From youngcf@plu.edu Thu May 1 10:31:15 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 KAA04799 for ; Thu, 1 May 1997 10:31:14 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IICONOCXQ800AEYS@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 1 May 1997 10:27:02 PDT Date: Thu, 01 May 1997 10:27:02 -0700 (PDT) From: youngcf@plu.edu Subject: Thanks To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII To All: I want to thank those that helped me out by giving me their lab information about the eugenol experiment. It Has helped me greatly. For those who have not, I would appreciate it if you could try to post your info. by later today. Again I would just like the percent recovery of eugenol and the gram(s) of cloves used. Thanks Curtis F. Young From sounthna@plu.edu Thu May 1 12:55:24 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 MAA05556 for ; Thu, 1 May 1997 12:55:23 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IICTOTEHEO00ACX2@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 1 May 1997 12:51:32 PDT Date: Thu, 01 May 1997 12:51:29 -0700 (PDT) From: sounthna@plu.edu 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, I haven't tried imported from ISIS draw but I have don't from other graphics programs. What you do is make or insert a frame in your workd document, copy your ISIS draw and just paste in into the box. If that doesn't work you can always cut and paste. Hope that helps Nope 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 > > From crouthmr@plu.edu Thu May 1 13:43:07 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 NAA05822 for ; Thu, 1 May 1997 13:43:07 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IICVCJ5U1E00AL6E@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 1 May 1997 13:38:51 PDT Date: Thu, 01 May 1997 13:38:50 -0700 (PDT) From: Sourcrout Subject: Formal Report To: Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I am not certain about the grading criteria for the report. Are we supposed to designate the work that each group member did. And if so, how and where. MC From hendrycl@plu.edu Thu May 1 14:11:58 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 OAA06018 for ; Thu, 1 May 1997 14:11:57 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IICUWQ513600ABLJ@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 1 May 1997 13:26:10 PDT Date: Thu, 01 May 1997 13:26:09 -0700 (PDT) From: hendrycl@plu.edu Subject: ISIS draw To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Thanks to Gabe and Nope I've found a great way to stick equations into word. (I use word 7 for windows 95.) In word click "insert" - "object" - select "ISIS/Draw Sketch" (this will switch you into word)- copy your equation - switch back into word and paste. fast as greased lightning. chase From gigraykc@plu.edu Thu May 1 14:17:28 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 OAA06115 for ; Thu, 1 May 1997 14:17:26 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IICWK208LS009WFW@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 1 May 1997 14:13:14 PDT Date: Thu, 01 May 1997 14:13:10 -0700 (PDT) From: gigraykc@plu.edu Subject: Re: Formal Report In-reply-to: To: Sourcrout Cc: Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The grading criteria for the formal reports are contained within the Lab class syllabus. Each individual part is 20% of the grade. The four parts are as follows: Title, Abstract, Registry Numbers, Notation and Format of Reference-20% Introduction-20% Results and Discussion-20% Experimental Section-20% and to obtain a 100% grading scale the final 20% is your individual part added again. The job assignments and person responsible for each section should be typed at the end of the report. All members of the group should sign the report there, too. I hope that clears up everything for you!-Kelli ,. '., CONJUCTION JUCTION!!! ,.`' _______ _______ _______ _______ _l_l___ ! l l ! ! l l ! ! l l ! ! l l ! ! l__!___ ! l l ! ! l l ! ! l l ! ! l l ! ! ___0 -0---0- -0---0- -0---0- -0---0- -0--0------) WHAT'S YOUR FUNCTION!?!?!?! On Thu, 1 May 1997, Sourcrout wrote: > I am not certain about the grading criteria for the report. Are we > supposed to designate the work that each group member did. And if so, how > and where. > MC > > > From larsenak@plu.edu Thu May 1 15:14:35 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 PAA06640 for ; Thu, 1 May 1997 15:14:30 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IICYJZY1AU00A0D5@plu.edu> for Organic1@rainier.chem.plu.edu; Thu, 1 May 1997 15:10:24 PDT Date: Thu, 01 May 1997 15:10:23 -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 On the formal lab report, does the introduction have to be in the past tense and the passive or does it matter? From smithtw@plu.edu Thu May 1 15:22:57 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 PAA06722 for ; Thu, 1 May 1997 15:22:56 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IICYUBR4TS00AS6I@plu.edu> for Organic1@rainier.chem.plu.edu; Thu, 1 May 1997 15:18:44 PDT Date: Thu, 01 May 1997 15:18:42 -0700 (PDT) From: smithtw@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 Doesn't it all have to be in past tense? The whole report? On Thu, 1 May 1997 larsenak@plu.edu wrote: > On the formal lab report, does the introduction have to be in the past > tense and the passive or does it matter? > > From taylormr@plu.edu Thu May 1 18:05:43 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 SAA01637 for ; Thu, 1 May 1997 18:05:42 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IID4JMI3IO00ASRF@plu.edu> for Organic1@rainier.chem.plu.edu; Thu, 1 May 1997 18:01:53 PDT Date: Thu, 01 May 1997 18:01:52 -0700 (PDT) From: "M.Taylor" Subject: Re: your mail In-reply-to: To: smithtw@plu.edu Cc: larsenak@plu.edu, Organic Chemistry 232 Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Yes, the whole formal report has to be in past tense. This is because we have already performed the lab and are just reporting the procedures and results that went on during the lab. Michele On Thu, 1 May 1997 smithtw@plu.edu wrote: > Doesn't it all have to be in past tense? The whole report? > > On Thu, 1 May 1997 larsenak@plu.edu wrote: > > > On the formal lab report, does the introduction have to be in the past > > tense and the passive or does it matter? > > > > > > From joelm@plu.edu Sun May 4 12:16:03 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 MAA22894 for ; Sun, 4 May 1997 12:16:02 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIGZ76B3CM00BSO4@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 4 May 1997 12:12:13 PDT Date: Sun, 04 May 1997 12:12:13 -0700 (PDT) From: super freak Subject: old test To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII will there be one posted (like last time) for this test? lj ~~~~ joelm@plu.edu ~~~~ 'KISS ME BABY, I'M VACINATED!' --another crazy chic From joelm@plu.edu Sun May 4 12:17:08 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 MAA22936 for ; Sun, 4 May 1997 12:17:07 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIGZ8ISYEK00BSO4@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 4 May 1997 12:13:18 PDT Date: Sun, 04 May 1997 12:13:18 -0700 (PDT) From: super freak Subject: review sessions? To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII anyone know if there are review sessions planned. or anyone hosting any? lj ~~~~ joelm@plu.edu ~~~~ 'KISS ME BABY, I'M VACINATED!' --another crazy chic From joelm@plu.edu Sun May 4 12:18:11 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 MAA22965 for ; Sun, 4 May 1997 12:18:11 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIGZ9TT90I00BSO4@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 4 May 1997 12:14:21 PDT Date: Sun, 04 May 1997 12:14:21 -0700 (PDT) From: super freak Subject: this week's lab To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII anyone done it yet? how long did it take, and are there good stopping points in it? thanks! =) lj ~~~~ joelm@plu.edu ~~~~ 'KISS ME BABY, I'M VACINATED!' --another crazy chic From carlisel@plu.edu Sun May 4 12:43:07 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 MAA23090 for ; Sun, 4 May 1997 12:43:07 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIH05OH5J400BQZE@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 4 May 1997 12:39:16 PDT Date: Sun, 04 May 1997 12:39:15 -0700 (PDT) From: carlisel@plu.edu Subject: Re: this week's lab In-reply-to: To: super freak Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Yes, there are two good stopping points so you are able to do it in two or three days. The crystals have to dry overnight, so it must be done in atleast two days. You better allow a lot of time for this lab. I have not yet completed it, but the first two sections (up until I let the crystals dry overnight) took me 4 and a half hours. Good Luck! On Sun, 4 May 1997, super freak wrote: > > anyone done it yet? how long did it take, and are there good stopping > points in it? thanks! =) > > lj > > ~~~~ > joelm@plu.edu > > ~~~~ > 'KISS ME BABY, I'M VACINATED!' --another crazy chic > > > From archerka@plu.edu Sun May 4 15:13:24 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 PAA23846 for ; Sun, 4 May 1997 15:13:23 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIH5E0BLTS00C2X4@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 4 May 1997 15:09:32 PDT Date: Sun, 04 May 1997 15:09:32 -0700 (PDT) From: archerka@plu.edu Subject: Test To: organic chemistry list Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I was wondering if we are expected to memorize all of the numbers (frequency range) for the different groups in an IR Spectrum for the test or if this information will be provided for us. Kristy From fryhle@u.washington.edu Sun May 4 15:24:35 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 PAA23931 for ; Sun, 4 May 1997 15:24:35 -0700 Received: from homer29.u.washington.edu (fryhle@homer29.u.washington.edu [140.142.76.14]) by jason01.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with ESMTP id PAA11640 for ; Sun, 4 May 1997 15:20:46 -0700 Received: from localhost (fryhle@localhost) by homer29.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with SMTP id PAA75186 for ; Sun, 4 May 1997 15:20:46 -0700 Date: Sun, 4 May 1997 15:20:45 -0700 (PDT) From: Craig Fryhle To: Organic Chemistry I List Subject: Exam III Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings. I will post a copy of a previous exam on the organic chemistry bulletin board on Monday. I'll devote my office hours on Monday (12:30 - 2:00) to a review session for the class in Rieke 224. Regarding IR frequencies and 1H and 13C NMR chemical shifts, I will provide Tables 13.2, 13.3, and 13.4 for you with your exam. The less you have to rely on the tables the better, but I do not expect you to memorize in detail the information in those tables. 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 williasl@plu.edu Sun May 4 18:56:48 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 SAA24932 for ; Sun, 4 May 1997 18:56:48 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIHD719C3400C79P@plu.edu> for ORGANIC1@RAINIER.CHEM.PLU.EDU; Sun, 4 May 1997 18:52:58 PDT Date: Sun, 04 May 1997 18:52:58 -0700 (PDT) From: williasl@plu.edu Subject: silylation To: THE ORGANIC CHEMLIST Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Would anyone explain why converting an alcohol to a trimethylsilyl ether makes it much more volatile than it otherwise is? Thanks. From williasl@plu.edu Sun May 4 19:03:16 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 TAA25006 for ; Sun, 4 May 1997 19:03:16 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIHDF1FV3Q00C79P@plu.edu> for ORGANIC1@RAINIER.CHEM.PLU.EDU; Sun, 4 May 1997 18:59:25 PDT Date: Sun, 04 May 1997 18:59:25 -0700 (PDT) From: williasl@plu.edu Subject: reactivity of ethers To: THE ORGANIC CHEMLIST Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Why do ethers resist attack by nucleophiles and bases? Is it because if a nucleophile attacked the electron pairs of the oxygen, the oxygen would have an unstable charge? From triplema@plu.edu Sun May 4 21:13:14 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 VAA25683 for ; Sun, 4 May 1997 21:13:14 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIHHXVRTCG00C4AD@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 4 May 1997 21:09:10 PDT Date: Sun, 04 May 1997 21:09:09 -0700 (PDT) From: Harvey the Wonder Hamster Subject: learning group problem To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII How do you go about synthesizing meso 2,3-butane diol from ethyne and methane. Any help to get me going would be appreciated. Thanks. From boothcj@plu.edu Sun May 4 21:18:47 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 VAA25768 for ; Sun, 4 May 1997 21:18:46 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIHI5XW59S00CFUY@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 4 May 1997 21:14:52 PDT Date: Sun, 04 May 1997 21:14:52 -0700 (PDT) From: boothcj@plu.edu Subject: chpt. 10 LG prob. To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Can someone please help me out with ? #1. We have no idea which way the syntheses should follow. From joelm@plu.edu Sun May 4 21:29:09 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 VAA25850 for ; Sun, 4 May 1997 21:29:08 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIHIIP4TDS00C69P@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 4 May 1997 21:25:10 PDT Date: Sun, 04 May 1997 21:25:09 -0700 (PDT) From: super freak Subject: Re: prob 10.6 In-reply-to: To: Harvey the Wonder Hamster Cc: organic1, ~joelm@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII how do i get the HgOAc off and the H on with the sodium borohydride? thanks lj ~~~~ joelm@plu.edu ~~~~ 'KISS ME BABY, I'M VACINATED!' --another crazy chic From mistkaam@plu.edu Sun May 4 22:02:49 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 WAA26068 for ; Sun, 4 May 1997 22:02:48 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIHJOLF9SC00CFOU@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 4 May 1997 21:58:56 PDT Date: Sun, 04 May 1997 21:58:55 -0700 (PDT) From: mistkaam@plu.edu Subject: Re: this week's lab In-reply-to: To: super freak Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII If you are talking about lab. It took about five hours for the first part and about an hour for the second. There is a stoping point for the first part, but I went strait through. On Sun, 4 May 1997, super freak wrote: > > anyone done it yet? how long did it take, and are there good stopping > points in it? thanks! =) > > lj > > ~~~~ > joelm@plu.edu > > ~~~~ > 'KISS ME BABY, I'M VACINATED!' --another crazy chic > > > From barnetca@plu.edu Mon May 5 00:17:27 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 AAA27054 for ; Mon, 5 May 1997 00:17:26 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIHOEGLMKW00C8QP@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 5 May 1997 00:13:33 PDT Date: Mon, 05 May 1997 00:13:32 -0700 (PDT) From: barnetca@plu.edu Subject: Re: learning group problem In-reply-to: To: Harvey the Wonder Hamster Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII A little help that can start you on your way - If you look at fig.10.3 on page 456, it gives a portion of part I to the chapter 10 L.G. problem! (You said ANY help), hope that will help you! On Sun, 4 May 1997, Harvey the Wonder Hamster wrote: > How do you go about synthesizing meso 2,3-butane diol from ethyne and > methane. Any help to get me going would be appreciated. Thanks. > > From barnetca@plu.edu Mon May 5 00:19:54 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 AAA27091 for ; Mon, 5 May 1997 00:19:54 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIHOHGW1K800C8QP@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 5 May 1997 00:15:58 PDT Date: Mon, 05 May 1997 00:15:57 -0700 (PDT) From: barnetca@plu.edu Subject: Re: chpt. 10 LG prob. In-reply-to: To: boothcj@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII For #1 on the chapter 10 learning group problem, page 455-6 gives figures that might help you! On Sun, 4 May 1997 boothcj@plu.edu wrote: > Can someone please help me out with ? #1. We have no idea which way the > syntheses should follow. > > From hiattzr@plu.edu Mon May 5 13:26:41 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 NAA00953 for ; Mon, 5 May 1997 13:26:40 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIIFXYOCBK00CJZT@plu.edu> for ORGANIC1@rainier.chem.plu.edu; Mon, 5 May 1997 13:22:45 PDT Date: Mon, 05 May 1997 13:22:44 -0700 (PDT) From: hiattzr@plu.edu Subject: Re: reactivity of ethers In-reply-to: To: williasl@plu.edu Cc: THE ORGANIC CHEMLIST Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII williasl, I wondered the same thing about why ethers resist attack when I read that. My guess is that the unshared electron pairs of the oxygen would repel the unshared electron pairs on any nucleophile or base that would try to attack. When an ether becomes protonated, one of the unshared electron pairs of the oxygen becomes bonded to the proton, and the molecule becomes much more positively charged in that region. I hope this helps. On Sun, 4 May 1997 williasl@plu.edu wrote: > > > Why do ethers resist attack by nucleophiles and bases? Is it because if a > nucleophile attacked the electron pairs of the oxygen, the oxygen would > have an unstable charge? > > > From blackkl@plu.edu Mon May 5 14:26:31 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 OAA01306 for ; Mon, 5 May 1997 14:26:30 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIII280TCO00C3PH@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 5 May 1997 14:22:39 PDT Date: Mon, 05 May 1997 14:22:39 -0700 (PDT) From: blackkl@plu.edu To: Organic Chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Can someone explain to me how you know when to use which reactants in a mechanism..when THF/Hg(O2CCF3)2 is used and when NaBH4, OH- is used..this keeps confusing me so any help would be appreciated, if anyone has a little trick or special hint that would be great! Thanks! From blackkl@plu.edu Mon May 5 14:29:23 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 OAA01343 for ; Mon, 5 May 1997 14:29:23 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIII5QMOWU00C3PH@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 5 May 1997 14:25:29 PDT Date: Mon, 05 May 1997 14:25:29 -0700 (PDT) From: blackkl@plu.edu To: Organic Chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Are less substituted carbon atoms and more substituted carbon atoms the same thing as fewer Hydrogen atoms attached to carbons or the most Hydrogen atoms that are attached to a Carbon? Is there any difference that I am missing that distinguishes the two? Does less and more substituted only relate to double bonded carbons?Thanks for any help anyone can give! From muellesb@plu.edu Mon May 5 15:34:07 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 PAA01719 for ; Mon, 5 May 1997 15:34:06 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIIKEONEO000C1O8@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 5 May 1997 15:30:05 PDT Date: Mon, 05 May 1997 15:30:01 -0700 (PDT) From: Firefly Subject: Re: your mail In-reply-to: To: blackkl@plu.edu Cc: Organic Chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII If you assume that hydrogen atoms are attached to carbon atoms (being that this is organic chem, and we're dealing with a lot of hydrocarbons), then anything attached to a carbon that isn't a hydrogen is a substitution. That means that more hydrogen=less substitution. On Mon, 5 May 1997 blackkl@plu.edu wrote: > Are less substituted carbon atoms and more substituted carbon atoms the > same thing as fewer Hydrogen atoms attached to carbons or the most > Hydrogen atoms that are attached to a Carbon? Is there any difference that > I am missing that distinguishes the two? Does less and more substituted > only relate to double bonded carbons?Thanks for any help anyone can give! > > From davidsct@plu.edu Mon May 5 16:13:16 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 QAA01929 for ; Mon, 5 May 1997 16:13:15 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIILREE83K00DGA2@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 5 May 1997 16:09:17 PDT Date: Mon, 05 May 1997 16:09:15 -0700 (PDT) From: davidsct@plu.edu Subject: Re: your mail In-reply-to: To: blackkl@plu.edu Cc: Organic Chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII blackkl- The reactants described below are used in adding alcohols to alkenes through oxymercuration and Demercuration. the initial mixture THF and water plus the mercuric acetate produces a hydroxyalkyl compound. The sodium borohydride reduces the acetoxymercuri group, replacing it with hydrogen. So, when you are going from an alkene to an alcohol through oxymercuration-Demurcuration, not from hydration of an alkene, you use those such mixtures you described below. A good way to understand just what takes place and where is by looking on page 423, and 424. A mechanism is shown in detail on what is applied where, and why. cd On Mon, 5 May 1997 blackkl@plu.edu wrote: > Can someone explain to me how you know when to use which reactants in a > mechanism..when THF/Hg(O2CCF3)2 is used and when NaBH4, OH- is used..this > keeps confusing me so any help would be appreciated, if anyone has a > little trick or special hint that would be great! Thanks! > > From hardinkm@plu.edu Mon May 5 18:11:58 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 SAA02730 for ; Mon, 5 May 1997 18:11:55 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIIPVSEB0W00D38J@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 5 May 1997 18:07:23 PDT Date: Mon, 05 May 1997 18:07:19 -0700 (PDT) From: cancel Subject: Re: your mail In-reply-to: To: Firefly Cc: blackkl@plu.edu, Organic Chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII As far as substitution goes, can't carbon substituents refer to anything which is attached to the carbon , not necessarily only hydrogen? That's what I thought at least, but someone correct me if I'm wrong. Thanks--- On Mon, 5 May 1997, Firefly wrote: > If you assume that hydrogen atoms are attached to carbon atoms (being that > this is organic chem, and we're dealing with a lot of hydrocarbons), then > anything attached to a carbon that isn't a hydrogen is a substitution. > That means that more hydrogen=less substitution. > > > On Mon, 5 May 1997 blackkl@plu.edu wrote: > > > Are less substituted carbon atoms and more substituted carbon atoms the > > same thing as fewer Hydrogen atoms attached to carbons or the most > > Hydrogen atoms that are attached to a Carbon? Is there any difference that > > I am missing that distinguishes the two? Does less and more substituted > > only relate to double bonded carbons?Thanks for any help anyone can give! > > > > > > From williasl@plu.edu Mon May 5 18:59:38 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 SAA02997 for ; Mon, 5 May 1997 18:59:37 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIIRKCQ0VK00BWLE@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 5 May 1997 18:55:24 PDT Date: Mon, 05 May 1997 18:55:22 -0700 (PDT) From: williasl@plu.edu Subject: Re: your mail In-reply-to: To: cancel Cc: Firefly , blackkl@plu.edu, Organic Chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I thought that when dealing with Markovnikov addition, carbon substituents refer to everything but hydrogen. A less substituted carbon would be the carbon with the most hydrogens attached, and the most substituted carbon would be the carbon with the least number of hydrogens attatched. Does that make sense? On Mon, 5 May 1997, cancel wrote: > As far as substitution goes, can't carbon substituents refer to anything > which is attached to the carbon , not necessarily only hydrogen? That's > what I thought at least, but someone correct me if I'm wrong. Thanks--- > > On Mon, 5 May 1997, Firefly wrote: > > > If you assume that hydrogen atoms are attached to carbon atoms (being that > > this is organic chem, and we're dealing with a lot of hydrocarbons), then > > anything attached to a carbon that isn't a hydrogen is a substitution. > > That means that more hydrogen=less substitution. > > > > > > On Mon, 5 May 1997 blackkl@plu.edu wrote: > > > > > Are less substituted carbon atoms and more substituted carbon atoms the > > > same thing as fewer Hydrogen atoms attached to carbons or the most > > > Hydrogen atoms that are attached to a Carbon? Is there any difference that > > > I am missing that distinguishes the two? Does less and more substituted > > > only relate to double bonded carbons?Thanks for any help anyone can give! > > > > > > > > > > > > From williasl@plu.edu Mon May 5 21:55:13 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 VAA03912 for ; Mon, 5 May 1997 21:55:12 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIIXPJAXHY00CAS2@plu.edu> for ORGANIC1@RAINIER.CHEM.PLU.EDU; Mon, 5 May 1997 21:51:20 PDT Date: Mon, 05 May 1997 21:51:20 -0700 (PDT) From: williasl@plu.edu Subject: signal splitting To: THE ORGANIC CHEMLIST Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Are there two different types of signal splitting, one having to do with equivalent H's and the other with non-equivalent H's, the difference being that you use the n+1 rule with equivalent H's? From bowersmy@plu.edu Mon May 5 23:02:03 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 XAA04345 for ; Mon, 5 May 1997 23:02:02 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIJ026EII800C9Z4@plu.edu> for ORGANIC1@rainier.chem.plu.edu; Mon, 5 May 1997 22:58:05 PDT Date: Mon, 05 May 1997 22:58:01 -0700 (PDT) From: bowersmy@plu.edu Subject: Re: signal splitting In-reply-to: To: williasl@plu.edu Cc: THE ORGANIC CHEMLIST Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Equivalent H's don't spit each other. Signal splitting only arises from hydrogen attractions on adjacent C atoms. Equivalent atoms are attached to the same C atom. On Mon, 5 May 1997 williasl@plu.edu wrote: > > > Are there two different types of signal splitting, one having to do with > equivalent H's and the other with non-equivalent H's, the difference being > that you use the n+1 rule with equivalent H's? > > From bowersmy@plu.edu Mon May 5 23:18:59 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 XAA04453 for ; Mon, 5 May 1997 23:18:57 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIJ0MZ0VS000CSOX@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 5 May 1997 23:14:49 PDT Date: Mon, 05 May 1997 23:14:48 -0700 (PDT) From: bowersmy@plu.edu Subject: mercuration To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Does mercuration take place as a syn addition? From storeyad@plu.edu Tue May 6 00:35:37 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 AAA05141 for ; Tue, 6 May 1997 00:35:36 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIJ3BAWI9C00D3EU@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 6 May 1997 00:31:41 PDT Date: Tue, 06 May 1997 00:31:40 -0700 (PDT) From: madam president Subject: Re: mercuration In-reply-to: To: bowersmy@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII On Mon, 5 May 1997 bowersmy@plu.edu wrote: > > > Does mercuration take place as a syn addition? > > Mercuration is Markovnikov addition. and it wouldn't really matter if it was syn or anti addition, because only the intermediate step has two additions. The final product seems to mainly be syn (incld. H) in all of the examples and what i understand. please correct me if i am wrong, but i think that is right. From harriscr@plu.edu Tue May 6 00:58:59 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 AAA05261 for ; Tue, 6 May 1997 00:58:58 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIJ459FSRI00CYMK@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 6 May 1997 00:55:03 PDT Date: Tue, 06 May 1997 00:55:02 -0700 (PDT) From: harriscr@plu.edu Subject: Re: mercuration In-reply-to: To: bowersmy@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Hi, If you take a look at page 425 in your text the mechanism for Oxymercuration shows that it isn't specifically a syn addition. I suppose that one the HgOAc group is replaced by a H it doesn't matter if it is syn addition because the single bonds can freely rotate. I hope this helps. Clayton On Mon, 5 May 1997 bowersmy@plu.edu wrote: > > > Does mercuration take place as a syn addition? > > From harriscr@plu.edu Tue May 6 01:02:11 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 BAA05314 for ; Tue, 6 May 1997 01:02:10 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIJ49AXEL200CYMK@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 6 May 1997 00:58:17 PDT Date: Tue, 06 May 1997 00:58:17 -0700 (PDT) From: harriscr@plu.edu Subject: SYNTHESIS OF ETHERS To: Organic chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Hi Does anyone know when the the conditions of H2SO4, 140 degrees celcius is favored for the formation of ethers? Clayton From petershm@plu.edu Tue May 6 02:13:01 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 CAA05645 for ; Tue, 6 May 1997 02:13:00 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIJ6Q4S9WG00C8L7@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 6 May 1997 02:09:08 PDT Date: Tue, 06 May 1997 02:09:08 -0700 (PDT) From: petershm@plu.edu In-reply-to: Cc: Organic chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Does anyone know how long the pre-lab takes for this lab? I heard the lab takes about 6 hours, is that accurate? ~HP From fryhle@u.washington.edu Tue May 6 10:13:44 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 KAA08147 for ; Tue, 6 May 1997 10:13:43 -0700 Received: from homer29.u.washington.edu (fryhle@homer29.u.washington.edu [140.142.76.14]) by jason02.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with ESMTP id KAA16158; Tue, 6 May 1997 10:09:52 -0700 Received: from localhost (fryhle@localhost) by homer29.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with SMTP id KAA23502; Tue, 6 May 1997 10:09:51 -0700 Date: Tue, 6 May 1997 10:09:51 -0700 (PDT) From: Craig Fryhle To: bowersmy@plu.edu cc: organic1 Subject: Re: mercuration In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings. In addition to the other replies that have come in, let me add this note. The oxymercuration step (first step of oxymercuration-demurcuration) does proceed in syn fashion. BUT, the replacement of the mercury group in the NaBH4 step (second step) puts the hydrogen on without retention of configuration with respect to the mercury. This is in contrast to hydroboration-oxidation, where replacement of the boron by OH occurs with retention of configuration, i.e. the OH replaces the B without changing the configuration. Thus, hydroboration-oxidation proceeds with overall syn addition of the H and OH. In the demercuration step (NaBH4) of oxymercuration-demurcuration, replacement of the Hg group is not stereospecific, so the addition can be a mixture of syn and anti. CBF On Mon, 5 May 1997 bowersmy@plu.edu wrote: > > > Does mercuration take place as a syn addition? > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 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 May 6 10:21:49 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 KAA08244 for ; Tue, 6 May 1997 10:21:48 -0700 Received: from homer29.u.washington.edu (fryhle@homer29.u.washington.edu [140.142.76.14]) by jason05.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with ESMTP id KAA19056; Tue, 6 May 1997 10:17:57 -0700 Received: from localhost (fryhle@localhost) by homer29.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with SMTP id KAA106526; Tue, 6 May 1997 10:17:56 -0700 Date: Tue, 6 May 1997 10:17:55 -0700 (PDT) From: Craig Fryhle To: williasl@plu.edu cc: cancel , Firefly , blackkl@plu.edu, Organic Chemistry Subject: Carbon substitution In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings. There has been lots of good discussion about this topic. Here's my $.02. By "more or less substituted" we are referring to the number of carbon groups bonded to an alkene or a carbocation. This phrase does not mean any substituent, for example halogens, hydroxyls, etc. We need to pay attention to the number of carbon groups bonded at alkene carbons in order to apply Markovnikov's rule and to evaluate the relative stability of a carbocation that might be formed at one end of a former alkene vs the other end. Or in general, to evaluate which carbon could better accomodate a positive charge (full or partial) - the more highly substituted with carbon groups a particular carbon is, the more able it will be to accomodate a positive charge. CBF On Mon, 5 May 1997 williasl@plu.edu wrote: > > I thought that when dealing with Markovnikov addition, carbon substituents > refer to everything but hydrogen. A less substituted carbon would be the > carbon with the most hydrogens attached, and the most substituted carbon > would be the carbon with the least number of hydrogens attatched. > Does that make sense? > > > On Mon, 5 May 1997, cancel wrote: > > > As far as substitution goes, can't carbon substituents refer to anything > > which is attached to the carbon , not necessarily only hydrogen? That's > > what I thought at least, but someone correct me if I'm wrong. Thanks--- > > > > On Mon, 5 May 1997, Firefly wrote: > > > > > If you assume that hydrogen atoms are attached to carbon atoms (being that > > > this is organic chem, and we're dealing with a lot of hydrocarbons), then > > > anything attached to a carbon that isn't a hydrogen is a substitution. > > > That means that more hydrogen=less substitution. > > > > > > > > > On Mon, 5 May 1997 blackkl@plu.edu wrote: > > > > > > > Are less substituted carbon atoms and more substituted carbon atoms the > > > > same thing as fewer Hydrogen atoms attached to carbons or the most > > > > Hydrogen atoms that are attached to a Carbon? Is there any difference that > > > > I am missing that distinguishes the two? Does less and more substituted > > > > only relate to double bonded carbons?Thanks for any help anyone can give! > > > > > > > > > > > > > > > > > > > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 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 May 6 10:46:21 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 KAA08445 for ; Tue, 6 May 1997 10:46:18 -0700 Received: from homer29.u.washington.edu (fryhle@homer29.u.washington.edu [140.142.76.14]) by jason01.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with ESMTP id KAA13464; Tue, 6 May 1997 10:42:27 -0700 Received: from localhost (fryhle@localhost) by homer29.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with SMTP id KAA65306; Tue, 6 May 1997 10:42:25 -0700 Date: Tue, 6 May 1997 10:42:25 -0700 (PDT) From: Craig Fryhle To: hiattzr@plu.edu cc: williasl@plu.edu, THE ORGANIC CHEMLIST Subject: Re: reactivity of ethers In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings. There's been some interesting converstion about reactivity of ethers. Here's a few more comments. Consider what the leaving group would be if an ether were attacked by a nucleophile without first protonating the ether oxygen. How would the group you displaced rate as far as leaving groups go? (This scenario is for nucleophilic attack under basic/anionic conditions on the carbon of an ether functional group). Now, consider the same reaction after first protonating the ether oxygen, or in some way providing it a formal positive charge. If a nucleophile attacks a carbon of the ether group in this state, how does the group being displaced rate as a leaving group? This should help explain why ethers do not react under basic conditions. Now, consider the specific example of epoxides (oxiranes) as ethers that can undergo nucleophilic ring opening. You may have noticed that they *do* undergo ring opening under *basic* conditions, and produce the very type of leaving group that you concluded above was a bad leaving group. But, the difference here is that the epoxide is much more prone to react because opening the epoxide releaves the significant angle strain of a three-membered ring. So, an epoxide can be opened by nucleophilic attack under either basic/anionic conditions or acidic conditions, whereas other types of ethers do not react under basic conditions (for the reasons you came upon above). Food for thought, and hopefully clarification... CBF On Mon, 5 May 1997 hiattzr@plu.edu wrote: > williasl, > I wondered the same thing about why ethers resist attack when I > read that. My guess is that the unshared electron pairs of the oxygen > would repel the unshared electron pairs on any nucleophile or base that > would try to attack. When an ether becomes protonated, one of the > unshared electron pairs of the oxygen becomes bonded to the proton, and > the molecule becomes much more positively charged in that region. I > hope this helps. > > On Sun, 4 May 1997 williasl@plu.edu wrote: > > > > > > > Why do ethers resist attack by nucleophiles and bases? Is it because if a > > nucleophile attacked the electron pairs of the oxygen, the oxygen would > > have an unstable charge? > > > > > > > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 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 mistkaam@plu.edu Tue May 6 10:51:19 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 KAA08537 for ; Tue, 6 May 1997 10:51:19 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIJOTOLNQO00D9EI@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 6 May 1997 10:47:24 PDT Date: Tue, 06 May 1997 10:47:23 -0700 (PDT) From: mistkaam@plu.edu Subject: Re: your mail In-reply-to: To: petershm@plu.edu Cc: Organic chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Prelab doesn't take that long. There are about seven reagents. Lab took me five hours for the first part and about an hour for the second part, so about six hours is accurate. On Tue, 6 May 1997 petershm@plu.edu wrote: > Does anyone know how long the pre-lab takes for this lab? I heard the lab > takes about 6 hours, is that accurate? ~HP > > From fryhle@u.washington.edu Tue May 6 12:31:32 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 MAA09067 for ; Tue, 6 May 1997 12:31:32 -0700 Received: from homer04.u.washington.edu (fryhle@homer04.u.washington.edu [140.142.76.11]) by jason04.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with ESMTP id MAA18354 for ; Tue, 6 May 1997 12:27:41 -0700 Received: from localhost (fryhle@localhost) by homer04.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with SMTP id MAA36520 for ; Tue, 6 May 1997 12:27:40 -0700 Date: Tue, 6 May 1997 12:27:40 -0700 (PDT) From: Craig Fryhle To: Organic Chemistry I List Subject: Exam III Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings, everyone. Just a reminder that I'll have the exams available at 7:30 in Leraas on Wednesday a.m. As you study, you might find helpful the Summary of Reactions by Type handout that I gave you at the beginning of the semester. It could serve to jog your memory about reactions you have learned, as well as provide an overview of typical conditions, regiochemistry, and stereochemistry associated with each reaction. I also suggest a good night's sleep as the best way to sharpen your mind for the morning! 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 erickstd@plu.edu Tue May 6 14:41:41 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 OAA09841 for ; Tue, 6 May 1997 14:41:40 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIJWVBCS1S00DV4L@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 6 May 1997 14:37:46 PDT Date: Tue, 06 May 1997 14:37:46 -0700 (PDT) From: THE PENGUIN Subject: Special Topics? To: O-Chem List Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Will this exam cover special topics C and D? thanks -TDE XXXX X XXX/ XXXXXX\ XXXX XXXXX# X**XX### X***X##### X***X##### X**XX##### *XXXX### XXXXXX ^^^^^^^^^ Dooby Dooby Doo!! From baileyle@plu.edu Tue May 6 14:57:03 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 OAA09938 for ; Tue, 6 May 1997 14:57:02 -0700 Received: from Hind215b.PLU.EDU by plu.edu (PMDF V5.1-5 #17589) with SMTP id <01IIJXEDLP4600DJLD@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 6 May 1997 14:53:09 PDT Date: Tue, 06 May 1997 14:51:54 -0700 From: Lora Bailey Subject: Re: Special Topics? To: organic1, THE PENGUIN Reply-to: baileyle@plu.edu Message-id: <336FA7FA.48EC@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: THE PENGUIN wrote: > > Will this exam cover special topics C and D? > thanks > -TDE > XXXX > X XXX/ > XXXXXX\ > XXXX > XXXXX# > X**XX### > X***X##### > X***X##### > X**XX##### > *XXXX### > XXXXXX > ^^^^^^^^^ > > Dooby Dooby Doo!! I don't think they will be on the exam because they aren't on the study guides. Someone please tell me if I'm wrong. Lora From hoffmasb@plu.edu Tue May 6 15:10:33 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 PAA10070 for ; Tue, 6 May 1997 15:10:31 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIJXV2DR0W00CQRK@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 6 May 1997 15:06:36 PDT Date: Tue, 06 May 1997 15:06:35 -0700 (PDT) From: hoffmasb@plu.edu Subject: this weeks lab To: organic chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Is this lab due this Friday night, or is it due next Monday like the others in the past? Sara From harstalj@plu.edu Tue May 6 15:27:29 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 PAA10227 for ; Tue, 6 May 1997 15:27:28 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIJYGUETCG001IC0@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 6 May 1997 15:23:25 PDT Date: Tue, 06 May 1997 15:23:22 -0700 (PDT) From: FAT-N-SASSY Subject: way back when To: organic1 Cc: HARSTALJ@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII HI I TRIED TO SEND THIS A FEW DAYS AGO BUT I DON'T THINK IT MADE IT TO THE LIST. IF IT DID, JUST IGNORE IT. IF IT DIDN'T HERE IT IS! THANKS, LESLIE I have a question from ch. 13 and I know that was eons and eons ago, but please somebody answer anyway! Ok, here is my question: in exercise 20 we are supposed to determine structures for certain compounds. Now one of the compounds is said to give a proton-decoupled C13 specturm with two SINGLETS, but the answer book has the structure of this compound drawn out as a cyclohexadiene (that's a six-membered ring with only two double bonds, on opposite sides of the ring from each other.) I'm confused because I thought that singlets resulted when there weren't any hydrogens on the carbons adjacent to the one with the hydrogen producing the reading, but this cyclohexadiene would have at least one hydrogen attached to every carbon, and no matter which hydrogen you chose, there are at least three hydrogens on adjacent carbons... The spectrum I would guess would result from this thing would be one doublet and one triplet, and NO singlets. Can someone help? thanks, Leslie From HARSTALJ@plu.edu Tue May 6 15:39:10 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 PAA10332 for ; Tue, 6 May 1997 15:39:09 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIJYJNX2YO001IC0@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 6 May 1997 15:35:15 PDT Date: Tue, 06 May 1997 15:35:11 -0700 (PDT) From: FAT-N-SASSY Subject: Oxidation To: organic1 Message-id: <01IIJYJNYAAA001IC0@plu.edu> X-VMS-To: IN%"organic1@rainier.chem.plu.edu" X-VMS-Cc: HARSTALJ MIME-version: 1.0 Content-type: TEXT/PLAIN; CHARSET=US-ASCII Something I'm confused by (can someone help)? ... In the text book on page 430 there is a "A Mechanism for the Oxidation" box with a picture of an oxidation reaction in it. In the text under the box, it says that "repetitions of these two steps occur until all of the alkyl groups have become attached to oxygen atioms. The result isthe formation of a trialkyl borate." Right after that it says that the next step in this preparation of an alcohol is the replacement of the boron atom with a hydrogen through "basic hydrolysis to produce THREE molecules of the alcohol and a borate ion." So I'm wondering why, on the next page, the picture of the stereochemistry of the same reaction only shows the boron atom bonded to ONE R group when the hydrolysis occurs. Did I miss something? Can anyone explain this to me? thanks! Leslie From weinmadj@plu.edu Tue May 6 15:58:29 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 PAA10502 for ; Tue, 6 May 1997 15:58:28 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIJZJFWUAO00DWFH@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 6 May 1997 15:54:33 PDT Date: Tue, 06 May 1997 15:54:30 -0700 (PDT) From: weinmadj@plu.edu Subject: Re: this weeks lab In-reply-to: To: hoffmasb@plu.edu Cc: organic chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII This lab is due on Monday as usual. It's no different from any of the other labs. David On Tue, 6 May 1997 hoffmasb@plu.edu wrote: > > Is this lab due this Friday night, or is it due next Monday like the > others in the past? > Sara > > From weinmadj@plu.edu Tue May 6 16:01:51 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 QAA10595 for ; Tue, 6 May 1997 16:01:50 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIJZN37KIW00DWFH@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 6 May 1997 15:57:30 PDT Date: Tue, 06 May 1997 15:57:28 -0700 (PDT) From: weinmadj@plu.edu Subject: references (fwd) To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Just ignore this message. I sent it out a few days ago and it was never added to the TOJC list for April. Sorry. ---------- Forwarded message ---------- Date: Wed, 30 Apr 1997 19:45:59 -0700 (PDT) From: weinmadj@plu.edu To: fryhle@u.washington.edu, organic1@rainier.chem.plu.edu Subject: references 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 callahnl@plu.edu Tue May 6 16:54:50 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 QAA11007 for ; Tue, 6 May 1997 16:54:49 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIK1IDR99C00E2JG@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 6 May 1997 16:50:56 PDT Date: Tue, 06 May 1997 16:50:54 -0700 (PDT) From: "D'oh" Subject: Re: way back when In-reply-to: To: FAT-N-SASSY Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII hey Leslie, There are only two C13 singlets because that is all that is in the ring. C13 measure the different carbons present, and does not tell you how many actually exist. What you are thinking of is H1. Here a singlet would mean that there were no hydrogens in the adjacent hydrogens. -nick On Tue, 6 May 1997, FAT-N-SASSY wrote: > HI I TRIED TO SEND THIS A FEW DAYS AGO BUT I DON'T THINK IT MADE IT TO THE > LIST. IF IT DID, JUST IGNORE IT. IF IT DIDN'T HERE IT IS! > THANKS, > LESLIE > > I have a question from ch. 13 and I know that was eons and eons ago, but > please somebody answer anyway! > > Ok, here is my question: > in exercise 20 we are supposed to determine structures for certain > compounds. Now one of the compounds is said to give a proton-decoupled C13 > specturm with two SINGLETS, but the answer book has the structure of this > compound drawn out as a cyclohexadiene (that's a six-membered ring with > only two double bonds, on opposite sides of the ring from each other.) I'm > confused because I thought that singlets resulted when there weren't any > hydrogens on the carbons adjacent to the one with the hydrogen producing > the reading, but this cyclohexadiene would have at least one hydrogen > attached to every carbon, and no matter which hydrogen you chose, there > are at least three hydrogens on adjacent carbons... The spectrum I would > guess would result from this thing would be one doublet and one triplet, > and NO singlets. > > Can someone help? > > thanks, > Leslie > > > From taylormr@plu.edu Tue May 6 16:58:29 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 QAA11096 for ; Tue, 6 May 1997 16:58:28 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIK1MXMIHS009JHH@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 6 May 1997 16:54:36 PDT Date: Tue, 06 May 1997 16:54:34 -0700 (PDT) From: "M.Taylor" Subject: Re: Special Topic In-reply-to: <336FA7FA.48EC@plu.edu> To: Lora Bailey Cc: organic1, THE PENGUIN Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Exam 3 should only cover chapters 13, 9 and 10. but if it is over the special topics, please let me know. michele On Tue, 6 May 1997, Lora Bailey wrote: > THE PENGUIN wrote: > > > > Will this exam cover special topics C and D? > > thanks > > -TDE > > XXXX > > X XXX/ > > XXXXXX\ > > XXXX > > XXXXX# > > X**XX### > > X***X##### > > X***X##### > > X**XX##### > > *XXXX### > > XXXXXX > > ^^^^^^^^^ > > > > Dooby Dooby Doo!! > > I don't think they will be on the exam because they aren't on the study > guides. Someone please tell me if I'm wrong. Lora > From petershm@plu.edu Tue May 6 17:32:15 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 RAA11394 for ; Tue, 6 May 1997 17:32:14 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIK2TK97BA00DDLX@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 6 May 1997 17:28:09 PDT Date: Tue, 06 May 1997 17:28:09 -0700 (PDT) From: petershm@plu.edu In-reply-to: Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII So if chapter 11 isn't on this test is it just added into the final? And i was wondering if the final is going to be standarized like chem 120? thanks _HP From weinmadj@plu.edu Tue May 6 17:46:23 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 RAA11535 for ; Tue, 6 May 1997 17:46:22 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIK3BCF3KW00D32P@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 6 May 1997 17:42:30 PDT Date: Tue, 06 May 1997 17:42:29 -0700 (PDT) From: weinmadj@plu.edu Subject: Re: your mail In-reply-to: To: petershm@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Someone who had organic last semester said that Fryhle gives a test like the rest of the tests. I also heard that the organic II test is standardized since Organic II is the second part in a sequence. David On Tue, 6 May 1997 petershm@plu.edu wrote: > So if chapter 11 isn't on this test is it just added into the final? And i > was wondering if the final is going to be standarized like chem 120? > thanks _HP > > From taylormr@plu.edu Tue May 6 18:26:31 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 SAA11780 for ; Tue, 6 May 1997 18:26:30 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIK4PX645S00D9XD@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 6 May 1997 18:22:31 PDT Date: Tue, 06 May 1997 18:22:29 -0700 (PDT) From: "M.Taylor" Subject: Re: your mail In-reply-to: To: petershm@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII yeah, that's what i thought. Chapter 11 will be dealt with after exam III and the final is going to be a cumulative final just like chem 120. michele On Tue, 6 May 1997 petershm@plu.edu wrote: > So if chapter 11 isn't on this test is it just added into the final? And i > was wondering if the final is going to be standarized like chem 120? > thanks _HP > > From fryhle@u.washington.edu Tue May 6 18:28:12 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 SAA11813 for ; Tue, 6 May 1997 18:28:11 -0700 Received: from homer35.u.washington.edu (fryhle@homer35.u.washington.edu [140.142.78.18]) by jason01.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with ESMTP id SAA11244; Tue, 6 May 1997 18:24:20 -0700 Received: from localhost (fryhle@localhost) by homer35.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with SMTP id SAA60386; Tue, 6 May 1997 18:24:19 -0700 Date: Tue, 6 May 1997 18:24:19 -0700 (PDT) From: Craig Fryhle To: hoffmasb@plu.edu cc: organic chemistry Subject: Re: this weeks lab In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII The Grignard lab is due next Monday at 6, like the other regular lab reports. CBF On Tue, 6 May 1997 hoffmasb@plu.edu wrote: > > Is this lab due this Friday night, or is it due next Monday like the > others in the past? > 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 davidsct@plu.edu Tue May 6 19:04:47 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 TAA12122 for ; Tue, 6 May 1997 19:04:45 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIK62B6M8Q00BRCK@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 6 May 1997 19:00:45 PDT Date: Tue, 06 May 1997 19:00:43 -0700 (PDT) From: davidsct@plu.edu Subject: Re: Oxidation In-reply-to: <01IIJYJNYAAA001IC0@plu.edu> To: FAT-N-SASSY Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Leslie- I believe the reason the mechanism differs from what is said in the text is because you are just supposed to assume that the mechanism being shown repeats itself two more times, thus ending up with Trialkyl borate. So the mechanism shows only one R group bonding, and the other two times are assumed to have happened in the same fashion. cd On Tue, 6 May 1997, FAT-N-SASSY wrote: > Something I'm confused by (can someone help)? ... > > In the text book on page 430 there is a "A Mechanism for the Oxidation" box > with a picture of an oxidation reaction in it. In the text under the box, it > says that "repetitions of these two steps occur until all of the alkyl groups > have become attached to oxygen atioms. The result isthe formation of a trialkyl > borate." Right after that it says that the next step in this preparation of an > alcohol is the replacement of the boron atom with a hydrogen through "basic > hydrolysis to produce THREE molecules of the alcohol and a borate ion." So I'm > wondering why, on the next page, the picture of the stereochemistry of the same > reaction only shows the boron atom bonded to ONE R group when the hydrolysis > occurs. Did I miss something? Can anyone explain this to me? > > thanks! > Leslie > From erickstd@plu.edu Tue May 6 19:11:07 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 TAA12240 for ; Tue, 6 May 1997 19:11:05 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIK6ACNX5S00D3YX@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 6 May 1997 19:07:12 PDT Date: Tue, 06 May 1997 19:07:12 -0700 (PDT) From: THE PENGUIN Subject: Dry Ice To: O-Chem List Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I haven't done my lab yet this week, but i am curious how we are to transfer the dry ice to a test tube and weigh it without all of it subliming into the air. -TDE ps. Raisins...call me! XXXX X XXX/ XXXXXX\ XXXX XXXXX# X**XX### X***X##### X***X##### X**XX##### *XXXX### XXXXXX ^^^^^^^^^ Dooby Dooby Doo!! From carlisel@plu.edu Tue May 6 20:30:29 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 UAA12699 for ; Tue, 6 May 1997 20:30:27 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIK91PSAXS00DTPG@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 6 May 1997 20:26:33 PDT Date: Tue, 06 May 1997 20:26:32 -0700 (PDT) From: carlisel@plu.edu Subject: Re: Dry Ice In-reply-to: To: THE PENGUIN Cc: O-Chem List Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Just weigh the dry ice as quickly as possible in the beaker and add your product to this beaker. If you act quickly only a small amount will sublime. On Tue, 6 May 1997, THE PENGUIN wrote: > I haven't done my lab yet this week, but i am curious how we are to > transfer the dry ice to a test tube and weigh it without all of it > subliming into the air. > -TDE > ps. Raisins...call me! > XXXX > X XXX/ > XXXXXX\ > XXXX > XXXXX# > X**XX### > X***X##### > X***X##### > X**XX##### > *XXXX### > XXXXXX > ^^^^^^^^^ > > Dooby Dooby Doo!! > > From HARSTALJ@plu.edu Wed May 7 07:10:18 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 HAA16282 for ; Wed, 7 May 1997 07:10:16 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIKV2MYPZK00D214@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 7 May 1997 07:06:25 PDT Date: Wed, 07 May 1997 07:06:24 -0700 (PDT) From: FAT-N-SASSY Subject: Williamson Synthesis To: organic1 Message-id: <01IIKV2MZNWI00D214@plu.edu> X-VMS-To: IN%"organic1@rainier.chem.plu.edu" X-VMS-Cc: HARSTALJ MIME-version: 1.0 Content-type: TEXT/PLAIN; CHARSET=US-ASCII In the answer book, question 42 b, a reaction is shown where a williamson synthesis performed on tert-Butyl bromide yields an alkene. I thought Williamson syntheses were supposed to create ethers... ??? Does anyone know how this happens? -Leslie From HARSTALJ@plu.edu Wed May 7 07:21:54 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 HAA16386 for ; Wed, 7 May 1997 07:21:53 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIKVNT9M4000DVIW@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 7 May 1997 07:18:01 PDT Date: Wed, 07 May 1997 07:18:01 -0700 (PDT) From: FAT-N-SASSY Subject: a study technique To: organic1 Message-id: <01IIKVNTAALU00DVIW@plu.edu> X-VMS-To: IN%"organic1@rainier.chem.plu.edu" X-VMS-Cc: HARSTALJ MIME-version: 1.0 Content-type: TEXT/PLAIN; CHARSET=US-ASCII that might really help some of you cement all those reactions in your brains for the final: go to the bookstore and buy a few big sheets of paper or poster-board and have it laminated in the library. Get a few of those overhead pens (preferably in different colors, it's more fun) and draw out the reaction mechanisms on them a few times. For some reason, using big poster board and colored pens really helps me to remember the details of the reactions more and not to confuse everything -- much more than just trying to draw them out on pieces of notebook paper. This would probably be really fun to do in group study sessions, too. Just a thought. Good luck studying!!! -Leslie From holsinal@plu.edu Wed May 7 09:20:55 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 JAA17073 for ; Wed, 7 May 1997 09:20:54 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIKZY125L000EK46@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 7 May 1997 09:17:02 PDT Date: Wed, 07 May 1997 09:17:02 -0700 (PDT) From: holsinal@plu.edu To: Organic Chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I was wondering is the final going to be comprehensive? From holsinal@plu.edu Wed May 7 09:22:26 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 JAA17112 for ; Wed, 7 May 1997 09:22:26 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIL00VU8XM00EK46@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 7 May 1997 09:18:33 PDT Date: Wed, 07 May 1997 09:18:33 -0700 (PDT) From: holsinal@plu.edu To: Organic Chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Whats the deal with the Mid-semester check on the lab notebooks, did I just miss it or what? From rorabajh@plu.edu Wed May 7 11:25:05 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 LAA17855 for ; Wed, 7 May 1997 11:25:05 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIL4AXD4JA00ET9M@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 7 May 1997 11:21:11 PDT Date: Wed, 07 May 1997 11:21:11 -0700 (PDT) From: rorabajh@plu.edu Subject: the lab final To: The Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII could someone remind me what the format is for the lab final? From rorabajh@plu.edu Wed May 7 11:25:48 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 LAA17888 for ; Wed, 7 May 1997 11:25:48 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIL4BQD2GC00ET9M@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 7 May 1997 11:21:50 PDT Date: Wed, 07 May 1997 11:21:50 -0700 (PDT) From: rorabajh@plu.edu Subject: Re: your mail In-reply-to: To: holsinal@plu.edu Cc: Organic Chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII i think that we turn our notebooks in by next friday, i don't remember ever hearing of a mid-semester check: just turning them in. On Wed, 7 May 1997 holsinal@plu.edu wrote: > Whats the deal with the Mid-semester check on the lab notebooks, did I > just miss it or what? > > From petershm@plu.edu Wed May 7 11:48:54 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 LAA18117 for ; Wed, 7 May 1997 11:48:53 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIL54FT76K00DV9P@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 7 May 1997 11:45:00 PDT Date: Wed, 07 May 1997 11:44:59 -0700 (PDT) From: petershm@plu.edu Subject: Re: your mail In-reply-to: To: holsinal@plu.edu Cc: Organic Chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Yea, I never heard anything about it either. I thought maybe we just turned in our books at the end of the semester. ~HP On Wed, 7 May 1997 holsinal@plu.edu wrote: > Whats the deal with the Mid-semester check on the lab notebooks, did I > just miss it or what? > > From smithtw@plu.edu Wed May 7 11:56:01 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 LAA18219 for ; Wed, 7 May 1997 11:56:01 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIL5DAHTTS00D4IA@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 7 May 1997 11:52:09 PDT Date: Wed, 07 May 1997 11:52:07 -0700 (PDT) From: smithtw@plu.edu Subject: Re: the lab final 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 I've heard that it can (and just may) cover all topics covered throughout our various labs. Including techniques and applications of formulas, such as calculating the Rf values asked for on the TLC lab. I guess going over all the labs and their techniques would be the plan for study. Anybody else? On Wed, 7 May 1997 rorabajh@plu.edu wrote: > > could someone remind me what the format is for the lab final? > > From raquetce@plu.edu Wed May 7 12:31:52 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 MAA18493 for ; Wed, 7 May 1997 12:31:52 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIL6MQR6KG00DXN0@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 7 May 1997 12:28:00 PDT Date: Wed, 07 May 1997 12:27:59 -0700 (PDT) From: raquetce@plu.edu Subject: lab notebook To: org chem list Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I know that the syllabus mentioned having the notebook check in the middle of the semester, but I don't remember him ever collecting it so I would assume that we will be turning it in next week. We do have a lab final so I don't think he will be collecting it until after then. By the way, does anyone know when the lab final is? Thank you. From smithtw@plu.edu Wed May 7 12:34:45 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 MAA18566 for ; Wed, 7 May 1997 12:34:45 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIL6Q4DA8G00DVWB@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 7 May 1997 12:30:47 PDT Date: Wed, 07 May 1997 12:30:43 -0700 (PDT) From: smithtw@plu.edu Subject: Re: lab notebook 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've heard that the lab final is given anytime during dead week. We just go in on our own time and take the final while the on-duty prof is there to oversee the test. On Wed, 7 May 1997 raquetce@plu.edu wrote: > > I know that the syllabus mentioned having the notebook check in the middle > of the semester, but I don't remember him ever collecting it so I would > assume that we will be turning it in next week. We do have a lab final so > I don't think he will be collecting it until after then. By the way, does > anyone know when the lab final is? Thank you. > > From mistkaam@plu.edu Wed May 7 12:59:20 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 MAA18727 for ; Wed, 7 May 1997 12:59:19 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIL7KEZZEO00ENWF@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 7 May 1997 12:55:10 PDT Date: Wed, 07 May 1997 12:55:08 -0700 (PDT) From: mistkaam@plu.edu Subject: Re: this weeks lab In-reply-to: To: hoffmasb@plu.edu Cc: organic chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I believe that it is due Monday, like all of the others. On Tue, 6 May 1997 hoffmasb@plu.edu wrote: > > Is this lab due this Friday night, or is it due next Monday like the > others in the past? > Sara > > From balaislv@plu.edu Wed May 7 14:50:50 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 OAA19407 for ; Wed, 7 May 1997 14:50:50 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IILBGXAQMM00DVW1@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 7 May 1997 14:46:51 PDT Date: Wed, 07 May 1997 14:46:50 -0700 (PDT) From: "L.B." Subject: Re: your mail In-reply-to: To: holsinal@plu.edu Cc: Organic Chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Yes, the final will be comprehensive, covering everything we learned for the whole year. Leilani *~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~* ~ ~ * Pacific Lutheran University * ~ E-mail Address: balaislv@plu.edu ~ * (206) 535-7718 * ~ ~ *~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~* On Wed, 7 May 1997 holsinal@plu.edu wrote: > I was wondering is the final going to be comprehensive? > > From taylormr@plu.edu Wed May 7 15:01:59 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 PAA19516 for ; Wed, 7 May 1997 15:01:58 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IILBUMU4Y800E6OF@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 7 May 1997 14:57:55 PDT Date: Wed, 07 May 1997 14:57:54 -0700 (PDT) From: "M.Taylor" Subject: Re: lab notebook In-reply-to: To: raquetce@plu.edu Cc: org chem list Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The lab final is another open lab that takes place between May 12-16. Hope this helps. Michele On Wed, 7 May 1997 raquetce@plu.edu wrote: > > I know that the syllabus mentioned having the notebook check in the middle > of the semester, but I don't remember him ever collecting it so I would > assume that we will be turning it in next week. We do have a lab final so > I don't think he will be collecting it until after then. By the way, does > anyone know when the lab final is? Thank you. > > From guestrp@plu.edu Wed May 7 17:11:26 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 RAA20742 for ; Wed, 7 May 1997 17:11:25 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IILGE73I5C00EEME@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 7 May 1997 17:07:26 PDT Date: Wed, 07 May 1997 17:07:25 -0700 (PDT) From: guestrp@plu.edu Subject: Re: your mail In-reply-to: To: holsinal@plu.edu Cc: Organic Chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The final will be comprehensive. I don't know as to whether it is a standardized exam or one Fryhle writes himself. From guestrp@plu.edu Wed May 7 17:12:35 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 RAA20779 for ; Wed, 7 May 1997 17:12:34 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IILGFG8W0800EEME@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 7 May 1997 17:08:27 PDT Date: Wed, 07 May 1997 17:08:26 -0700 (PDT) From: guestrp@plu.edu Subject: Re: your mail In-reply-to: To: holsinal@plu.edu Cc: Organic Chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII There was not a mid-semester lab notebook check. The lab notebooks will be turned in at the end of the semester sometime. From hiattzr@plu.edu Wed May 7 17:40:18 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 RAA21025 for ; Wed, 7 May 1997 17:40:17 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IILHE2S5MO00EMEA@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 7 May 1997 17:36:23 PDT Date: Wed, 07 May 1997 17:36:21 -0700 (PDT) From: hiattzr@plu.edu Subject: Re: Williamson Synthesis In-reply-to: <01IIKV2MZNWI00D214@plu.edu> To: FAT-N-SASSY Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I'm not looking in the answer book right now, but my guess is that an elimination occured because of steric hindrance of the tert-Butyl substrate. Since the alkoxide was unable to attack the tertiary carbon (due to steric hindrance), it just removed a H from one of the methyl groups and an elimination occured. Ethers are most easily formed in a Williamson synthesis when the substrate is primary with respect to the leaving group. I hope this helps. Zach On Wed, 7 May 1997, FAT-N-SASSY wrote: > In the answer book, question 42 b, a reaction is shown where a williamson > synthesis performed on tert-Butyl bromide yields an alkene. I thought > Williamson syntheses were supposed to create ethers... ??? > > Does anyone know how this happens? > > -Leslie > From 107744.2473@compuserve.com Wed May 7 20:29:28 1997 Received: from hil-img-8.compuserve.com (hil-img-8.compuserve.com [149.174.177.138]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id UAA21920 for ; Wed, 7 May 1997 20:29:27 -0700 Received: by hil-img-8.compuserve.com (8.6.10/5.950515) id XAA07149; Wed, 7 May 1997 23:25:35 -0400 Date: Wed, 7 May 1997 23:25:12 -0400 From: "howard r. kletke" <107744.2473@compuserve.com> Subject: Lab To: unknown Message-ID: <199705072325_MC2-1630-6B0@compuserve.com> In this week's lab there is a suggested stopping point, but is it necessary? Will the crystals be dry enough to continue without the "overnight drying"? Thankyou, Monica From schelvac@plu.edu Wed May 7 20:31:09 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 UAA21974 for ; Wed, 7 May 1997 20:31:08 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IILNCZB1NO00ELAH@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 7 May 1997 20:27:16 PDT Date: Wed, 07 May 1997 20:27:16 -0700 (PDT) From: schelvac@plu.edu Subject: Synthesis of alcohols To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII How does one tell when to use the oxymercuration-demercuration method or the hydroboration-oxidation method when synthesizing alcohols from alkenes? Any information would be helpful. Thanks! From erickstd@plu.edu Wed May 7 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 UAA22143 for ; Wed, 7 May 1997 20:52:15 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IILO40MBTC00EEGU@plu.edu> for organic1@rainier.chem.plu.edu; Wed, 7 May 1997 20:48:20 PDT Date: Wed, 07 May 1997 20:48:18 -0700 (PDT) From: THE PENGUIN Subject: Re: Synthesis of alcohols In-reply-to: To: schelvac@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII You use hydrobromation-oxidation to create an anti-Markovnikov addition of water. The Oxymercuration-Demurcuration adds the -OH and -H in a Markovnikov addition. Hope that helps and i hope i'm right. -TDE On Wed, 7 May 1997 schelvac@plu.edu wrote: > How does one tell when to use the oxymercuration-demercuration method or > the hydroboration-oxidation method when synthesizing alcohols from > alkenes? Any information would be helpful. > > Thanks! > > From 107744.2473@compuserve.com Wed May 7 22:19:35 1997 Received: from dub-img-9.compuserve.com (dub-img-9.compuserve.com [149.174.206.139]) by rainier.chem.plu.edu (950413.SGI.8.6.12/950213.SGI.AUTOCF) via ESMTP id WAA22633 for ; Wed, 7 May 1997 22:19:34 -0700 Received: by dub-img-9.compuserve.com (8.6.10/5.950515) id BAA05040; Thu, 8 May 1997 01:15:42 -0400 Date: Thu, 8 May 1997 01:15:25 -0400 From: "howard r. kletke" <107744.2473@compuserve.com> Subject: final To: unknown Message-ID: <199705080115_MC2-1631-C606@compuserve.com> I WAS WONDERING IF ANYONE KNEW AT WHAT TIME THE FINAL WAS? THANKS, MONICA From fryhle@u.washington.edu Wed May 7 22:25:57 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 WAA22681 for ; Wed, 7 May 1997 22:25:56 -0700 Received: from homer37.u.washington.edu (fryhle@homer37.u.washington.edu [140.142.16.3]) by jason05.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with ESMTP id WAA22000 for ; Wed, 7 May 1997 22:22:05 -0700 Received: from localhost (fryhle@localhost) by homer37.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with SMTP id WAA83744 for ; Wed, 7 May 1997 22:22:04 -0700 Date: Wed, 7 May 1997 22:22:04 -0700 (PDT) From: Craig Fryhle To: Organic Chemistry I List Subject: Culminating Activities Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings, everyone. Here are the answers to some of your recent questions. The final exam is comprehensive, and will include material from Chapter 11. The final is an exam of the same format as the other three you have taken so far. Some multiple choice, some written. During the last week of lab (next week) you will take the Lab Final Exam. It will be administered in the Open Lab by the faculty teaching out there. You'll have a set time (probably one hour) to do it, although you may start anytime that allows you at least one hour before closing time. You will sign out and exam from the professor, noting the time. You will turn it in to her/him and the time will be recoreded. The exam will be closed book. the exam will cover practical things about the work you have done. It will check to see if you understand what you did or why you did it, and query why various lab manipulations are used to do what they do. I hope that answers most of your questions. 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 blackkl@plu.edu Wed May 7 22:26:26 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 WAA22688 for ; Wed, 7 May 1997 22:26:24 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IILRD0XXJG00ES6U@plu.edu> for Organic1@rainier.chem.plu.edu; Wed, 7 May 1997 22:21:57 PDT Date: Wed, 07 May 1997 22:21:52 -0700 (PDT) From: blackkl@plu.edu Subject: Re: final In-reply-to: <199705080115_MC2-1631-C606@compuserve.com> To: "howard r. kletke" <107744.2473@compuserve.com> Cc: unknown Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The final for Organic Chemistry is Monday the 19th at 8:00 am until 9:50 am, I hope that answers your question! On Thu, 8 May 1997, howard r. kletke wrote: > I WAS WONDERING IF ANYONE KNEW AT WHAT TIME THE FINAL WAS? THANKS, MONICA > From fryhle@u.washington.edu Wed May 7 22:30:21 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 WAA22761 for ; Wed, 7 May 1997 22:30:20 -0700 Received: from homer37.u.washington.edu (fryhle@homer37.u.washington.edu [140.142.16.3]) by jason02.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with ESMTP id WAA18876 for ; Wed, 7 May 1997 22:26:29 -0700 Received: from localhost (fryhle@localhost) by homer37.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with SMTP id WAA126938 for ; Wed, 7 May 1997 22:26:29 -0700 Date: Wed, 7 May 1997 22:26:29 -0700 (PDT) From: Craig Fryhle To: Organic Chemistry I List Subject: Lab Notebooks Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Hello again. I forgot to mention that, as per the syllabus, lab notebooks are due to be turned in at the stockroom by the close of lab next Friday. 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 May 7 22:35:52 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 WAA22824 for ; Wed, 7 May 1997 22:35:51 -0700 Received: from homer37.u.washington.edu (fryhle@homer37.u.washington.edu [140.142.16.3]) by jason05.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with ESMTP id WAA10644; Wed, 7 May 1997 22:32:00 -0700 Received: from localhost (fryhle@localhost) by homer37.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with SMTP id WAA100680; Wed, 7 May 1997 22:32:00 -0700 Date: Wed, 7 May 1997 22:32:00 -0700 (PDT) From: Craig Fryhle To: FAT-N-SASSY cc: organic1 Subject: Re: Williamson Synthesis In-Reply-To: <01IIKV2MZNWI00D214@plu.edu> Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings, Leslie, et al. A Williamson ether synthesis is the name given to a reaction between an alkoxide nucleophile and a compound with a leaving group, where the specific structures are such that an SN2 mechanism can occur to form an ether. Although the reagents in 10.42b are of the type mentioned above, the specific reactants lead to products by an E2 mechanism, rather than SN2, since the compound with the leaving group is sterically hindered (a tertiary alkyl halike). Whether SN2 or E2 occurs when an alkoxide nucleophile/base is used strongly dependent on the structure of the compound with the leaving group. CBF On Wed, 7 May 1997, FAT-N-SASSY wrote: > In the answer book, question 42 b, a reaction is shown where a williamson > synthesis performed on tert-Butyl bromide yields an alkene. I thought > Williamson syntheses were supposed to create ethers... ??? > > Does anyone know how this happens? > > -Leslie > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 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 harriscr@plu.edu Thu May 8 00:23:43 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 AAA23714 for ; Thu, 8 May 1997 00:23:42 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IILVH7JSJQ00F44Y@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 8 May 1997 00:19:45 PDT Date: Thu, 08 May 1997 00:19:44 -0700 (PDT) From: harriscr@plu.edu Subject: Re: the lab final In-reply-to: To: smithtw@plu.edu Cc: rorabajh@plu.edu, The Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I also heard the the lab final will cover thing like reactions along with the other stuff that was already talked about. -clayton On Wed, 7 May 1997 smithtw@plu.edu wrote: > I've heard that it can (and just may) cover all topics covered throughout > our various labs. Including techniques and applications of formulas, such > as calculating the Rf values asked for on the TLC lab. I guess going over > all the labs and their techniques would be the plan for study. > Anybody else? > > > On Wed, 7 May 1997 rorabajh@plu.edu wrote: > > > > > could someone remind me what the format is for the lab final? > > > > > > From fryhle@u.washington.edu Thu May 8 08:40:59 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 IAA26089 for ; Thu, 8 May 1997 08:40:58 -0700 Received: from homer16.u.washington.edu (fryhle@homer16.u.washington.edu [140.142.70.17]) by jason05.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with ESMTP id IAA16424 for ; Thu, 8 May 1997 08:37:07 -0700 Received: from localhost (fryhle@localhost) by homer16.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with SMTP id IAA109828 for ; Thu, 8 May 1997 08:37:06 -0700 Date: Thu, 8 May 1997 08:37:06 -0700 (PDT) From: Craig Fryhle To: Organic Chemistry I List Subject: Organic Special Projects Lab Overview Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings, everyone. On Friday I will bring application forms to class for the Organic Special Projects Lab. I'll also post some outside my office door Thursday Afternoon. I'll describe the course in class on Friday. I've also copied below a bit of the description for the course from the application form. I encourage you to apply. Check with me if you have any questions. Applications are due back to me next Wednesday. ORGANIC SPECIAL PROJECTS LABORATORY - Chemistry 336 OVERVIEW The Organic Special Projects Lab (Chem 336) is an alternative to the regular second term organic lab course (Chem 334). The course is limited to a small number of students who are selected from among those that apply using the application form below. All students taking second term organic lab register for the regular lab (Chem 334). If they are accepted to the Special Projects Lab their registration is changed to Chem 336 by the instructor. The Organic Special Projects Lab has a scheduled lab period on Friday afternoon. It is occasionally necessary for participants to work during other Open Lab hours, as well. Students selected for the Organic Special Projects Laboratory undertake a set of four multi-week projects that, except for the first one, are entirely different from those of their peers. Significant independence and self-motivation is required. While the first project will be identical for all students, it is designed so as to acquaint you with hands-on use of our FTNMR, IR, GCMS and other spectroscopic techniques and equipment available in the department. Beginning with the second project, each student will embark on their own journey. The second project will likely involve a multistep synthesis, and might contribute to an ongoing research project. The third project will be a reaction which gives an "unknown" product. In this project you will utilize your general background in organic reactions and mechanisms along with spectroscopic tools to identify the "unknown" product formed. The fourth project, which could be begun concurrently with other work, may be an exercise in molecular modeling. Throughout the semester reaction products are to be fully characterized by appropriate spectroscopic methods and useful physical constants. All projects are to be thoroughly documented in the lab notebook. The lab notebook will be turned in for grading periodically throughout the semester. A typed formal report in the format of a paper in the Journal of Organic Chemistry (with a graded draft) will be written on the second project of the semester. A sample paper from the Journal of Organic Chemistry will be provided for your review. Your work on the fourth project will involve a presentation to the class. At the end of the semester a mini-symposium will be held at which you will be able to present your third project work to the class and other students. Our class symposium will be combined with the Division of Natural Sciences' "Academic Festival" symposium. Your presentations may take the format of either a brief oral presentation or a poster. ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 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 Thu May 8 08:43:31 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 IAA26157 for ; Thu, 8 May 1997 08:43:30 -0700 Received: from homer16.u.washington.edu (fryhle@homer16.u.washington.edu [140.142.70.17]) by jason01.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with ESMTP id IAA21458 for ; Thu, 8 May 1997 08:39:38 -0700 Received: from localhost (fryhle@localhost) by homer16.u.washington.edu (8.8.4+UW97.04/8.8.4+UW97.04) with SMTP id IAA111754 for ; Thu, 8 May 1997 08:39:37 -0700 Date: Thu, 8 May 1997 08:39:37 -0700 (PDT) From: Craig Fryhle To: Organic Chemistry I List Subject: Learning Group Problem - Chapter 11 Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings, I will have copies of the Chapter 11 Learning Group problem outside my door on Thursday afternoon. I'll also bring some to class on Friday. There are some structures, so I can't post it by email. 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 mistkaam@plu.edu Thu May 8 11:47:39 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 LAA27312 for ; Thu, 8 May 1997 11:47:38 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIMJD7G2MO00ESGH@plu.edu> for Organic1@rainier.chem.plu.edu; Thu, 8 May 1997 11:43:43 PDT Date: Thu, 08 May 1997 11:43:42 -0700 (PDT) From: mistkaam@plu.edu Subject: Re: Lab In-reply-to: <199705072325_MC2-1630-6B0@compuserve.com> To: "howard r. kletke" <107744.2473@compuserve.com> Cc: unknown Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I think that it is necessary to let the crystals dry overnight. The lab book says, "Allow the crystals to dry throughly at room temperature at least overnight." On Wed, 7 May 1997, howard r. kletke wrote: > In this week's lab there is a suggested stopping point, but is it > necessary? Will the crystals be dry enough to continue without the > "overnight drying"? Thankyou, Monica > From mistkaam@plu.edu Thu May 8 11:50:07 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 LAA27341 for ; Thu, 8 May 1997 11:50:07 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIMJFQ0HL400ESGH@plu.edu> for Organic1@rainier.chem.plu.edu; Thu, 8 May 1997 11:45:46 PDT Date: Thu, 08 May 1997 11:45:44 -0700 (PDT) From: mistkaam@plu.edu Subject: Re: final In-reply-to: <199705080115_MC2-1631-C606@compuserve.com> To: "howard r. kletke" <107744.2473@compuserve.com> Cc: unknown Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The final is on Moday the 19th ath 8:00 am. unless Fryhle starts it at 7:30 like our other exams. On Thu, 8 May 1997, howard r. kletke wrote: > I WAS WONDERING IF ANYONE KNEW AT WHAT TIME THE FINAL WAS? THANKS, MONICA > From youngcf@plu.edu Thu May 8 12:32:41 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 MAA27643 for ; Thu, 8 May 1997 12:32:40 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIMKY0H3WW00ED76@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 8 May 1997 12:28:45 PDT Date: Thu, 08 May 1997 12:28:43 -0700 (PDT) From: youngcf@plu.edu Subject: Re: Synthesis of alcohols In-reply-to: To: schelvac@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The oxymercuration-demercuration method is used when the synthesis follows the Markovnicov's rule. I think it is the addition of the mercury group to the most hydrogen substituted group of a double bond. The alcohol is attached to the less hydrogen substituted carbon of the double bond. The mercury group is then replaced by a -H atom in the second part of the synthesis. The hydroboration-oxidation is used for anti-markovnicov addition of an alcohol. Simply just the opposite of the above. In this addition, there is no need for hydrogen and methyl rearrangements. Look in your book for further examples. Hope this helps Curtis On Wed, 7 May 1997 schelvac@plu.edu wrote: > How does one tell when to use the oxymercuration-demercuration method or > the hydroboration-oxidation method when synthesizing alcohols from > alkenes? Any information would be helpful. > > Thanks! > > From taylormr@plu.edu Thu May 8 14:33:16 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 OAA28330 for ; Thu, 8 May 1997 14:33:16 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIMP5KCPHS00E8CI@plu.edu> for Organic1@rainier.chem.plu.edu; Thu, 8 May 1997 14:29:21 PDT Date: Thu, 08 May 1997 14:29:20 -0700 (PDT) From: "M.Taylor" Subject: Re: final In-reply-to: <199705080115_MC2-1631-C606@compuserve.com> To: "howard r. kletke" <107744.2473@compuserve.com> Cc: unknown Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The final is on May 19, 8:00 am - 9:50. michlele On Thu, 8 May 1997, howard r. kletke wrote: > I WAS WONDERING IF ANYONE KNEW AT WHAT TIME THE FINAL WAS? THANKS, MONICA > From christja@plu.edu Thu May 8 15:04:34 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 PAA28560 for ; Thu, 8 May 1997 15:04:34 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIMQ9COXRK00EKL0@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 8 May 1997 15:00:39 PDT Date: Thu, 08 May 1997 15:00:38 -0700 (PDT) From: mirror man Subject: Re: the lab final In-reply-to: To: harriscr@plu.edu Cc: The Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII will the lab final cover specific results recovered for labs or just the techniques for obtaining the results? jz From buchanbr@plu.edu Thu May 8 15:42:29 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 PAA28836 for ; Thu, 8 May 1997 15:42:28 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIMRKATQV400EZYD@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 8 May 1997 15:38:30 PDT Date: Thu, 08 May 1997 15:38:30 -0700 (PDT) From: Brook Buchanan Subject: Lab Final To: Organic Chemlist Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Does anyone know if the lab final will require us to demonstrate certain techniques as well as a written part? B From boothcj@plu.edu Thu May 8 16:05:08 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 QAA29020 for ; Thu, 8 May 1997 16:05:07 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIMSD9481C00ENRL@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 8 May 1997 16:01:06 PDT Date: Thu, 08 May 1997 16:01:03 -0700 (PDT) From: boothcj@plu.edu Subject: Re: Lab Final In-reply-to: To: Brook Buchanan Cc: Organic Chemlist Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII i think the lab final is pretty much open to anything we have covered in the labs we did this semester. it would be my guess that there would be some written, and i'm pretty sure there will be some techniques we have to cover. GOOD LUCK EVERYONE On Thu, 8 May 1997, Brook Buchanan wrote: > Does anyone know if the lab final will require us to demonstrate certain > techniques as well as a written part? > > B > > From boothcj@plu.edu Thu May 8 16:20:31 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 QAA29148 for ; Thu, 8 May 1997 16:20:30 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIMSWEHM3400E0DR@plu.edu> for ORGANIC1@RAINIER.CHEM.PLU.EDU; Thu, 8 May 1997 16:16:32 PDT Date: Thu, 08 May 1997 16:16:31 -0700 (PDT) From: boothcj@plu.edu Subject: BENZOIC LAB To: ORGANIC1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII PROF. FRYHLE i know it is my own fault for not doing lab early, but myself and many others chose not to. the lab room was full of people trying to get it done and i was one of them. there were so many of us that the stockroom ran out of buckets for us, so i had to be put on a waiting list. i went to do lab at about 2 and i figured i would get most of it dome today. it turns out that i probably won't get a bucket until 5 or later. the prob. is i have a class tomorrow during the lab time, so i will only about an hour to finish what i don't get done today. I (and maybe many others) have a request that the lab be due on Wednesday instead of Monday so we can have Tuesday to do what we don't get done this week. Very sincerely, All of us that need the time From christja@plu.edu Thu May 8 16:22:26 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 QAA29186 for ; Thu, 8 May 1997 16:22:25 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIMSYS593K00EVTF@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 8 May 1997 16:18:25 PDT Date: Thu, 08 May 1997 16:18:24 -0700 (PDT) From: mirror man Subject: Re: Lab Final In-reply-to: To: Brook Buchanan Cc: Organic Chemlist Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII the lab final will most likely be only written. because of the number of students that must take the exam i don't think any hands on use of techniques will be done. jz On Thu, 8 May 1997, Brook Buchanan wrote: > Does anyone know if the lab final will require us to demonstrate certain > techniques as well as a written part? > > B > > From christja@plu.edu Thu May 8 16:24:51 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 QAA29258 for ; Thu, 8 May 1997 16:24:50 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIMT1WBN2000EVTF@plu.edu> for ORGANIC1@rainier.chem.plu.edu; Thu, 8 May 1997 16:20:55 PDT Date: Thu, 08 May 1997 16:20:55 -0700 (PDT) From: mirror man Subject: magnesium In-reply-to: To: boothcj@plu.edu Cc: ORGANIC1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII just a general questioin: does anyone know why magnesium is the only metal used for organic synthesis? is it just the best metal to react so the other metals out there are just not mentioned? jz From christja@plu.edu Thu May 8 16:30:18 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 QAA29349 for ; Thu, 8 May 1997 16:30:17 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIMT8ID2JK00EVTF@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 8 May 1997 16:26:16 PDT Date: Thu, 08 May 1997 16:26:15 -0700 (PDT) From: mirror man Subject: lab notebooks In-reply-to: Cc: Organic Chemlist Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII in our notebooks we are required to have an abbreviatioins section and a common msds section. i am not a big fan of abreviations so i haven't put anything in that section of my notebook. will my grade by affected for not using this section of my notebook? jz From erickstd@plu.edu Thu May 8 16:33:33 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 QAA29411 for ; Thu, 8 May 1997 16:33:32 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIMTCL81Q800FAKS@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 8 May 1997 16:29:33 PDT Date: Thu, 08 May 1997 16:29:33 -0700 (PDT) From: THE PENGUIN Subject: Wait? To: O-Chem List Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII hey y'all, if we stop the lab at the space it suggests(not at the drying of the crystals), do we have to wait for a basket or can we just add the stuff and work like that? timmy ps-Raisins-smuggle more!! XXXX X XXX/ XXXXXX\ XXXX XXXXX# X**XX### X***X##### X***X##### X**XX##### *XXXX### XXXXXX ^^^^^^^^^ Dooby Dooby Doo!! From triplema@plu.edu Thu May 8 16:45:23 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 QAA29521 for ; Thu, 8 May 1997 16:45:23 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIMTREWF9C00E7WC@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 8 May 1997 16:41:29 PDT Date: Thu, 08 May 1997 16:41:29 -0700 (PDT) From: Harvey the Wonder Hamster Subject: lab 25B To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Hi. A little word of advice. Make sure you label your beaker before you nuke it in the oven. I didn't and it got jacked by someone. I know you probably have already done this part of the lab by now, but you never know the heapless pleasure that this advice could provide you in the future. Happy lab-doing. From balaislv@plu.edu Thu May 8 17:03:31 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 RAA29660 for ; Thu, 8 May 1997 17:03:30 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIMUESL1AO00F63J@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 8 May 1997 16:59:34 PDT Date: Thu, 08 May 1997 16:59:33 -0700 (PDT) From: "L.B." Subject: Re: Lab Final In-reply-to: To: Brook Buchanan Cc: Organic Chemlist Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The lab final wil be nothing but a written exam covering important CONCEPTS you learned from your labs. Leilani *~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~* ~ ~ * Pacific Lutheran University * ~ E-mail Address: balaislv@plu.edu ~ * (206) 535-7718 * ~ ~ *~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~* On Thu, 8 May 1997, Brook Buchanan wrote: > Does anyone know if the lab final will require us to demonstrate certain > techniques as well as a written part? > > B > > From vogega@plu.edu Thu May 8 18:53:25 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 SAA02415 for ; Thu, 8 May 1997 18:53:24 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIMY9460A800FIMR@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 8 May 1997 18:49:31 PDT Date: Thu, 08 May 1997 18:49:31 -0700 (PDT) From: vogega@plu.edu Subject: lab To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII hey everyone- this is for anyone that hasn't done their lab, or is doing it again. i have had to do it twice so i have some suggestions. cut your magnesium into tiny pieces-they will disolve quicker. when you get ready for the dry ice, weigh it in the little beaker, covered with a watch glass. the first time i didn't cover the beaker and the dry ice apparently absorbed a lot of water from the atmosphere. the result was that i didn't get any crystals and had to repeat the experiment. also when you are pipeting the reagent into the beaker with the dry ice, beware of how you are holding the pipette. i had mine sideways to keep it from leaking before i placed it in the beaker. the diethyl ether has a high vapor pressure and i lost three fourths of my product because it came shooting out of the pipette, even though it was sideways and i didn't squeeze the bulb. i hope these hints will help any of you that haven't done the lab. hopefully you will get results the first time around. g. voge From crouthmr@plu.edu Thu May 8 21:00:42 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 VAA03199 for ; Thu, 8 May 1997 21:00:42 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIN2OWM3SG00FJZ5@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 8 May 1997 20:56:46 PDT Date: Thu, 08 May 1997 20:56:46 -0700 (PDT) From: Sourcrout Subject: Formal Reports To: Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Anyone know when we should expect our formal reports back? MRC From harriscr@plu.edu Thu May 8 21:55:31 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 VAA03571 for ; Thu, 8 May 1997 21:55:30 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIN4LJYF5C00FWIP@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 8 May 1997 21:51:21 PDT Date: Thu, 08 May 1997 21:51:21 -0700 (PDT) From: harriscr@plu.edu Subject: Lab final To: Organic chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Does anyone know if an example of the lab final will be posted, just like how an example of our tests are posted? -Clayton From balaislv@plu.edu Fri May 9 00:03:04 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 AAA06550 for ; Fri, 9 May 1997 00:03:03 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIN91WQ50000FX4U@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 8 May 1997 23:59:05 PDT Date: Thu, 08 May 1997 23:59:03 -0700 (PDT) From: "L.B." Subject: Re: Lab final In-reply-to: To: harriscr@plu.edu Cc: Organic chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII There will not be an example of the lab final posted like our regular exams. You're suppose to rely on your knowledge of what you learned from your lab text and from doing the labs. In fact, it's sort of a hush-hush thing. After you take the lab final, you're not supposed to tell anyone about what was on it. No hints or clues at all. You can pretty much tell others if you thought it was a hard final or not and how you thought you did on it, but you can't explain yourself. Hope you (and everyone else) do well on it. Leilani *~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~* ~ ~ * Pacific Lutheran University * ~ E-mail Address: balaislv@plu.edu ~ * (206) 535-7718 * ~ ~ *~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~* On Thu, 8 May 1997 harriscr@plu.edu wrote: > > > Does anyone know if an example of the lab final will be posted, just like > how an example of our tests are posted? > > -Clayton > > From craigtm@plu.edu Fri May 9 07:47:12 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 HAA13204 for ; Fri, 9 May 1997 07:47:11 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IINP9DX91C00FFM3@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 9 May 1997 07:43:14 PDT Date: Fri, 09 May 1997 07:43:13 -0700 (PDT) From: craigtm@plu.edu Subject: Re: Lab Final In-reply-to: To: Brook Buchanan Cc: Organic Chemlist Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I believe the lab final is only written considering that we only have one hour to complete it. Tiffany On Thu, 8 May 1997, Brook Buchanan wrote: > Does anyone know if the lab final will require us to demonstrate certain > techniques as well as a written part? > > B > > From crouthmr@plu.edu Fri May 9 09:02:04 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 JAA13794 for ; Fri, 9 May 1997 09:02:03 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IINRVBDCS600FOGT@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 9 May 1997 08:58:09 PDT Date: Fri, 09 May 1997 08:58:09 -0700 (PDT) From: Sourcrout Subject: LG 11 To: Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The quiz is on Monday so is the LG prez on Wednesday or Friday? And what's goin on the other day? MC From taylormr@plu.edu Fri May 9 10:29:56 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 KAA14341 for ; Fri, 9 May 1997 10:29:55 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IINUY47C4G00ETMG@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 9 May 1997 10:25:58 PDT Date: Fri, 09 May 1997 10:25:56 -0700 (PDT) From: "M.Taylor" Subject: Re: LG 11 In-reply-to: To: Sourcrout Cc: Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The learning group presentations will still propably be on wednesday and hopefully on friday, Dr. Fryhle will use that as a review day for the final. Also, we still have to fill out the class evaluations so he might have us do those on friday also. hope this helps. michele On Fri, 9 May 1997, Sourcrout wrote: > The quiz is on Monday so is the LG prez on Wednesday or Friday? And what's > goin on the other day? > MC > > From gigraykc@plu.edu Fri May 9 10:33:40 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 KAA14417 for ; Fri, 9 May 1997 10:33:39 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IINV2E2TLC00FX2A@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 9 May 1997 10:29:27 PDT Date: Fri, 09 May 1997 10:29:23 -0700 (PDT) From: gigraykc@plu.edu Subject: Re: the lab final In-reply-to: To: mirror man Cc: harriscr@plu.edu, The Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII The lab final will just cover the techniques used for obtaining the results and how to do any of the calculations. kelli On Thu, 8 May 1997, mirror man wrote: > > > > will the lab final cover specific results recovered for labs or just the > techniques for obtaining the results? > > jz > > > > From gigraykc@plu.edu Fri May 9 10:38:30 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 KAA14488 for ; Fri, 9 May 1997 10:38:29 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IINV8MO4M000FX2A@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 9 May 1997 10:34:27 PDT Date: Fri, 09 May 1997 10:34:25 -0700 (PDT) From: gigraykc@plu.edu Subject: Re: LG 11 In-reply-to: To: Sourcrout Cc: Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Since the quiz is on Monday and the LG prez. is on Wednesday I would assume that friday is used as a review day for the final.-kelli On Fri, 9 May 1997, Sourcrout wrote: > The quiz is on Monday so is the LG prez on Wednesday or Friday? And what's > goin on the other day? > MC > > From balaislv@plu.edu Fri May 9 11:20:47 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 LAA14756 for ; Fri, 9 May 1997 11:20:46 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IINWQ5UECW00E5XM@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 9 May 1997 11:16:48 PDT Date: Fri, 09 May 1997 11:16:47 -0700 (PDT) From: "L.B." Subject: Re: LG 11 In-reply-to: To: Sourcrout Cc: Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Since the quiz will be on Monday, LG presentations will be on Wednesday. Firday will be REVIEW day for finals the following Monday. Leilani *~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~* ~ ~ * Pacific Lutheran University * ~ E-mail Address: balaislv@plu.edu ~ * (206) 535-7718 * ~ ~ *~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~* On Fri, 9 May 1997, Sourcrout wrote: > The quiz is on Monday so is the LG prez on Wednesday or Friday? And what's > goin on the other day? > MC > > From hardinkm@plu.edu Fri May 9 12:51:47 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 MAA15322 for ; Fri, 9 May 1997 12:51:46 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IINZW3149S003A82@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 9 May 1997 12:47:51 PDT Date: Fri, 09 May 1997 12:47:51 -0700 (PDT) From: cancel To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII To Dr. Fryele or anyone who knows--- Are our grades up to right before the final going to be posted before the final sometime? I would kinda like to have an idea of where I stand before I take the final exam. Thanks---- From kamperka@plu.edu Fri May 9 12:57:47 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 MAA15391 for ; Fri, 9 May 1997 12:57:46 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIO04HYGE800FNNQ@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 9 May 1997 12:53:51 PDT Date: Fri, 09 May 1997 12:53:51 -0700 (PDT) From: kamperka@plu.edu Subject: lab final To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I guess I wasn't paying attention in class today, but is the lab final available during the regular lab times, or is it available at any time during the day? Thanks -KK From taylormr@plu.edu Fri May 9 13:28:21 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 NAA15622 for ; Fri, 9 May 1997 13:28:21 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIO16F8QOG00G2P1@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 9 May 1997 13:24:26 PDT Date: Fri, 09 May 1997 13:24:25 -0700 (PDT) From: "M.Taylor" Subject: Re: lab final In-reply-to: To: kamperka@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII since the lab final has to be administered by a lab prof. it can only be offered during regular lab hours. hope this helps. michele On Fri, 9 May 1997 kamperka@plu.edu wrote: > > I guess I wasn't paying attention in class today, but is the lab final > available during the regular lab times, or is it available at any time > during the day? Thanks > > -KK > > From larsenak@plu.edu Fri May 9 14:06:56 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 OAA15897 for ; Fri, 9 May 1997 14:06:55 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIO2J9KMF400FXWG@plu.edu> for Organic1@rainier.chem.plu.edu; Fri, 9 May 1997 14:03:01 PDT Date: Fri, 09 May 1997 14:03:01 -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 Are labs accepted late? From storeyad@plu.edu Fri May 9 14:26:08 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 OAA16056 for ; Fri, 9 May 1997 14:26:07 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIO36UGJ9C00E6E4@plu.edu> for Organic1@rainier.chem.plu.edu; Fri, 9 May 1997 14:22:03 PDT Date: Fri, 09 May 1997 14:22:02 -0700 (PDT) From: madam president Subject: Re: late labs 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 yes, but 10% is taken off for every day that it is late. On Fri, 9 May 1997 larsenak@plu.edu wrote: > Are labs accepted late? > > From balaislv@plu.edu Fri May 9 16:50:28 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 QAA16907 for ; Fri, 9 May 1997 16:50:27 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIO88X6LSG00GCB1@plu.edu> for Organic1@rainier.chem.plu.edu; Fri, 9 May 1997 16:46:29 PDT Date: Fri, 09 May 1997 16:46:29 -0700 (PDT) From: "L.B." 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 Yes, labs are accepted late. They're deducted 10 pts. everyday it's late. After that, you can only get 50% for it. Leilani *~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~* ~ ~ * Pacific Lutheran University * ~ E-mail Address: balaislv@plu.edu ~ * (206) 535-7718 * ~ ~ *~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~*~* On Fri, 9 May 1997 larsenak@plu.edu wrote: > Are labs accepted late? > > From taylormr@plu.edu Fri May 9 19:11:01 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 TAA17691 for ; Fri, 9 May 1997 19:11:00 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIOD57Q2AO00FQIS@plu.edu> for Organic1@rainier.chem.plu.edu; Fri, 9 May 1997 19:07:03 PDT Date: Fri, 09 May 1997 19:07:03 -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 Yes labs are accepted late but every day it is late, 10% of your grade is deducted. The max points off is 50%. hope this helps. michele On Fri, 9 May 1997 larsenak@plu.edu wrote: > Are labs accepted late? > > From hardinkm@plu.edu Fri May 9 20:07:29 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 UAA18026 for ; Fri, 9 May 1997 20:07:28 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIOF49AK5C00C7MF@plu.edu> for Organic1@rainier.chem.plu.edu; Fri, 9 May 1997 20:03:33 PDT Date: Fri, 09 May 1997 20:03:32 -0700 (PDT) From: cancel 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 Yes, they are, because I turned one in late a few weeks ago. You just get a deduction, but it's better than no credit! You would probably want to get it in by Monday though, since that's when our last lab is due. On Fri, 9 May 1997 larsenak@plu.edu wrote: > Are labs accepted late? > > From vogega@plu.edu Sun May 11 10:13:20 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 KAA29375 for ; Sun, 11 May 1997 10:13:19 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIQMYAHGMS00FJNN@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 11 May 1997 10:09:23 PDT Date: Sun, 11 May 1997 10:09:23 -0700 (PDT) From: vogega@plu.edu Subject: group 19 To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII hey group 19- we really need to meet soon to do our last presentation. how about monday night at 7 or so? i think is the only night that i could meet or i could around 8 tonight. let me know as soon as possible. gretchen From bobbtl@plu.edu Sun May 11 20:47:17 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 UAA02498 for ; Sun, 11 May 1997 20:47:17 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIR937LR9C00GJZW@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 11 May 1997 20:43:17 PDT Date: Sun, 11 May 1997 20:43:16 -0700 (PDT) From: bobbtl@plu.edu Subject: Lab 25B To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I was wondering if all of the molar ratios for the Grignard and Benzoic acid reactions are 1:1? If not what are they? From archerka@plu.edu Sun May 11 20:50:45 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 UAA02559 for ; Sun, 11 May 1997 20:50:45 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIR97INDVM00G33O@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 11 May 1997 20:46:46 PDT Date: Sun, 11 May 1997 20:46:45 -0700 (PDT) From: archerka@plu.edu Subject: Grignard Lab To: organic chemistry list Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I'm having trouble with Question #1 on the Grignard Lab. How does benzene form as a side product during the reaction using phenylmagnesium? Thanks -Kristy From bekemj@plu.edu Sun May 11 23:06:00 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 XAA08851 for ; Sun, 11 May 1997 23:05:59 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIRDX8KALC00FTSQ@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 11 May 1997 23:02:01 PDT Date: Sun, 11 May 1997 23:02:01 -0700 (PDT) From: bekemj@plu.edu To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII After the second crystallization in the Grignard synthesis, my crystals would not dry readily. I have left them to dry over the weekend. Is this normal? Mike B. From bekemj@plu.edu Sun May 11 23:10:13 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 XAA08915 for ; Sun, 11 May 1997 23:10:12 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIRE3FGXFQ00FTSQ@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 11 May 1997 23:06:13 PDT Date: Sun, 11 May 1997 23:06:13 -0700 (PDT) From: bekemj@plu.edu To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII What prevents the H from LiAlH4 from reacting with ET O- ? Is it due to relative stability or just the number of Hs attached to the Al? From bekemj@plu.edu Sun May 11 23:12:39 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 XAA08949 for ; Sun, 11 May 1997 23:12:39 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIRE6G9BD800FTSQ@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 11 May 1997 23:08:40 PDT Date: Sun, 11 May 1997 23:08:40 -0700 (PDT) From: bekemj@plu.edu To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII What p[roperties account for LiAlH4 being a strong reducing agent? From bekemj@plu.edu Sun May 11 23:17:13 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 XAA09051 for ; Sun, 11 May 1997 23:17:13 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIREC2F6G200FTSQ@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 11 May 1997 23:13:12 PDT Date: Sun, 11 May 1997 23:13:11 -0700 (PDT) From: bekemj@plu.edu To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII On pg 474, in the reaction of pyridine with CrO3 and HCl, does (in the product) CrO3Cl- form an ionic bond with the N+? Mike B. From rorabajh@plu.edu Mon May 12 11:06:52 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 LAA13038 for ; Mon, 12 May 1997 11:06:52 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIS33Z7V6E00GNJ9@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 12 May 1997 11:02:53 PDT Date: Mon, 12 May 1997 11:02:53 -0700 (PDT) From: rorabajh@plu.edu Subject: the percent yield To: The Organic Journal Club Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII how is the percent yield calculated for this lab? i'm really confused as to which reagents were the contributors to the organic product. From bowersmy@plu.edu Mon May 12 12:57:56 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 MAA13799 for ; Mon, 12 May 1997 12:57:55 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIS6ZMCGIO00GKG3@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 12 May 1997 12:53:55 PDT Date: Mon, 12 May 1997 12:53:54 -0700 (PDT) From: bowersmy@plu.edu Subject: Re: the percent yield 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 calculating the percent yield I used the bromobenzene to calculate the theoretical yield because it was the limiting reagent. I hope that helps. On Mon, 12 May 1997 rorabajh@plu.edu wrote: > how is the percent yield calculated for this lab? i'm really confused as > to which reagents were the contributors to the organic product. > > From crouthmr@plu.edu Mon May 12 13:43:58 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 NAA14228 for ; Mon, 12 May 1997 13:43:57 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIS8LG0SJK00H0ZT@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 12 May 1997 13:39:47 PDT Date: Mon, 12 May 1997 13:39:45 -0700 (PDT) From: Sourcrout Subject: Grignard Lab crystals In-reply-to: To: bekemj@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII My crystals were rather wet too after I Craig-tubed them. Unfortunatly I decided that the text was in charge and I didn't leave them to dry. When I weighed them, I found that I had a 110% recovery (water)! And my MP was about 15 degrees short. What was dumber was that I figured this out after I turned it in for grading. So you should probably leave it for drying if possable. MRC From maschhjt@plu.edu Mon May 12 14:05:12 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 OAA14536 for ; Mon, 12 May 1997 14:05:12 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IIS9C0X3C000GIU2@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 12 May 1997 14:01:11 PDT Date: Mon, 12 May 1997 14:01:10 -0700 (PDT) From: maschhjt@plu.edu Subject: Re: Grignard Lab In-reply-to: To: organic1 , archerka@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Kristy, Look on page 267 of the Pavia text, it shows some side reactions that i think that you will find helpful! Hope that this aids in your search! justin On Sun, 11 May 1997 archerka@plu.edu wrote: > > I'm having trouble with Question #1 on the Grignard Lab. How does benzene > form as a side product during the reaction using phenylmagnesium? > Thanks -Kristy > > From erickstd@plu.edu Mon May 12 15:48:56 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 PAA15215 for ; Mon, 12 May 1997 15:48:55 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IISCYD2XTS00H0VQ@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 12 May 1997 15:44:44 PDT Date: Mon, 12 May 1997 15:44:43 -0700 (PDT) From: THE PENGUIN Subject: Centrifuge To: O-Chem List Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII how long should the crystals be centriuged for??? the text never gives any set times. letting me know how long you centrifuged it would be a great help. thanks timmy XXXX X XXX/ XXXXXX\ XXXX XXXXX# X**XX### X***X##### X***X##### X**XX##### *XXXX### XXXXXX ^^^^^^^^^ Dooby Dooby Doo!! From maschhjt@plu.edu Mon May 12 17:24:33 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 RAA15872 for ; Mon, 12 May 1997 17:24:31 -0700 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IISGB5VYOG00GYVG@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 12 May 1997 17:20:32 PDT Date: Mon, 12 May 1997 17:20:31 -0700 (PDT) From: maschhjt@plu.edu Subject: Re: Centrifuge In-reply-to: To: organic1 , THE PENGUIN Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Timmy, Ileft mine in the centerfuge for quite some time. I wanted tomake sure that i got as much of the water out of the product as I could. I would suggest checking it peroidoicly to see how it looks, and then when you think you have gotten as much water out as you can, then let the crystals air dry! Justin On Mon, 12 May 1997, THE PENGUIN wrote: > how long should the crystals be centriuged for??? the text never gives > any set times. letting me know how long you centrifuged it would be a > great help. thanks > timmy > XXXX > X XXX/ > XXXXXX\ > XXXX > XXXXX# > X**XX### > X***X##### > X***X##### > X**XX##### > *XXXX### > XXXXXX > ^^^^^^^^^ > > Dooby Dooby Doo!! > >