.142.70.11]) by jason01.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id VAA13202 for ; Fri, 18 Apr 1997 21:44:45 -0700 Received: from localhost (fryhle@localhost) by homer01.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id VAA95730 for ; Fri, 18 Apr 1997 21:44:45 -0700 Date: Fri, 18 Apr 1997 21:44:44 -0700 (PDT) From: Craig Fryhle To: Organic Chemistry I List Subject: Group Clarification Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII In order for there to be no misinterpretations, the following line copied from the recently sent group report assignment message means that group 14 and group 18 work together, not that group 14 through 18 are all assigned this experiment. I should have written it "14 with 18". > VI. Reactivities of Alkyl Halides (Expt. 10) 14-18, 15 Have a good weekend. CBF ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From blackkl@plu.edu Sun Apr 20 16:57:31 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA22478 for ; Sun, 20 Apr 1997 16:57:30 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHXOYJXSQO003WR2@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 20 Apr 1997 16:53:53 PDT Date: Sun, 20 Apr 1997 16:53:53 -0700 (PDT) From: blackkl@plu.edu Subject: Group 4... To: Organic Chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Hello there..does anyone in group 4 know if we are meeting tonight to do our learning group problem or if not tonight when we are going to meet? I have to work until 9pm tonight but just let me know what is going on..Thanks! Kristey From schelvac@plu.edu Sun Apr 20 17:06:33 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id RAA22547 for ; Sun, 20 Apr 1997 17:06:33 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHXP9RR3O6003PJX@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 20 Apr 1997 17:02:56 PDT Date: Sun, 20 Apr 1997 17:02:56 -0700 (PDT) From: schelvac@plu.edu Subject: carbocations To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I had some questions about carbocations. Do products of any reaction always form towards the higher carbocation (ie. formation of a tertiary carbocation over a primary carbocation)? And does the formation of a tertiary carbocation always have a lower free energy? Thanks, Alethea From bobbtl@plu.edu Sun Apr 20 18:31:43 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id SAA22985 for ; Sun, 20 Apr 1997 18:31:42 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHXS9A668W0043UZ@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 20 Apr 1997 18:28:03 PDT Date: Sun, 20 Apr 1997 18:28:02 -0700 (PDT) From: bobbtl@plu.edu Subject: Re: carbocations In-reply-to: To: schelvac@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Yes, the higher carbocation is always favored. An alkanide ion or hydride ion will usually undergo rearrangement if this will lead to the formation of a more stable tertiary carbocation. The reaction will always choose the most stable carbocation, unless a bulky base is used. I hope this clears things up. On Sun, 20 Apr 1997 schelvac@plu.edu wrote: > I had some questions about carbocations. Do products of any reaction > always form towards the higher carbocation (ie. formation of a tertiary > carbocation over a primary carbocation)? And does the formation of a > tertiary carbocation always have a lower free energy? > > Thanks, > Alethea > > From bobbtl@plu.edu Mon Apr 21 22:46:07 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA02146 for ; Mon, 21 Apr 1997 22:46:06 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHZFEZHW4000574V@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 21 Apr 1997 22:42:24 PDT Date: Mon, 21 Apr 1997 22:42:24 -0700 (PDT) From: bobbtl@plu.edu Subject: problem 13.5(b) To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Why would the two hydrogens attached to the -CH2CH3 be considered chemically different? Does it have to do with the fact that sec-butyl alcohol is found as enantiomers? Terra From charbogd@plu.edu Mon Apr 21 23:11:05 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id XAA02272 for ; Mon, 21 Apr 1997 23:11:04 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHZGAV7HAO005EMR@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 21 Apr 1997 23:07:20 PDT Date: Mon, 21 Apr 1997 23:07:19 -0700 (PDT) From: "Gabriel D. Charbonneau" Subject: Learning Group 13 part I b To: Organic Chemlist Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I was wondering if there is more information nescessary that may make part I b of this week's learning group plausible to figure out. I know the Nitrogen cannot be an amine and therefore must be a nitrile group. There must be at least one methyl group and one CH2 also. As for the three different CH groups, they suggest a benzyl ring, however that doesn't leave enough places to use up the nescessary 15 hydrogens. If the CH groups are simply doubble bonds, it seems impossible to put them together so that each would represent a different peak on the CNMR. gabe From petershm@plu.edu Tue Apr 22 01:34:58 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id BAA03308 for ; Tue, 22 Apr 1997 01:34:57 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IHZLBD7R5C005B3D@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 22 Apr 1997 01:31:16 PDT Date: Tue, 22 Apr 1997 01:31:16 -0700 (PDT) From: petershm@plu.edu In-reply-to: To: "Gabriel D. Charbonneau" Cc: Organic Chemlist Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII If two different kinds of carbon groups are found within the same range, how are we supposed to determine which peak is which? Ex. Alkyne found at 60-90 and alcohol or ether found at 50-90. pp.575 From sounthna@plu.edu Tue Apr 22 09:11:45 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id JAA05604 for ; Tue, 22 Apr 1997 09:11:44 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II019Q6S4W005IZX@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 22 Apr 1997 09:08:04 PDT Date: Tue, 22 Apr 1997 09:08:04 -0700 (PDT) From: sounthna@plu.edu Subject: Group 9: Formal Report To: Questions!!! Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Hey Chad, Andy this is Nope. What what is a good time to meet for you guys. Today after 5pm be good or Wed. after 3 would be good as well. Nope From frickeje@plu.edu Tue Apr 22 11:53:15 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id LAA06462 for ; Tue, 22 Apr 1997 11:53:14 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II06WV2BLC005F43@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 22 Apr 1997 11:49:32 PDT Date: Tue, 22 Apr 1997 11:49:31 -0700 (PDT) From: frickeje@plu.edu Subject: Formal Report: Learning Group 5 To: Organic Chemistry List Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII To LG # 5, Let's meet at 3:30 today to figure out what sections are going to be covered by who for the formal report. See you all then. -John From fryhle@u.washington.edu Tue Apr 22 11:56:37 1997 Received: from jason04.u.washington.edu (jason04.u.washington.edu [140.142.78.5]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id LAA06500 for ; Tue, 22 Apr 1997 11:56:36 -0700 Received: from homer07.u.washington.edu (homer07.u.washington.edu [140.142.77.11]) by jason04.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id LAA17634; Tue, 22 Apr 1997 11:52:58 -0700 Received: from localhost (fryhle@localhost) by homer07.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id LAA100448; Tue, 22 Apr 1997 11:52:57 -0700 Date: Tue, 22 Apr 1997 11:52:57 -0700 (PDT) From: Craig Fryhle To: petershm@plu.edu cc: "Gabriel D. Charbonneau" , Organic Chemlist Subject: Overlapping Chemical Shift Ranges In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings. This is one example where fitting pieces of the puzzle together using information from the IR and molecular formula is helpful. If you have oxyen in the formula, IR can tell you whether you have an alcohol or an ether. If there is no oxygen, then an alkyne seemes plausible. IR might not readily help you distinguish an ether from an internal alkyne, but 1H NMR can help. (A terminal alkyne would have the alkyne C-H stretch in a readily recognized part of the IR spectrum). Regarding an internal alkyne vs. an ether, the 1H NMR chemical shift of hydrogens on a carbon of the ether functional group would strongly indicate that group vs. the alkyne. There is a bit of detective work in solving structures using spectroscopic data. One evaluates clues given by each piece of evidence. It will frequently be the case that clues from more than one type of spectroscopic data is necessary. For organic compounds, NMR (13C and 1H) is usually teamed with IR. Mass spectroscopy is also very helpful, and I wish we had time to discuss it, but I'll have to leave that to interested readers who ponder Mass Spectroscopy in the Special Topic in the text. Cheerio, CBF On Tue, 22 Apr 1997 petershm@plu.edu wrote: > If two different kinds of carbon groups are found within the same range, > how are we supposed to determine which peak is which? Ex. Alkyne found at > 60-90 and alcohol or ether found at 50-90. pp.575 > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From larsenak@plu.edu Tue Apr 22 21:28:47 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA09582 for ; Tue, 22 Apr 1997 21:28:45 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II0Q2ZPUYO005QG6@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 22 Apr 1997 20:58:05 PDT Date: Tue, 22 Apr 1997 20:58:05 -0700 (PDT) From: larsenak@plu.edu Subject: Re: Group 9: Formal Report In-reply-to: To: sounthna@plu.edu Cc: Questions!!! Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Nope, Wednesday after 6 sounds like a good time to meet. Andy On Tue, 22 Apr 1997 sounthna@plu.edu wrote: > > Hey Chad, Andy this is Nope. What what is a good time to meet for you > guys. Today after 5pm be good or Wed. after 3 would be good as well. > > > Nope > > From larsenak@plu.edu Wed Apr 23 00:52:23 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id AAA10950 for ; Wed, 23 Apr 1997 00:52:22 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II0Y2P3BHS005OAX@plu.edu> for Organic1@rainier.chem.plu.edu; Wed, 23 Apr 1997 00:46:54 PDT Date: Wed, 23 Apr 1997 00:46:54 -0700 (PDT) From: larsenak@plu.edu To: Organic Chemistry 232 Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII When is the formal lab report due? Also, when are we going to able to start working on the next lab? A.L. From craigtm@plu.edu Wed Apr 23 07:46:39 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id HAA12966 for ; Wed, 23 Apr 1997 07:46:38 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II1CLIPOOG005MVM@plu.edu> for Organic1@rainier.chem.plu.edu; Wed, 23 Apr 1997 07:42:57 PDT Date: Wed, 23 Apr 1997 07:42:57 -0700 (PDT) From: craigtm@plu.edu Subject: Re: your mail In-reply-to: To: larsenak@plu.edu Cc: Organic Chemistry 232 Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII A.L., the formal lab report is due May 3, I believe. It tells in our lab sylabous. He mentioned something about putting our next lab out at the beginning of next week (early) but if he doesn't then we won't be able to start working on it until 2 weeks from now. Tiffany On Wed, 23 Apr 1997 larsenak@plu.edu wrote: > When is the formal lab report due? Also, when are we going to able to > start working on the next lab? > A.L. > > From fryhle@u.washington.edu Wed Apr 23 09:50:16 1997 Received: from jason01.u.washington.edu (jason01.u.washington.edu [140.142.70.24]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id JAA13674 for ; Wed, 23 Apr 1997 09:50:16 -0700 Received: from homer06.u.washington.edu (homer06.u.washington.edu [140.142.76.13]) by jason01.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id JAA20736 for ; Wed, 23 Apr 1997 09:46:36 -0700 Received: from localhost (fryhle@localhost) by homer06.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id JAA66900 for ; Wed, 23 Apr 1997 09:46:36 -0700 Date: Wed, 23 Apr 1997 09:46:35 -0700 (PDT) From: Craig Fryhle To: Organic Chemistry I List Subject: Chemistry Banquet Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings, everyone. I want to pass on an invitation to you to attend the chemistry banquet on Monday evening May 5. It is free and will be held in the Regency Room of the UC. Awards and scholarships will be presented. Please sign up at the stockroom window so that we know how many to expect. Cheers, CBF ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From fryhle@u.washington.edu Wed Apr 23 09:54:55 1997 Received: from jason01.u.washington.edu (jason01.u.washington.edu [140.142.70.24]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id JAA13718 for ; Wed, 23 Apr 1997 09:54:54 -0700 Received: from homer06.u.washington.edu (homer06.u.washington.edu [140.142.76.13]) by jason01.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id JAA13438 for ; Wed, 23 Apr 1997 09:51:15 -0700 Received: from localhost (fryhle@localhost) by homer06.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id JAA80200 for ; Wed, 23 Apr 1997 09:51:14 -0700 Date: Wed, 23 Apr 1997 09:51:14 -0700 (PDT) From: Craig Fryhle To: Organic Chemistry I List Subject: Exams and Grignard Experiment Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Hello, folks. Exams (written and multiple choice parts) are available at the stockroom window during Open Lab hours, if you have your ID card with you. We will have supplies available next week for the last Experiment (the Grignard reaction). So, you may begin that lab a week early, if you choose. Supplies will be available the following week, too. I'll post an announcement with some tips and hints for the Grignard lab in the coming days. As I mentioned, it requires your careful attention to experimental technique and is a little longer than some of the other labs. This one is more like the length all organic labs used to be. Ciao for now, CBF ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From taylormr@plu.edu Wed Apr 23 10:06:34 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id KAA13823 for ; Wed, 23 Apr 1997 10:06:33 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II1HGQT48G005SOZ@plu.edu> for Organic1@rainier.chem.plu.edu; Wed, 23 Apr 1997 10:02:41 PDT Date: Wed, 23 Apr 1997 10:02:39 -0700 (PDT) From: "M.Taylor" Subject: Re: your mail In-reply-to: To: larsenak@plu.edu Cc: Organic Chemistry 232 Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Formal labs are due May 2., also Dr. Fryhle said that he would try and open up the last lab next week a week early. Michele On Wed, 23 Apr 1997 larsenak@plu.edu wrote: > When is the formal lab report due? Also, when are we going to able to > start working on the next lab? > A.L. > > From hiattzr@plu.edu Wed Apr 23 11:34:34 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id LAA14333 for ; Wed, 23 Apr 1997 11:34:29 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II1IWG7TLY005NE7@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 23 Apr 1997 10:43:45 PDT Date: Wed, 23 Apr 1997 10:43:39 -0700 (PDT) From: hiattzr@plu.edu Subject: L.G. chap 13 To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII To Dr. Fryhle or whoever else can answer this question, Could the information given about the unknown compound being soluble in dilute HCl also be telling us that there are double bonds present in the unknown compound. If double bonds are present, wouldnt acid catalyzed hydration of the alkene occur (see section 8.5 in Solomons), adding a hydroxyl group to one end of each double bond. Each of these hydroxyl groups would cause the unknown compound to become more polar and interact with the polar solvent, H2O, through hydrogen bonding and dipole-dipole interactions. Could this info. be used as further proof (along with the C13 NMR info given) that the unknown compound contains double bonds? Just curious. Zach From larsenak@plu.edu Wed Apr 23 12:48:33 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id MAA14810 for ; Wed, 23 Apr 1997 12:48:32 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II1N4I66Y80063IK@plu.edu> for Organic1@rainier.chem.plu.edu; Wed, 23 Apr 1997 12:44:36 PDT Date: Wed, 23 Apr 1997 12:44:36 -0700 (PDT) From: larsenak@plu.edu Subject: Carbon-13 NMR To: Organic Chemistry 232 Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII If the heights of the peaks in the carbon-13 NMR spectra don't tell how many carbon atoms are of that type. What do the heights of these peaks tell us if anything? A.L. From bowersmy@plu.edu Wed Apr 23 13:09:38 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id NAA14945 for ; Wed, 23 Apr 1997 13:09:37 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II1NUXY3TI0065WF@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 23 Apr 1997 13:05:54 PDT Date: Wed, 23 Apr 1997 13:05:54 -0700 (PDT) From: bowersmy@plu.edu Subject: lab report To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII In the paper describing the formal lab report it said that source and purity of chemicals should be noted. I was wondering where i would get that information. From bowersmy@plu.edu Wed Apr 23 14:00:56 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id OAA15251 for ; Wed, 23 Apr 1997 14:00:55 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II1PNJ5G9C0063U1@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 23 Apr 1997 13:57:12 PDT Date: Wed, 23 Apr 1997 13:57:11 -0700 (PDT) From: bowersmy@plu.edu Subject: formal report To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII In the formal report for acetylsalicylic acid does the test comparing acetylsalicylic acid with comercial aspirin need to be included? From fryhle@u.washington.edu Wed Apr 23 14:33:35 1997 Received: from jason04.u.washington.edu (jason04.u.washington.edu [140.142.78.5]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id OAA15478 for ; Wed, 23 Apr 1997 14:33:34 -0700 Received: from homer35.u.washington.edu (homer35.u.washington.edu [140.142.78.18]) by jason04.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id OAA10748; Wed, 23 Apr 1997 14:29:54 -0700 Received: from localhost (fryhle@localhost) by homer35.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id OAA19386; Wed, 23 Apr 1997 14:29:54 -0700 Date: Wed, 23 Apr 1997 14:29:54 -0700 (PDT) From: Craig Fryhle To: bowersmy@plu.edu cc: organic1 Subject: Re: lab report In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Well, in a situation where you may have gathered the reagents yourself, as in a research or industrial lab, you would know the manufacturer's stated purity and any additional purifications you may have done. In this case, since we supply the reagents in secondary containers for your use in the open lab, about all you can say is that they were provided by the Department of Chemistry Stockroom, and that they are assumed to be of sufficient purity for use in this experiment. CBF On Wed, 23 Apr 1997 bowersmy@plu.edu wrote: > In the paper describing the formal lab report it said that source and > purity of chemicals should be noted. I was wondering where i would get > that information. > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From fryhle@u.washington.edu Wed Apr 23 16:20:01 1997 Received: from jason01.u.washington.edu (jason01.u.washington.edu [140.142.70.24]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA16120 for ; Wed, 23 Apr 1997 16:20:00 -0700 Received: from homer15.u.washington.edu (homer15.u.washington.edu [140.142.70.16]) by jason01.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id QAA11624; Wed, 23 Apr 1997 16:16:20 -0700 Received: from localhost (fryhle@localhost) by homer15.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id QAA37078; Wed, 23 Apr 1997 16:16:20 -0700 Date: Wed, 23 Apr 1997 16:16:19 -0700 (PDT) From: Craig Fryhle To: hiattzr@plu.edu cc: organic1 Subject: Re: L.G. chap 13 In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Yes, I think this is a reasonable proposal. I'd be inclined to think first of amines, though, given that there was nitrogen in the molecular formula. But, yes, the hydration of an alkene would make a compound more polar, and potentially water soluble. Good idea! CBF On Wed, 23 Apr 1997 hiattzr@plu.edu wrote: > To Dr. Fryhle or whoever else can answer this question, > > Could the information given about the unknown compound being > soluble in dilute HCl also be telling us that there are double bonds > present in the unknown compound. If double bonds are present, wouldnt > acid catalyzed hydration of the alkene occur (see section 8.5 in > Solomons), > adding a hydroxyl group to one end of each double bond. Each of these > hydroxyl groups would cause the unknown compound to become more > polar and interact with the polar solvent, H2O, through hydrogen bonding > and dipole-dipole interactions. Could this info. be used as further proof > (along with the C13 NMR info given) that the unknown compound contains > double bonds? Just curious. > > Zach > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From fryhle@u.washington.edu Wed Apr 23 16:40:44 1997 Received: from jason03.u.washington.edu (jason03.u.washington.edu [140.142.77.10]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id QAA16259 for ; Wed, 23 Apr 1997 16:40:44 -0700 Received: from homer15.u.washington.edu (homer15.u.washington.edu [140.142.70.16]) by jason03.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id QAA15430; Wed, 23 Apr 1997 16:37:04 -0700 Received: from localhost (fryhle@localhost) by homer15.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id QAA97206; Wed, 23 Apr 1997 16:37:03 -0700 Date: Wed, 23 Apr 1997 16:37:03 -0700 (PDT) From: Craig Fryhle To: larsenak@plu.edu cc: Organic Chemistry 232 Journal Club Subject: Re: Carbon-13 NMR In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII One can hazard a few assumptions based on the height of peaks in carbon-13 NMR spectra, and these can be useful in interpreting spectra if applied with judgement. 1) For equivalent carbons the signal for those carbons would be taller than a signal for a single unique carbon of comparable environment. For example, when three carbons are equivalent, as in a tert-butyl group, the signal for those equivalent carbons would be taller than for a single carbon of identical type. 2) It is true that signals for carbons with hydrogens attached are generally taller than signals for carbons without any hydrogens. The effect is most dramatic in the case of no hydrogens vs. any hydrogens (1,2, or 3). Take for example a carbonyl carbon signal (except for alddehydes), vs. any carbon that has hydrogens attached. Carbonyl carbons always give small peaks. There is not any appreciable difference between carbons with 1, 2, or 3 hydrogens. The reasons for this has to do with the way energy can be released by the carbon once it has been excited in the NMR (relaxation, as it is called). The same effect is true for a quaternary alkyl carbon vs. an alkyl carbon that has hydrogens attached. Quaternary carbons always give small signals. But in general, one can't *quantitatively* correlate the height of carbon-13 NMR signals with the number of carbons a signal represents, as we do with proton NMR, unless very special instrumental techniques are used, and these are not generally applied in routine spectra. CBF On Wed, 23 Apr 1997 larsenak@plu.edu wrote: > If the heights of the peaks in the carbon-13 NMR spectra don't tell how > many carbon atoms are of that type. What do the heights of these peaks > tell us if anything? > A.L. > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From larsenak@plu.edu Wed Apr 23 18:13:46 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id SAA16851 for ; Wed, 23 Apr 1997 18:13:46 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II1YHUO1RK006TM4@plu.edu> for Organic1@rainier.chem.plu.edu; Wed, 23 Apr 1997 18:09:57 PDT Date: Wed, 23 Apr 1997 18:09:56 -0700 (PDT) From: larsenak@plu.edu To: Organic Chemistry 232 Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Chad, Where are you? Nope and me are at Rieke trying to put together a formal lab report. Give us a call or an E-mail please. Thanks, Andy and Nope From larsenak@plu.edu Wed Apr 23 18:26:58 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id SAA16968 for ; Wed, 23 Apr 1997 18:26:57 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II1YYEDQ80006CO3@plu.edu> for Organic1@rainier.chem.plu.edu; Wed, 23 Apr 1997 18:23:16 PDT Date: Wed, 23 Apr 1997 18:23:15 -0700 (PDT) From: larsenak@plu.edu To: Organic Chemistry 232 Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII How long does the formal lab report have to be? A.L. From chaputcl@plu.edu Wed Apr 23 20:08:00 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA17557 for ; Wed, 23 Apr 1997 20:07:59 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II22HBLV1C006TGO@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 23 Apr 1997 20:04:04 PDT Date: Wed, 23 Apr 1997 20:04:03 -0700 (PDT) From: chaputcl@plu.edu Subject: Group 17 To: Organic Chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII We need to get together and discuss this lab report before this weekend!!! Call me Chris From fryhle@u.washington.edu Wed Apr 23 22:11:52 1997 Received: from jason04.u.washington.edu (jason04.u.washington.edu [140.142.78.5]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA18221 for ; Wed, 23 Apr 1997 22:11:51 -0700 Received: from homer31.u.washington.edu (homer31.u.washington.edu [140.142.78.17]) by jason04.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id WAA16262 for ; Wed, 23 Apr 1997 22:08:12 -0700 Received: from localhost (fryhle@localhost) by homer31.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id WAA55434 for ; Wed, 23 Apr 1997 22:08:12 -0700 Date: Wed, 23 Apr 1997 22:08:12 -0700 (PDT) From: Craig Fryhle To: Organic Chemistry I List Subject: Learning Group Problem - Chapter 9 Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Hi, folks. Here are the Learning Group Problems for Chapter 9. I'll have hard copies outside my door on Thursday afternoon and in class on Friday. ------------------ Learning Group Problems - Chapter 9 ***** Groups 7, 8, 14, and 15 prepare to present questions 1a, 2 (retrosynthetic analysis only), and 3 below. Groups 16, 17, 19, and 20 prepare to present questions 1b, 2 (synthesis only), and 3 below. ***** It behooves the entire class to work on the learning group problems. 1. a) Draw structures for the organic products that would result when an excess of trans-1,2- dimethylcyclohexane reacts with Br2 in the presence of heat and light. Use three-dimensional formulas to show stereochemistry. If possible, indicate which product(s) would be expected to predominate. b) Draw structures for the organic products that would result when an excess of trans-1,2- dimethylcyclohexane reacts with Cl2 in the presence of heat and light. Use three-dimensional formulas to show stereochemistry. If possible, indicate which product(s) would be expected to predominate. 2. Propose a synthesis of chloroethene (vinyl chloride) from ethane. More than one step will be necessary. Ethane must be the sole source of carbon atoms, but you may use any other additional reagents necessary. Devise a retrosynthetic analysis first. 3. Chloroethene (vinyl chloride) will form a polymer known as polyvinylchloride (PVC) when treated with a radical initiator. Write the structure of this well-known polymer and a mechanism for the polymerization reaction assuming a radical mechanism intitiated by a generic alkyl radical R "dot" (an alkyl group with an unpaired electron). ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From baileyle@plu.edu Thu Apr 24 11:28:47 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id LAA22753 for ; Thu, 24 Apr 1997 11:28:47 -0700 Received: from Hind215b.PLU.EDU by plu.edu (PMDF V5.1-5 #17589) with SMTP id <01II2YN7OXSU006Z7J@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 24 Apr 1997 11:25:02 PDT Date: Thu, 24 Apr 1997 11:23:41 -0700 From: Lora Bailey Subject: Re: Learning Group Problem - Chapter 9 To: organic1, Craig Fryhle Reply-to: baileyle@plu.edu Message-id: <335FA52D.1FB0@plu.edu> MIME-version: 1.0 X-Mailer: Mozilla 3.01 (Win95; I) Content-type: text/plain; charset=us-ascii Content-transfer-encoding: 7bit References: Professor, I'm in group 2, and we're scheduled to present chapter 9, but we aren't on the list of groups on the email you sent. Which part of the problem are we supposed to prepare? Lora Bailey From fryhle@u.washington.edu Thu Apr 24 20:24:58 1997 Received: from jason05.u.washington.edu (jason05.u.washington.edu [140.142.78.6]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA05051 for ; Thu, 24 Apr 1997 20:24:57 -0700 Received: from homer14.u.washington.edu (homer14.u.washington.edu [140.142.70.15]) by jason05.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id UAA13044 for ; Thu, 24 Apr 1997 20:21:17 -0700 Received: from localhost (fryhle@localhost) by homer14.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id UAA80904 for ; Thu, 24 Apr 1997 20:21:17 -0700 Date: Thu, 24 Apr 1997 20:21:17 -0700 (PDT) From: Craig Fryhle Reply-To: Craig Fryhle To: Organic Chemistry I List Subject: Schedule and Corrected Group #'s - LGP Ch. 9 Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Hi, class. Sorry that I again confused the group numbers scheduled to present. I think we had best stick to the group numbers published in the syllabus as the ones that are scheduled to present for chapter 9. Those groups are 1,2,3,9,12, 15, 17, and 21. Below I have sent you the problem again, with the corrected group assignments. Also, I think we should have the Chapter 9 LGP's on Wednesday of next week, instead of Monday. That will accomodate some of the confusion on group scheduling and allow a more typical time frame for the LGP, since Chapter 9 has only two days coverage on the Syllabus. What that means is that we'll have the following schedule: Friday 4/25 Chapter 9, w/Quiz Monday 4/28 Chapter 10 (but Quiz on Wed. 4/30) Wed. 4/30 Chapter 9, w/ Learning Group Presentations and Ch 10 Quiz Friday 5/1 Chapter 10 Monday 5/4 Chapter 10 LGP Wed. 5/6 Exam 3 etc. ------------------ Learning Group Problems - Chapter 9 ***** Groups 2,3, 12, and 17 prepare to present questions 1a, 2 (retrosynthetic analysis only), and 3 below. Groups 1, 9, 15, and 21 prepare to present questions 1b, 2 (synthesis only), and 3 below. ***** It behooves the entire class to work on the learning group problems. 1. a) Draw structures for the organic products that would result when an excess of trans-1,2- dimethylcyclohexane reacts with Br2 in the presence of heat and light. Use three-dimensional formulas to show stereochemistry. If possible, indicate which product(s) would be expected to predominate. b) Draw structures for the organic products that would result when an excess of trans-1,2- dimethylcyclohexane reacts with Cl2 in the presence of heat and light. Use three-dimensional formulas to show stereochemistry. If possible, indicate which product(s) would be expected to predominate. 2. Propose a synthesis of chloroethene (vinyl chloride) from ethane. More than one step will be necessary. Ethane must be the sole source of carbon atoms, but you may use any other additional reagents necessary. Devise a retrosynthetic analysis first. 3. Chloroethene (vinyl chloride) will form a polymer known as polyvinylchloride (PVC) when treated with a radical initiator. Write the structure of this well-known polymer and a mechanism for the polymerization reaction assuming a radical mechanism intitiated by a generic alkyl radical R "dot" (an alkyl group with an unpaired electron). ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From fryhle@u.washington.edu Fri Apr 25 12:16:04 1997 Received: from jason05.u.washington.edu (jason05.u.washington.edu [140.142.78.6]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id MAA10502 for ; Fri, 25 Apr 1997 12:16:03 -0700 Received: from homer07.u.washington.edu (homer07.u.washington.edu [140.142.77.11]) by jason05.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id MAA15726 for ; Fri, 25 Apr 1997 12:12:22 -0700 Received: from localhost (fryhle@localhost) by homer07.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id MAA35860 for ; Fri, 25 Apr 1997 12:12:22 -0700 Date: Fri, 25 Apr 1997 12:12:22 -0700 (PDT) From: Craig Fryhle To: Organic Chemistry I List Subject: Grignard Experiment Information Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Hi, folks. Here is the handout I've prepared for the Grignard experiment. Hard copies are at the stockroom window. *************** Grignard Synthesis of Benzoic Acid (Expt. 25B, Pavia, et al) Supplementary Information This experiment requires you to pay very careful attention to experimental detail. It is imperative that you read the entire protocol and mentally rehearse the procedures you will carry out. Much of the experiment must be conducted under anhydrous conditions using oven-dried equipment. It is important that you plan ahead to orchestrate efficient use of the equipment provided. You will probably need part of a second period in the lab to complete the experiment. Here are a few tips and highlights of the procedure, more or less in the order in which they will be important to you. This is not a step by step description of the procedure, however. Use this information together with your lab text. Read the procedure thoroughly and make a list of all the equipment that must be dried in a lab oven. If any of the glassware that must be dry is visibly wet when you receive it, rinse it with acetone before placing it in the oven. Put the acetone rinsings in the non-halogenated waste container. Put all of the equipment that must be dry inside the 250 mL beaker provided and place it in the oven for 20-30 minutes. If you are provided a glass syringe (vs. plastic) for use during the experiment, dry it in the oven with the plunger removed from the barrel. Do not place plastic syringes in the oven. Label the beaker with your name. Be sure the syringe needle you are given is dry on the inside. Since you will probably be given a needle with a plastic attachment point, do not place it in the oven. Instead, force a little acetone through the needle using an acetone squirt bottle, followed by a gentle stream of air to evaporate the acetone. It is disastrous for a Grignard reaction to use a needle that has water trapped inside it. You will be provided one 5-mL conical vial for the reaction, one approximately 5 mL ordinary vial for storage of anhydrous ether, and one approximately 3-mL ordinary vial for storage of the bromobenzene solution. These vials must be dried in the oven along with the other equipment. The two ordinary vials can be used later for storage of the reaction mixture at the specified stopping point and for submission of the sample for grading. When you remove the equipment from the oven (after 20-30 minutes) assemble the various items as soon as they are cool enough to handle (cap the vials, assemble the syringe, build the reaction apparatus). Be sure to put the drying tube on the reaction setup. The most important factor contributing to a successful experiment is extreme attention to exclusion of moisture from all sources (until the hydrolysis step). Examples of Pasteur pipets calibrated for 0.5 and 1.0 mL delivery volumes will be displayed by the stockroom window. You can use these as guides to prepare your own calibrated pipets. When scraping and cutting the magnesium use tweezers to hold the strips. Do not touch the magnesium with your fingers, due to the moisture on your skin. If you pay careful attention to the instructions and tips provided in the published procedure, the experiment should go well for you. However, if your Grignard reaction is slow to start, the most effective aid for starting it is to gently grind the magnesium pieces while they are inside the reaction apparatus, keeping them submerged in the ether and bromobenzene solution. To do this, momentarily open the reaction vial and grind the magnesium with an oven-dried glass stirring rod. BE CAREFUL to not break the stirring rod in your hand. If you do engage in crushing your magnesium once it is in the reaction flask with the ether and bromobenzene, a sign that the Grignard reaction is starting is the appearance of bubbles near the Mg surface. The formation of the Grignard reagent is an exothermic reaction and will boil the ether as the reaction proceeds. Whether the Grignard reaction starts on its own or with coaxing (such as grinding with the stirring rod), the formation of bubbles from spontaneous boiling of the ether is a good sign. If the volume of the reaction mixture decreases during the formation of the Grignard reagent (by evaporation of ether during the heating/refluxing of the mixture), add additional anhydrous ether to replace the quantity lost, keeping the reaction volume no lower than the 1 mL mark on the reaction vial. If your Grignard reaction develops a white precipitate near the beginning this is a bad sign, indicating moisture may have been introduced somehow. A grayish green or brown mixture (with little or no precipitate) is the desired appearance of the Grignard reaction. If the white precipitate is substantial it may be necessary to start the experiment over. Dry ice will be provided near the Organic Dispensing Hood. There will probably be a mallet of some sort and a cloth bag for crushing the dry ice. At the time when you need the dry ice (not before), quickly measure roughly one gram of CO2, place it inside the cloth, and crush it with the mallet. Use the resulting powder for the reaction. Take care handling the dry ice needed for reaction with the phenylmagnesium bromide. Contact with the skin can result in tissue damage. Minimize the time the dry ice is exposed to the air after crushing and before adding the Grignard reagent, since it will rapidly condense moisture on its surface. The first place to stop during the reaction is after the hydrolysis step in the middle of page 275. If you take a break here, DO NOT store your product in a conical reaction vial (we need to clean these and turn them around for use by other students). Place your hydrolysis mixture in an ordinary 5-mL screw cap vial and label it for storage. The vial does not have to be dry for storage (since you've just added an aqueous solution for the hydrolysis step). Once you have the crude product, recrystallize it using a Craig tube, as directed in the text. Interpret the IR spectrum for benzoic acid shown on page 276. You will not run your own IR spectrum. grignd97.doc ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From bowersmy@plu.edu Sat Apr 26 20:19:50 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA20476 for ; Sat, 26 Apr 1997 20:19:49 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II69R8WXMO008D45@plu.edu> for organic1@rainier.chem.plu.edu; Sat, 26 Apr 1997 20:16:01 PDT Date: Sat, 26 Apr 1997 20:16:01 -0700 (PDT) From: bowersmy@plu.edu Subject: hydroboration To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I read the study guide, but I am wondering if we are going to be held responsible for know the mechanism of hydroboration-oxidation, or if we just have to know about it. From steelecl@plu.edu Sun Apr 27 17:37:08 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id RAA26887 for ; Sun, 27 Apr 1997 17:37:08 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II7IDXC800007RJR@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 27 Apr 1997 17:33:23 PDT Date: Sun, 27 Apr 1997 17:33:23 -0700 (PDT) From: steelecl@plu.edu To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Can someone explain what the difference is between spin-spin coupling and signal splitting. On pg. 562 of the book, I do not understand what is meant by "spin-spin coupling occurs between sets of protons that have the same chemical shift" but "spin-spin coupling leads to signal splitting only when the sets of protons have different chemical shifts." Caroline From steelecl@plu.edu Sun Apr 27 17:37:39 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id RAA26892 for ; Sun, 27 Apr 1997 17:37:38 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II7IEI7J3A007RJR@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 27 Apr 1997 17:33:51 PDT Date: Sun, 27 Apr 1997 17:33:50 -0700 (PDT) From: steelecl@plu.edu To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Can someone explain the reciprocity of coupling constants? Caroline From LStandifer@msn.com Sun Apr 27 19:48:24 1997 Received: from UPSMOT07 ([204.95.110.91]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id TAA27544 for ; Sun, 27 Apr 1997 19:48:23 -0700 Received: from upmajb09 - 204.95.110.82 by email.msn.com with Microsoft SMTPSVC; Sun, 27 Apr 1997 19:41:31 -0700 Date: Sun, 27 Apr 97 21:09:01 UT From: "LeRoy Standifer" Message-Id: To: organic1 Subject: TOJC Chapter 9 Question about energies of activation, Chapter 9: On page 381 are a few chain initiation and chain propagation steps and their respective energies of activation and delta-H's. I know how to calculate delta-H, but where did these values for the energies of activation come from? Are they on a table somewhere other than in the book, or was there a formula in the textbook that I overlooked? The book says the energy of activation must be calculated rather than directly measured; I perused the text and did not find a formula. Ideas? C. Krancich From sounthna@plu.edu Sun Apr 27 20:19:16 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA27773 for ; Sun, 27 Apr 1997 20:19:16 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II7O1TRD9S008RJZ@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 27 Apr 1997 20:15:25 PDT Date: Sun, 27 Apr 1997 20:15:25 -0700 (PDT) From: sounthna@plu.edu Subject: learning group problem 9 To: Questions!!! Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII For problem 1b of the learning trans-1,2-dimethylcyclohexane reacts with Cl2. Couldnt the radical Cl react with any of the hydrogens on the ring or the methyl hydrogens, since Cl isn't selective like Br2 is? Does the stability of the radical alkyl affect which hydrogen will be attacked? From boothcj@plu.edu Sun Apr 27 20:19:17 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA27777 for ; Sun, 27 Apr 1997 20:19:16 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II7O1Y0XS0008E4E@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 27 Apr 1997 20:15:31 PDT Date: Sun, 27 Apr 1997 20:15:31 -0700 (PDT) From: boothcj@plu.edu To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII In the chpt 9 LG probs., for #2, how would I be able to make ethane into ethene? What reagents would i need to add to make this happen? From boothcj@plu.edu Sun Apr 27 20:52:16 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA27995 for ; Sun, 27 Apr 1997 20:52:16 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II7P6RXYK0008BSS@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 27 Apr 1997 20:48:27 PDT Date: Sun, 27 Apr 1997 20:48:26 -0700 (PDT) From: boothcj@plu.edu Subject: formal lab report To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII For the acetylsalicylic lab, what would i call the apparattus used to test for the melting point? And do we have to also describe the test for purity. From bobbtl@plu.edu Sun Apr 27 21:33:25 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA28871 for ; Sun, 27 Apr 1997 21:33:23 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II7QLYTEQ8007VZH@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 27 Apr 1997 21:28:59 PDT Date: Sun, 27 Apr 1997 21:28:58 -0700 (PDT) From: bobbtl@plu.edu Subject: Problem 9.5 To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The book says that chloroethane could be formed by the combination of two methyl radicals that then reacts with chlorine in a substitution reaction. Could chloroethane also be formed if a molecule of methyl chloride had a H removed by a chlorine atom (similar to step 2) and this methyl chloride radical would react with a methyl radical? From petershm@plu.edu Sun Apr 27 21:41:53 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA28920 for ; Sun, 27 Apr 1997 21:41:52 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II7QX05JWW007XJQ@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 27 Apr 1997 21:37:54 PDT Date: Sun, 27 Apr 1997 21:37:50 -0700 (PDT) From: petershm@plu.edu Subject: Re: Problem 9.5 In-reply-to: To: bobbtl@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I was wondering if you knew how many references we needed for our formal report? Is the Pavia and our text book enough, and if not what kind of books should we get? Thanks, HP From fryhle@u.washington.edu Sun Apr 27 21:49:51 1997 Received: from jason01.u.washington.edu (jason01.u.washington.edu [140.142.70.24]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA28998 for ; Sun, 27 Apr 1997 21:49:50 -0700 Received: from homer01.u.washington.edu (homer01.u.washington.edu [140.142.70.11]) by jason01.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id VAA16902; Sun, 27 Apr 1997 21:46:06 -0700 Received: from localhost (fryhle@localhost) by homer01.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id VAA25954; Sun, 27 Apr 1997 21:46:06 -0700 Date: Sun, 27 Apr 1997 21:46:06 -0700 (PDT) From: Craig Fryhle To: bowersmy@plu.edu cc: organic1 Subject: Re: hydroboration In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Michelle, et al, You should know the mechanism for the hydroboration step, since it shows why the stereochemistry of the hydroboration step is syn. You don't need to know the mechanism for the oxidation step, except that the boron is replaced by OH with retention of configuration. So, the net process is syn addition of H and OH (i.e. H2O), and it is anti-markovnikov. CBF On Sat, 26 Apr 1997 bowersmy@plu.edu wrote: > I read the study guide, but I am wondering if we are going to be held > responsible for know the mechanism of hydroboration-oxidation, or if we > just have to know about it. > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From fryhle@u.washington.edu Sun Apr 27 21:51:54 1997 Received: from jason05.u.washington.edu (jason05.u.washington.edu [140.142.78.6]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA29029 for ; Sun, 27 Apr 1997 21:51:53 -0700 Received: from homer01.u.washington.edu (homer01.u.washington.edu [140.142.70.11]) by jason05.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id VAA16198; Sun, 27 Apr 1997 21:48:10 -0700 Received: from localhost (fryhle@localhost) by homer01.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id VAA18044; Sun, 27 Apr 1997 21:48:09 -0700 Date: Sun, 27 Apr 1997 21:48:09 -0700 (PDT) From: Craig Fryhle To: boothcj@plu.edu cc: organic1 Subject: Re: formal lab report In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII The apparatus used to measure melting points is called Melt-Temp (brand name). And yes, you should discuss the test for purity. CBF On Sun, 27 Apr 1997 boothcj@plu.edu wrote: > For the acetylsalicylic lab, what would i call the apparattus used to test > for the melting point? And do we have to also describe the test for > purity. > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From crouthmr@plu.edu Sun Apr 27 21:59:22 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA29098 for ; Sun, 27 Apr 1997 21:59:21 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II7RIPIKTW0088X1@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 27 Apr 1997 21:55:21 PDT Date: Sun, 27 Apr 1997 21:55:20 -0700 (PDT) From: Sourcrout Subject: Informal request for those Formal Reports To: Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Excuse me. I'm attempting to compile a class average for my results for the formal report and do need some results to calculate the average as one might expect. I would greatly appreciate your support if you could email meyour results for lab 1 conducted April 7-April 14. I needthe following information: mols (or grams) of 4-methylcyclohexanol mols (or grams) of 4-methylcylcohxene BP determined during distillation % yield I know this is a lot to ask, but you are all such nice guys and gals, and I know you're all into spreading the love. So you can send me all or some (hopefully not none) of these results for your lab 15. Thanks all. Love, MC From balaislv@plu.edu Mon Apr 28 09:31:08 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id JAA03384 for ; Mon, 28 Apr 1997 09:31:07 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II8FOIMC800083GK@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 28 Apr 1997 09:27:14 PDT Date: Mon, 28 Apr 1997 09:27:12 -0700 (PDT) From: "L.B." Subject: Re: Problem 9.5 In-reply-to: To: petershm@plu.edu Cc: bobbtl@plu.edu, organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII You should definitely use Solomon's and Pavia's. You need to list any references that will help you in writing the paper. The library is always a big help. And it doesn't matter how many you have as long as you have some. The more the merrier, I think. Leilani *~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~* ~ ~ * Pacific Lutheran University * ~ E-mail Address: balaislv@plu.edu ~ * (206) 535-7718 * ~ ~ *~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~* On Sun, 27 Apr 1997 petershm@plu.edu wrote: > I was wondering if you knew how many references we needed for our formal > report? Is the Pavia and our text book enough, and if not what kind of > books should we get? Thanks, HP > > From callahnl@plu.edu Mon Apr 28 11:38:14 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id LAA04187 for ; Mon, 28 Apr 1997 11:38:13 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II8K4O6TUO007ZRM@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 28 Apr 1997 11:34:06 PDT Date: Mon, 28 Apr 1997 11:34:02 -0700 (PDT) From: "D'oh" Subject: Re: learning group problem 9 In-reply-to: To: sounthna@plu.edu Cc: Questions!!! Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII hey Southna, Cl would react with any of the hydrogen atoms on the ring or methyl groups. The selectivity is nearly random, and cannot be really predicted. If you look at pages 387 and 388, you can see that sometimes the Cl reacts predominately with the more stable carbon radical, and other times it doesn't. I think the most important thing to note is that you will get a mixture of all monochlorinated possibilities, and then a load of ploychlorinated compounds which are not really worth mentioning except that they exist. -nick On Sun, 27 Apr 1997 sounthna@plu.edu wrote: > For problem 1b of the learning trans-1,2-dimethylcyclohexane reacts with > Cl2. Couldnt the radical Cl react with any of the hydrogens on the ring > or the methyl hydrogens, since Cl isn't selective like Br2 is? Does the > stability of the radical alkyl affect which hydrogen will be attacked? > > From kamperka@plu.edu Mon Apr 28 17:19:58 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id RAA06076 for ; Mon, 28 Apr 1997 17:19:57 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II8NSF544W008FCG@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 28 Apr 1997 13:19:30 PDT Date: Mon, 28 Apr 1997 13:19:26 -0700 (PDT) From: kamperka@plu.edu Subject: Re: hydroboration In-reply-to: To: bowersmy@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII It seemed to me from what he said in class today is that we need to know the first part, the hydroboration mechanism, but not the second part, the oxidation part. -KK On Sat, 26 Apr 1997 bowersmy@plu.edu wrote: > I read the study guide, but I am wondering if we are going to be held > responsible for know the mechanism of hydroboration-oxidation, or if we > just have to know about it. > > From kamperka@plu.edu Mon Apr 28 17:19:59 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id RAA06080 for ; Mon, 28 Apr 1997 17:19:58 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II8NYZ6WBC008FCG@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 28 Apr 1997 13:24:53 PDT Date: Mon, 28 Apr 1997 13:24:45 -0700 (PDT) From: kamperka@plu.edu In-reply-to: To: petershm@plu.edu Cc: bobbtl@plu.edu, organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII When our group asked, he said it might be necessary to look at some of the advanced organic textbooks in the library if we had questions, but if we didn't need to use them then just Pavia and our text book were enough. On Sun, 27 Apr 1997 petershm@plu.edu wrote: > I was wondering if you knew how many references we needed for our formal > report? Is the Pavia and our text book enough, and if not what kind of > books should we get? Thanks, HP > > From vogega@plu.edu Mon Apr 28 17:30:58 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id RAA06185 for ; Mon, 28 Apr 1997 17:30:58 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II8WFRKAMS008D2V@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 28 Apr 1997 17:26:31 PDT Date: Mon, 28 Apr 1997 17:26:31 -0700 (PDT) From: vogega@plu.edu Subject: carvone lab To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII group 16- i believe you are also doing the formal lab report on carvone. i have a question for the person that is writing the results and discussion section. what are you writing about for the discussion part. i have a lot of tables i am going to include. there really isn't much to discuss. are results were what was expected. the experiment was mainly just to compare results with ones that were given. if you could provide with any insights as to how to go about this section, please do so. thank you, gretchen From maschhjt@plu.edu Mon Apr 28 18:37:50 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id SAA07654 for ; Mon, 28 Apr 1997 18:37:49 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II8YSBNYEY008O9Y@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 28 Apr 1997 18:33:55 PDT Date: Mon, 28 Apr 1997 18:33:55 -0700 (PDT) From: maschhjt@plu.edu Subject: Grignard lab To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I was wondering do we turn in both a sample of our benzoic acid and the purified benzoic acid crystals, or just the crystals? And if we are supposed to turn in both, what do we do if we have less than 0.08g of benzoic acid to crystalize? Justin From williasl@plu.edu Mon Apr 28 22:24:49 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA08786 for ; Mon, 28 Apr 1997 22:24:48 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II96PETE2O0095DA@plu.edu> for ORGANIC1@RAINIER.CHEM.PLU.EDU; Mon, 28 Apr 1997 22:20:40 PDT Date: Mon, 28 Apr 1997 22:20:39 -0700 (PDT) From: williasl@plu.edu Subject: chain propagation To: THE ORGANIC CHEMLIST Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I was wondering why in the chlorination of methane, why the second reactive chlorine atom produced from the chain initiation step does not become attacked by a methyl radical in the third step of a chain propagation instead of a chlorine atom from a chlorine molecule, or would this be considered a chain termination step? If it is a chain termination step, what would favor the chain propigating step over this step? Can anyone explain this? Thank you. From davidsct@plu.edu Mon Apr 28 23:37:25 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id XAA09182 for ; Mon, 28 Apr 1997 23:37:24 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II9987GHWW008Q1B@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 28 Apr 1997 23:33:11 PDT Date: Mon, 28 Apr 1997 23:33:04 -0700 (PDT) From: davidsct@plu.edu Subject: Re: learning group problem 9 In-reply-to: To: "D'oh" Cc: sounthna@plu.edu, Questions!!! Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII One more note Southna, Yes, I too agree that Cl would react with any of the hydrogen atoms on the ring or methyl groups, however there is evidence in other reactions that shows the %yielded of certain more less stable compounds are formed, vs. the desired stable compound. The number of available sites on less stable radicals is greater than the possible number of sites on the more stable radicals, therefore there is a higher % of less stable compounds formed vs. the more stable one. Available sites can be defined as anywhere there is a Hydrogen that can be removed. And in Ch3, primary, and secondary connected compounds there are obviously more hydrogens available for removal, vs. that of a tertiary. cd. On Mon, 28 Apr 1997, D'oh wrote: > > hey Southna, > > Cl would react with any of the hydrogen atoms on the ring or > methyl groups. The selectivity is nearly random, and cannot be really > predicted. If you look at pages 387 and 388, you can see that sometimes > the Cl reacts predominately with the more stable carbon radical, and other > times it doesn't. I think the most important thing to note is that you > will get a mixture of all monochlorinated possibilities, and then a load > of ploychlorinated compounds which are not really worth mentioning except > that they exist. > > -nick > > > > > On Sun, 27 Apr 1997 sounthna@plu.edu wrote: > > > For problem 1b of the learning trans-1,2-dimethylcyclohexane reacts with > > Cl2. Couldnt the radical Cl react with any of the hydrogens on the ring > > or the methyl hydrogens, since Cl isn't selective like Br2 is? Does the > > stability of the radical alkyl affect which hydrogen will be attacked? > > > > > > From harriscr@plu.edu Tue Apr 29 01:29:42 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id BAA10067 for ; Tue, 29 Apr 1997 01:29:42 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II9D62GZYO0087LE@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 29 Apr 1997 01:25:51 PDT Date: Tue, 29 Apr 1997 01:25:51 -0700 (PDT) From: harriscr@plu.edu Subject: Compound Names To: Organic chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Hi, We are having lots of trouble finding information about bromohydrin, lactone, etc. for our formal report. Could you please give us some hints to where we could find this info. without too much trouble. Thanks, Group #11 From harriscr@plu.edu Tue Apr 29 01:31:19 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id BAA10120 for ; Tue, 29 Apr 1997 01:31:18 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II9D7HRLP20087LE@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 29 Apr 1997 01:27:00 PDT Date: Tue, 29 Apr 1997 01:27:00 -0700 (PDT) From: harriscr@plu.edu Subject: formal lab To: Organic chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Do we turn in the formal lab in the box located in the open lab? -Clayton From callahnl@plu.edu Tue Apr 29 09:10:07 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id JAA12373 for ; Tue, 29 Apr 1997 09:10:07 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II9T8PIK4G008O1K@plu.edu> for ORGANIC1@rainier.chem.plu.edu; Tue, 29 Apr 1997 09:06:08 PDT Date: Tue, 29 Apr 1997 09:06:07 -0700 (PDT) From: "D'oh" Subject: Re: chain propagation In-reply-to: To: williasl@plu.edu Cc: THE ORGANIC CHEMLIST Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII hey Williasl, It would be a chain terminating step for the methyl radical to bond to the chlorine radical. The reason that it doesn't do this, or rather doesn't do it all that often, is because chlorine radicals never really exist in large amounts. This means that the more common reaction would be for a methyl radical the find a Cl2 and react with that instead. However, even though the terminating step above isn't common, it still does occur enough to stop the reaction. -nick On Mon, 28 Apr 1997 williasl@plu.edu wrote: > > I was wondering why in the chlorination of methane, why the second > reactive chlorine atom produced from the chain initiation step does not > become attacked by a methyl radical in the third step of a chain > propagation instead of a chlorine atom from a chlorine molecule, or would > this be considered a chain termination step? If it is a chain termination > step, what would favor the chain propigating step over this step? > Can anyone explain this? Thank you. > > From blackkl@plu.edu Tue Apr 29 09:21:21 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id JAA12499 for ; Tue, 29 Apr 1997 09:21:20 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01II9TMO97FK00909P@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 29 Apr 1997 09:17:24 PDT Date: Tue, 29 Apr 1997 09:17:22 -0700 (PDT) From: blackkl@plu.edu Subject: Re: Informal request for those Formal Reports In-reply-to: To: Sourcrout Cc: Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Here are my results from the lab #15..hope it helps. grams of 4-methylcyclohexanol 1.57g grams of 4-methylcyclohexene .45g the boiling point that I reached was 103 C The % yield was 34.1% On Sun, 27 Apr 1997, Sourcrout wrote: > Excuse me. > I'm attempting to compile a class average for my results for the formal > report and do need some results to calculate the average as one might > expect. I would greatly appreciate your support if you could email meyour > results for lab 1 conducted April 7-April 14. I needthe following > information: > > mols (or grams) of 4-methylcyclohexanol > mols (or grams) of 4-methylcylcohxene > BP determined during distillation > % yield > > I know this is a lot to ask, but you are all such nice guys and gals, and > I know you're all into spreading the love. So you can send me all or some > (hopefully not none) of these results for your lab 15. > > Thanks all. > Love, > MC > > From LStandifer@msn.com Tue Apr 29 11:42:05 1997 Received: from upsmot03.msn.com (upsmot03.msn.com [204.95.110.85]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id LAA13215 for ; Tue, 29 Apr 1997 11:42:04 -0700 Received: from upmajb02.msn.com (upmajb02.msn.com [204.95.110.74]) by upsmot03.msn.com (8.6.8.1/Configuration 4) with SMTP id LAA04957 for ; Tue, 29 Apr 1997 11:33:10 -0700 Date: Tue, 29 Apr 97 18:40:34 UT From: "LeRoy Standifer" Message-Id: To: organic1 Subject: TOJC Chapter 9 To Williasl, In the chlorination of methane, there are three possible chain terminating steps: i. CH3 * + Cl * -----------> CH3Cl ii. Cl * + Cl * -----------> Cl2 iii. CH3 * + CH3 * -------> CH3CH3 That doesn't mean, though, that these steps occur at the same rate. The concentration of each of these critters, and their respective energies of activations and delta-H will affect the rate at which these steps occur. C. Krancich From fryhle@u.washington.edu Tue Apr 29 12:57:51 1997 Received: from jason02.u.washington.edu (jason02.u.washington.edu [140.142.76.8]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id MAA13611 for ; Tue, 29 Apr 1997 12:57:50 -0700 Received: from homer06.u.washington.edu (homer06.u.washington.edu [140.142.76.13]) by jason02.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id MAA11430; Tue, 29 Apr 1997 12:54:04 -0700 Received: from localhost (fryhle@localhost) by homer06.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id MAA73652; Tue, 29 Apr 1997 12:54:03 -0700 Date: Tue, 29 Apr 1997 12:54:03 -0700 (PDT) From: Craig Fryhle To: maschhjt@plu.edu cc: organic1 Subject: Re: Grignard lab In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII I would suggest determining the weight of your crude product (as a matter of habit) and saving at least a small sample of your crude benzoic acid product before recrystallization. That way, if the recrystallization doesn't go well, you will still have at least some sample to turn in. I routinely save a portion of a crude product for purposes of comparison of crude and purified samples. As for you folks in the class, I would turn in both the remaining crude and the purified sample, in vials labeled separately and taped together afterward. If the yield of crude product is low, you can try to scale back the recrystallization, or opt to take the results of turning in only a crude product with its respective purity and mp. CBF On Mon, 28 Apr 1997 maschhjt@plu.edu wrote: > > I was wondering do we turn in both a sample of our benzoic acid and the > purified benzoic acid crystals, or just the crystals? And if we are > supposed to turn in both, what do we do if we have less than 0.08g of > benzoic acid to crystalize? > > Justin > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From balaislv@plu.edu Tue Apr 29 12:57:59 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id MAA13638 for ; Tue, 29 Apr 1997 12:57:58 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIA178I3TA009N76@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 29 Apr 1997 12:54:03 PDT Date: Tue, 29 Apr 1997 12:53:59 -0700 (PDT) From: "L.B." Subject: Re: formal lab In-reply-to: To: harriscr@plu.edu Cc: Organic chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII You need to turn the report into the lab box just like any other lab report. Leilani *~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~* ~ ~ * Pacific Lutheran University * ~ E-mail Address: balaislv@plu.edu ~ * (206) 535-7718 * ~ ~ *~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~* On Tue, 29 Apr 1997 harriscr@plu.edu wrote: > > > Do we turn in the formal lab in the box located in the open lab? > > -Clayton > > From fryhle@u.washington.edu Tue Apr 29 12:59:43 1997 Received: from jason01.u.washington.edu (jason01.u.washington.edu [140.142.70.24]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id MAA13673 for ; Tue, 29 Apr 1997 12:59:42 -0700 Received: from homer06.u.washington.edu (homer06.u.washington.edu [140.142.76.13]) by jason01.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id MAA13280; Tue, 29 Apr 1997 12:55:56 -0700 Received: from localhost (fryhle@localhost) by homer06.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id MAA34864; Tue, 29 Apr 1997 12:55:56 -0700 Date: Tue, 29 Apr 1997 12:55:56 -0700 (PDT) From: Craig Fryhle To: harriscr@plu.edu cc: Organic chemistry Subject: Re: formal lab In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Turn your formal lab reports in to the box in the Open Lab. CBF On Tue, 29 Apr 1997 harriscr@plu.edu wrote: > > > Do we turn in the formal lab in the box located in the open lab? > > -Clayton > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From raquetce@plu.edu Tue Apr 29 13:36:16 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id NAA13966 for ; Tue, 29 Apr 1997 13:36:15 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIA2ISARCG0095QQ@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 29 Apr 1997 13:31:34 PDT Date: Tue, 29 Apr 1997 13:31:33 -0700 (PDT) From: raquetce@plu.edu Subject: chapter 10 To: org chem list Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII On page 416 in Chapter 10 there is an example of a phenol called p-Mehylphenol. I am not quite sure where the p comes in in naming it. Can someone explain it to me? Thanks. From callahnl@plu.edu Tue Apr 29 14:36:50 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id OAA14330 for ; Tue, 29 Apr 1997 14:36:49 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIA4NNKBQO009A2K@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 29 Apr 1997 14:32:47 PDT Date: Tue, 29 Apr 1997 14:32:45 -0700 (PDT) From: "D'oh" Subject: Re: chapter 10 In-reply-to: To: raquetce@plu.edu Cc: org chem list Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII hey raquetce, p- stands for para. It was an older style of naming, and I'm not sure how common it is anymore. It means the methyl group is attached to the 4 carbon of the ring. The other two parts two this naming system are ortho and meta, meaning 2nd and 3rd carbon respectively. -nick On Tue, 29 Apr 1997 raquetce@plu.edu wrote: > > On page 416 in Chapter 10 there is an example of a phenol called > p-Mehylphenol. I am not quite sure where the p comes in in naming > it. Can someone explain it to me? Thanks. > > From davidsct@plu.edu Tue Apr 29 15:50:02 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id PAA19097 for ; Tue, 29 Apr 1997 15:50:01 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIA77RGH80009UM0@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 29 Apr 1997 15:46:14 PDT Date: Tue, 29 Apr 1997 15:46:13 -0700 (PDT) From: davidsct@plu.edu Subject: Re: chapter 10 In-reply-to: To: raquetce@plu.edu Cc: org chem list Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I believe the reason the phenol is called p-methylphenol is becuase if you look on page 616, in Ch. 14, when two substituens are present in a benzene, or in this case a phenol, the relative position is indicated by the prefix p for para, and this is becuase the substituents in the phenol on page 416 are on opposite sides, therefore being named with the prefix p, or para. cd On Tue, 29 Apr 1997 raquetce@plu.edu wrote: > > On page 416 in Chapter 10 there is an example of a phenol called > p-Mehylphenol. I am not quite sure where the p comes in in naming > it. Can someone explain it to me? Thanks. > > From kamperka@plu.edu Tue Apr 29 19:01:34 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id TAA20170 for ; Tue, 29 Apr 1997 19:01:33 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIADW414WW009BW3@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 29 Apr 1997 18:57:39 PDT Date: Tue, 29 Apr 1997 18:57:39 -0700 (PDT) From: kamperka@plu.edu Subject: signal splitting To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII So maybe I'm a little bit behind, but could someone please shed a little light on signal splitting and spin-spin coupling (about p. 561 in the text)? It's just not real clear to me. Thanks, -KK From 107744.2473@compuserve.com Tue Apr 29 20:23:21 1997 Received: from hil-img-2.compuserve.com (hil-img-2.compuserve.com [149.174.177.132]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA20625 for ; Tue, 29 Apr 1997 20:23:20 -0700 Received: by hil-img-2.compuserve.com (8.6.10/5.950515) id XAA27963; Tue, 29 Apr 1997 23:19:35 -0400 Date: Tue, 29 Apr 1997 23:18:25 -0400 From: "howard r. kletke" <107744.2473@compuserve.com> Subject: lg 5 To: unknown Message-ID: <199704292319_MC2-15AC-D1AC@compuserve.com> Michael, Today our group met to talk about the formal report. We have planned on meeting again tomorrow, each of us with copies of our rough drafts, in the science building at 3:30 p.m. Please try to have your draft ready. Thanks, Monica From 107744.2473@compuserve.com Tue Apr 29 20:29:37 1997 Received: from arl-img-4.compuserve.com (arl-img-4.compuserve.com [149.174.217.134]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA20681 for ; Tue, 29 Apr 1997 20:29:36 -0700 Received: by arl-img-4.compuserve.com (8.6.10/5.950515) id XAA20212; Tue, 29 Apr 1997 23:25:51 -0400 Date: Tue, 29 Apr 1997 23:24:51 -0400 From: "howard r. kletke" <107744.2473@compuserve.com> Subject: 10.10 To: unknown Message-ID: <199704292324_MC2-15AC-D213@compuserve.com> In this section of the study sheets, it is written that we need to know the reaction conditions for forming tosylates and mesylates. Are the reaction conditions the fact that the reaction takes place in a base and (-HCl)? Thanks, Monica From 107744.2473@compuserve.com Tue Apr 29 20:54:30 1997 Received: from hil-img-4.compuserve.com (hil-img-4.compuserve.com [149.174.177.134]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA20873 for ; Tue, 29 Apr 1997 20:54:29 -0700 Received: by hil-img-4.compuserve.com (8.6.10/5.950515) id XAA14917; Tue, 29 Apr 1997 23:50:43 -0400 Date: Tue, 29 Apr 1997 23:42:10 -0400 From: "howard r. kletke" <107744.2473@compuserve.com> Subject: formal reports To: unknown Message-ID: <199704292342_MC2-15AC-D300@compuserve.com> With regard to the reference section of the formal report, is the correct format, for books: Author(s), Title, Publishing company, place where it was published, copyright date, and page numbers? Thanks, Monica From raquetce@plu.edu Tue Apr 29 21:40:16 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA21182 for ; Tue, 29 Apr 1997 21:40:16 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIAJFTV8NK0092U0@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 29 Apr 1997 21:36:19 PDT Date: Tue, 29 Apr 1997 21:36:19 -0700 (PDT) From: raquetce@plu.edu Subject: chapter 10 To: org chem list Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII On page 417 in one of the sample compounds I am not sure why it has the name 1,2-Dimethoxyethane. Can someone explain? Thank you From fryhle@u.washington.edu Tue Apr 29 21:46:09 1997 Received: from jason01.u.washington.edu (jason01.u.washington.edu [140.142.70.24]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id VAA21281 for ; Tue, 29 Apr 1997 21:46:08 -0700 Received: from homer10.u.washington.edu (homer10.u.washington.edu [140.142.78.11]) by jason01.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with ESMTP id VAA13100; Tue, 29 Apr 1997 21:42:23 -0700 Received: from localhost (fryhle@localhost) by homer10.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.03) with SMTP id VAA97110; Tue, 29 Apr 1997 21:42:23 -0700 Date: Tue, 29 Apr 1997 21:42:23 -0700 (PDT) From: Craig Fryhle To: "howard r. kletke" <107744.2473@compuserve.com> cc: unknown Subject: Re: formal reports In-Reply-To: <199704292342_MC2-15AC-D300@compuserve.com> Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Examples of reference formats for books and journals are provided with the sample paper given as a model for the formal report. (In the handout I mentioned specific reference numbers in the sample paper that pertain to each type of document.) I hope that helps. CBF On Tue, 29 Apr 1997, howard r. kletke wrote: > With regard to the reference section of the formal report, is the > correct format, for books: Author(s), Title, Publishing company, place > where it was published, copyright date, and page numbers? > Thanks, Monica > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From youngcf@plu.edu Wed Apr 30 10:29:24 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id KAA25667 for ; Wed, 30 Apr 1997 10:29:24 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIBAB9MOM8009ZLC@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 30 Apr 1997 10:25:21 PDT Date: Wed, 30 Apr 1997 10:25:21 -0700 (PDT) From: youngcf@plu.edu Subject: Formal lab reports. To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII To all: Group 4 is doing the formal lab report in regards to the essential oils experiment (eugenol). If possible, could everyone post there percent yields and there boiling points for this experiment. I need it to graph. I know it is a little late to ask for, but I just thought of the idea. If you don't want to post the information to the list, then please call me and leave a message at my extention. X7950 Thanks Curtis F. Young From hiattzr@plu.edu Wed Apr 30 11:04:07 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id LAA25872 for ; Wed, 30 Apr 1997 11:04:03 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIBBHE407K00A0DS@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 30 Apr 1997 10:59:24 PDT Date: Wed, 30 Apr 1997 10:59:20 -0700 (PDT) From: hiattzr@plu.edu Subject: Re: chapter 10 In-reply-to: To: raquetce@plu.edu Cc: org chem list Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII To raquetce, The sample compound is named using IUPAC substitutive nomenclature. In this case, the parent chain is the ethane made of of the two CH2's in the middle of the molecule. At each CH2, a methoxy group (CH3-O-) has been substituted for a hydrogen, thus the name 1,2-Di"methoxy"ethane, just like if a Cl was substituted for a hydrogen at each Carbon of the ethane parent chain the compound would be called 1,2-Di"chloro"ethane. In general, R-O- groups are called alkoxy groups. I hope this helps. Zach On Tue, 29 Apr 1997 raquetce@plu.edu wrote: > On page 417 in one of the sample compounds I am not sure why it > has the name 1,2-Dimethoxyethane. Can someone explain? Thank you > > From hodgedb@plu.edu Wed Apr 30 11:27:42 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id LAA26084 for ; Wed, 30 Apr 1997 11:27:41 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIBCCLVUGG00AAMU@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 30 Apr 1997 11:23:50 PDT Date: Wed, 30 Apr 1997 11:23:43 -0700 (PDT) From: hodgedb@plu.edu Subject: Re: Formal lab reports. In-reply-to: To: youngcf@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Group 4, In regard to the essential oil lab that you are doing your formal report on, I recieved a yield of 9%, and a high boiling point of 250 C. I hope that this helps. Dani On Wed, 30 Apr 1997 youngcf@plu.edu wrote: > > To all: > > Group 4 is doing the formal lab report in regards to the essential > oils experiment (eugenol). If possible, could everyone post there percent > yields and there boiling points for this experiment. I need it to graph. > I know it is a little late to ask for, but I just thought of the idea. > If you don't want to post the information to the list, then please call me > and leave a message at my extention. X7950 > > Thanks > > Curtis F. Young > > > > From larsenak@plu.edu Wed Apr 30 11:28:41 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id LAA26109 for ; Wed, 30 Apr 1997 11:28:40 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIBCDVIQJK00ACVM@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 30 Apr 1997 11:24:52 PDT Date: Wed, 30 Apr 1997 11:24:45 -0700 (PDT) From: larsenak@plu.edu Subject: Re: Informal request for those Formal Reports In-reply-to: To: Sourcrout Cc: Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Here are my results from the methylcyclohexene lab. Grams of 4-methylcyclohexanol: .9g moles: .007881 mol " " 4-methylcyclohexene: .3g percentage yield: 40% Boiling point: 101 C On Sun, 27 Apr 1997, Sourcrout wrote: > Excuse me. > I'm attempting to compile a class average for my results for the formal > report and do need some results to calculate the average as one might > expect. I would greatly appreciate your support if you could email meyour > results for lab 1 conducted April 7-April 14. I needthe following > information: > > mols (or grams) of 4-methylcyclohexanol > mols (or grams) of 4-methylcylcohxene > BP determined during distillation > % yield > > I know this is a lot to ask, but you are all such nice guys and gals, and > I know you're all into spreading the love. So you can send me all or some > (hopefully not none) of these results for your lab 15. > > Thanks all. > Love, > MC > > From hodgedb@plu.edu Wed Apr 30 11:37:05 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id LAA26182 for ; Wed, 30 Apr 1997 11:37:04 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIBCNSK7PK00AAMU@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 30 Apr 1997 11:32:51 PDT Date: Wed, 30 Apr 1997 11:32:44 -0700 (PDT) From: hodgedb@plu.edu Subject: Re: Informal request for those Formal Reports In-reply-to: To: Sourcrout Cc: Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Hello, Here are my results from lab 15 (Dehydration of 4-methylcyclohexanol): 1.37 grams 4-methylcyclohexanol ..65 grams 4-methylcyclohexene BP: 100 C 56% yield of 4-methylcyclohexene I hope that this helps you out! DBH On Sun, 27 Apr 1997, Sourcrout wrote: > Excuse me. > I'm attempting to compile a class average for my results for the formal > report and do need some results to calculate the average as one might > expect. I would greatly appreciate your support if you could email meyour > results for lab 1 conducted April 7-April 14. I needthe following > information: > > mols (or grams) of 4-methylcyclohexanol > mols (or grams) of 4-methylcylcohxene > BP determined during distillation > % yield > > I know this is a lot to ask, but you are all such nice guys and gals, and > I know you're all into spreading the love. So you can send me all or some > (hopefully not none) of these results for your lab 15. > > Thanks all. > Love, > MC > > From maschhjt@plu.edu Wed Apr 30 14:15:39 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id OAA27101 for ; Wed, 30 Apr 1997 14:15:38 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIBI7GXDQE00A2QX@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 30 Apr 1997 14:11:22 PDT Date: Wed, 30 Apr 1997 14:11:21 -0700 (PDT) From: maschhjt@plu.edu Subject: Re: Formal lab reports. In-reply-to: To: organic1 , youngcf@plu.edu Reply-to: maschhjt@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Curtis MY percent yield was 11%, and my bp was a high of 250 degrees C. Good luck with your write-up! justin On Wed, 30 Apr 1997 youngcf@plu.edu wrote: > > To all: > > Group 4 is doing the formal lab report in regards to the essential > oils experiment (eugenol). If possible, could everyone post there percent > yields and there boiling points for this experiment. I need it to graph. > I know it is a little late to ask for, but I just thought of the idea. > If you don't want to post the information to the list, then please call me > and leave a message at my extention. X7950 > > Thanks > > Curtis F. Young > > > > From maschhjt@plu.edu Wed Apr 30 14:20:09 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id OAA27163 for ; Wed, 30 Apr 1997 14:20:08 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIBID6UZFY00A2QX@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 30 Apr 1997 14:15:59 PDT Date: Wed, 30 Apr 1997 14:15:57 -0700 (PDT) From: maschhjt@plu.edu Subject: results To: crouthmr , organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Here are my results for the 4-methylcyclohexene lab: 1.04 g of 4-methlycycolohexanol ..22 g of methylcyclohexene a bp of 101 degrees and a % yield of 25% Hope this helps and good luck! Justin From weinmadj@plu.edu Wed Apr 30 19:51:09 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id TAA29393 for ; Wed, 30 Apr 1997 19:51:08 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIBTVEG7Z400A4DZ@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 30 Apr 1997 19:46:00 PDT Date: Wed, 30 Apr 1997 19:45:59 -0700 (PDT) From: weinmadj@plu.edu Subject: references To: fryhle@u.washington.edu, organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I have a few references from the internet and I was wondering if anyone knew how do cite them. One example is I got an article from Encyclopedia Britanica Online and I don't know how to cite it. Could anyone help? David From sounthna@plu.edu Wed Apr 30 20:22:05 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA29569 for ; Wed, 30 Apr 1997 20:22:04 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIBV0EANPC009JLS@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 30 Apr 1997 20:18:16 PDT Date: Wed, 30 Apr 1997 20:18:16 -0700 (PDT) From: sounthna@plu.edu Subject: Learning Group Chapter 10!!! To: Questions!!! Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Hey class...on what day are the learning groups for chapter 10 going? Nope From blackkl@plu.edu Wed Apr 30 20:38:04 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA29673 for ; Wed, 30 Apr 1997 20:38:03 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIBVJQFG0C00ALGC@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 30 Apr 1997 20:33:58 PDT Date: Wed, 30 Apr 1997 20:33:52 -0700 (PDT) From: blackkl@plu.edu Subject: Re: references In-reply-to: To: weinmadj@plu.edu Cc: fryhle@u.washington.edu, organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I hope this helps, we learned how to do it in our writing class. First you list it like you would list a normal article with the author of the article and then the year of publication or the issue along with the month of that issue. The title of the article and then the source of where it came from..then identify it as an electronic source like on line and provide a path or electronic address for the source so that a researcher can find it. I hope this helps but if you have any more questions let me know because I have a book that explains it. Good Luck!! On Wed, 30 Apr 1997 weinmadj@plu.edu wrote: > > > I have a few references from the internet and I was wondering if anyone > knew how do cite them. One example is I got an article from Encyclopedia > Britanica Online and I don't know how to cite it. Could anyone help? > > David > > From blackkl@plu.edu Wed Apr 30 20:40:31 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA29713 for ; Wed, 30 Apr 1997 20:40:31 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIBVMH1OY800ALGC@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 30 Apr 1997 20:36:06 PDT Date: Wed, 30 Apr 1997 20:36:04 -0700 (PDT) From: blackkl@plu.edu Subject: Re: Learning Group Chapter 10!!! In-reply-to: To: sounthna@plu.edu Cc: Questions!!! Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I think that they are on Monday, May 5...that is what I am planning on so if anyone knows different please let me know too! Thanks!! On Wed, 30 Apr 1997 sounthna@plu.edu wrote: > > Hey class...on what day are the learning groups for chapter 10 going? > > Nope > > From hendrycl@plu.edu Wed Apr 30 20:47:56 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA29845 for ; Wed, 30 Apr 1997 20:47:55 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIBVVXAH0Y00A6WL@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 30 Apr 1997 20:43:42 PDT Date: Wed, 30 Apr 1997 20:43:42 -0700 (PDT) From: hendrycl@plu.edu Subject: ISIS draw To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Does anyone know how to take reactions drawn in ISIS draw and import them into word? chase From taylormr@plu.edu Wed Apr 30 20:50:38 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA29880 for ; Wed, 30 Apr 1997 20:50:38 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIBW0GHFLS009UAE@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 30 Apr 1997 20:46:36 PDT Date: Wed, 30 Apr 1997 20:46:34 -0700 (PDT) From: "M.Taylor" Subject: Re: Learning Group Chapter 10!!! In-reply-to: To: sounthna@plu.edu Cc: Questions!!! Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Nope, The learning group for chapter 10 is monday morning. Michele On Wed, 30 Apr 1997 sounthna@plu.edu wrote: > > Hey class...on what day are the learning groups for chapter 10 going? > > Nope > > From charbogd@plu.edu Wed Apr 30 23:15:12 1997 Received: from pepper.PLU.edu (pepper.PLU.edu [152.117.1.7]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id XAA00739 for ; Wed, 30 Apr 1997 23:15:12 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIC11NMHO000AJ5C@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 30 Apr 1997 23:11:09 PDT Date: Wed, 30 Apr 1997 23:11:05 -0700 (PDT) From: "Gabriel D. Charbonneau" Subject: Re: ISIS draw In-reply-to: To: hendrycl@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII chase, It's too bad that you already made the drawings, because I know how to create an ISIS draw object from within word. Go to the insert menu, choose object, select ISIS Sketck (or something like that). When you exit ISIS draw it will prompt to update your word document. Maybe you can do this another way, but this works for me. gabe On Wed, 30 Apr 1997 hendrycl@plu.edu wrote: > > Does anyone know how to take reactions drawn in ISIS draw and import them > into word? > > chase > >