From fryhle@u.washington.edu Thu Feb 20 14:20:15 1997 Received: from jason04.u.washington.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id OAA09292; Thu, 20 Feb 1997 14:20:13 -0800 Received: from homer07.u.washington.edu (homer07.u.washington.edu [140.142.77.11]) by jason04.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with ESMTP id OAA27420 for ; Thu, 20 Feb 1997 14:16:23 -0800 Received: from localhost (fryhle@localhost) by homer07.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with SMTP id OAA16484 for ; Thu, 20 Feb 1997 14:17:43 -0800 Date: Thu, 20 Feb 1997 14:17:43 -0800 (PST) From: Craig Fryhle Reply-To: Craig Fryhle To: Organic Chemistry I List Subject: Compliments! Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings, folks. I'm just writing to compliment all of you on the fact that there have been many helpful postings to this list from the class. You are helping to significantly stimulate the learning atmosphere of the class. Keep it up! I regret to say that the archive feature of the list has not been operating until today, however. From now on messages will be archived, and I will update the links in the course home page that lead to the archives about once a week. Have no fear, I do have record of how many postings each of you has made so far, however. Cheerio, 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 storeyad@plu.edu Thu Feb 20 15:16:18 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id PAA09565; Thu, 20 Feb 1997 15:16:17 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFN6A04UVA0043JW@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 20 Feb 1997 15:13:47 PST Date: Thu, 20 Feb 1997 15:13:44 -0800 (PST) From: storeyad@plu.edu Subject: Re: Chapter 2 prob 2.5e In-reply-to: To: super freak Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII HELP!!!! i got 2 different Rf values for my unknowns, and each of them correspond to a different analgesic Rf value. what should i do??? angela From lindebim@plu.edu Thu Feb 20 17:02:44 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id RAA10212; Thu, 20 Feb 1997 17:02:43 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFN9YZI36G005Q06@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 20 Feb 1997 17:00:10 PST Date: Thu, 20 Feb 1997 17:00:10 -0800 (PST) From: lindebim@plu.edu Subject: lab 4 To: Organic Chemlist Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Am I the only one whose ibuprofen did not show up on the TLC? Would it be beneficial to do the ibuprofen over again? Would I have to do it all over again, or just that one? Ingrid From joelm@plu.edu Thu Feb 20 17:20:50 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id RAA10336; Thu, 20 Feb 1997 17:20:49 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFNAMF2WEW005CXN@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 20 Feb 1997 17:18:17 PST Date: Thu, 20 Feb 1997 17:18:17 -0800 (PST) From: super freak Subject: lab similar rvalues To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII my ib and sal were about the same ht but were a mass diff color. were your unknown and two ref the same color as well as the same ht? ya might wanna check? hope it helps... lj ~~~~ joelm@plu.edu ~~~~ 'KISS ME BABY, I'M VACINATED!' --another crazy chic From storeyad@plu.edu Fri Feb 21 00:53:38 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id AAA14023; Fri, 21 Feb 1997 00:53:38 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFNQFSS04A005TZK@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 21 Feb 1997 00:51:05 PST Date: Fri, 21 Feb 1997 00:51:04 -0800 (PST) From: storeyad@plu.edu Subject: Re: lab 4 In-reply-to: To: lindebim@plu.edu Cc: Organic Chemlist Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII mine showed up, as did everyone elses that i have talked to. maybe it faded before you put it under the uv lamp, or maybe it blended with another analgesic, or something else random. i would suggest that you do that one again. sorry. angela On Thu, 20 Feb 1997 lindebim@plu.edu wrote: > Am I the only one whose ibuprofen did not show up on the TLC? Would it be > beneficial to do the ibuprofen over again? Would I have to do it all over > again, or just that one? Ingrid > > From youngcf@plu.edu Fri Feb 21 11:04:03 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id LAA17488; Fri, 21 Feb 1997 11:04:01 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFOBQHZD400020Q1@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 21 Feb 1997 11:01:26 PST Date: Fri, 21 Feb 1997 11:01:26 -0800 (PST) From: youngcf@plu.edu Subject: Student board meeting To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII 2/21/97: Today the student board gathered and discussed three main areas of concern. First, the role of the board is as follows, to express any questions and/or comments about class sessions, labs, and other information directly to Dr. Fryhle. This may be done by yourself of course, but if need be, the board will act as a conduit for any relevent questions and/or concerns. Secondly, the level of participation of individuals in learning groups must be equally distributed. Moreover, all individuals must comply with the distribution of tasks and work towards accomplishing the goal(s) at hand. Lastly, the student board will have an open study forum at least once a month for all to enjoy. This forum will be based on student/student question and answer periods and tutoring sessions. Times and place to be announced soon. Youngcf@plu.edu. From fickesje@plu.edu Fri Feb 21 14:04:06 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id OAA24539; Fri, 21 Feb 1997 14:04:05 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFOI1TKP0W00096N@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 21 Feb 1997 14:01:32 PST Date: Fri, 21 Feb 1997 14:01:32 -0800 (PST) From: fickesje@plu.edu To: Organic chem Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I need someone to explain van der waals forces to me. I know he went over it today in class but for some reason I am having a hard time understanding it. Thanks jen From vogega@plu.edu Fri Feb 21 15:09:20 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id PAA24909; Fri, 21 Feb 1997 15:09:19 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFOKBLUN800009HY@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 21 Feb 1997 15:06:43 PST Date: Fri, 21 Feb 1997 15:06:42 -0800 (PST) From: vogega@plu.edu Subject: Re: your mail In-reply-to: To: fickesje@plu.edu Cc: Organic chem Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII jen- van der waals forces occur because electrons are in motion. it is simply stating that at any given time, the electrons maybe more concentrated in one region of the electron cloud. This creates a temporary dipole (a slightly negative charge). When this molecule bumps into another molecule, the slight negative charge will be attracted to the slight positive charge. When the electrons are more concentrated in one particular area, it leaves another area partially positive. These two area (on different molecules) will be attracted to each other due to opposite attraction. This may not have helped you. It would be easier for me to draw you a picture. Imagine a metal circle with two beads(electrons) on it. The beats are moving around the circle (orbit). At some point in time, both beads may be right next to each other. This creates an unbalanced circle. If two unbalanced circles bumped into each other, they would try to counter balance each other. I hope this analogy helps. It may be a little confusing. Maybe someone else can explain it better. Gretchen Voge On Fri, 21 Feb 1997 fickesje@plu.edu wrote: > I need someone to explain van der waals forces to me. I know he > went over it today in class but for some reason I am having a hard time > understanding it. Thanks > jen > > From archerka@plu.edu Fri Feb 21 15:23:49 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id PAA25001; Fri, 21 Feb 1997 15:23:47 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFOKR7NK1C000BXY@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 21 Feb 1997 15:19:18 PST Date: Fri, 21 Feb 1997 15:19:17 -0800 (PST) From: archerka@plu.edu Subject: van der Waals forces To: organic chemistry list Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I'm going to try to explain van der Waals forces but if I'm wrong I would appreciate it if someone helped explain it to me. In a molecule the electrons are constantly moving around so sometimes one side of the molecule will have a little more of a negative charge or a positive charge than the other. Other molecules are drawn to these charged molecules so it creates a very weak bond. It's not a real bond that shares electrons, more like a hydrogen bond but weaker. I hope this is basically right or else I'll have to do a little more studing! K.Archer From frickeje@plu.edu Fri Feb 21 15:38:36 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id PAA25112; Fri, 21 Feb 1997 15:38:35 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFOLBWW6AA00083S@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 21 Feb 1997 15:36:00 PST Date: Fri, 21 Feb 1997 15:36:00 -0800 (PST) From: frickeje@plu.edu Subject: lab #4 To: Organic Chemistry List Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII When viewing the spots under UV light, did anyone else have one or two smaller fainter spots appear for; the unknown, reference, or ibuprofen? If so, what do they mean and do they affect the Rf values? Thanks freaks, John Fricke From mistkaam@plu.edu Fri Feb 21 15:45:27 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id PAA25184; Fri, 21 Feb 1997 15:45:27 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFOLKCJOLS000DJN@plu.edu> for organic1@rainier.chem.plu.edu; Fri, 21 Feb 1997 15:42:49 PST Date: Fri, 21 Feb 1997 15:42:46 -0800 (PST) From: mistkaam@plu.edu Subject: Re: lab #4 In-reply-to: To: frickeje@plu.edu Cc: Organic Chemistry List Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Jen, for the referece spot, there should be a couple of spots. The reference has a little bit of all of the drugs, so there should be more than one spot. On the ibuprofen, I had a big blob and for my unknown, there was just one spot. On Fri, 21 Feb 1997 frickeje@plu.edu wrote: > When viewing the spots under UV light, did anyone else have one or two > smaller fainter spots appear for; the unknown, reference, or ibuprofen? > If so, what do they mean and do they affect the Rf values? > > Thanks freaks, > > John Fricke > > > From LStandifer@msn.com Fri Feb 21 23:59:01 1997 Received: from upsmot03.msn.com by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id XAA27837; Fri, 21 Feb 1997 23:59:00 -0800 Received: from upmajb04.msn.com ([204.95.110.81]) by upsmot03.msn.com (8.6.8.1/Configuration 4) with SMTP id XAA18571 for ; Fri, 21 Feb 1997 23:50:53 -0800 Date: Sat, 22 Feb 97 07:59:30 UT From: "LeRoy Standifer" Message-Id: To: organic1 Subject: TOJC Identity Crisis Dr. Fryhle and Group 7 members: Please note: my name and the name on my e-mail account do not match. Any messages you receive from L. Standifer are actually from me, Carol Krancich (his better half). Sorry if this causes any confusion. Dr. Fryhle, please don't give him credit for my TOJC postings. You may, however, blame him for any bungled labs or tests! Signed, Lost in Space From storeyad@plu.edu Sat Feb 22 01:08:01 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id BAA28522; Sat, 22 Feb 1997 01:08:00 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFP57WJ1KS000NV5@plu.edu> for organic1@rainier.chem.plu.edu; Sat, 22 Feb 1997 01:05:24 PST Date: Sat, 22 Feb 1997 01:05:23 -0800 (PST) From: storeyad@plu.edu Subject: Re: lab #4 In-reply-to: To: frickeje@plu.edu Cc: Organic Chemistry List Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII i know that someone else has already answered this one- but i think that they missed one part. you should take the Rf values for ALL of the spots, even if you get multiple ones for a single drug, because that just means there were more than one of the compounds in the drug. angela ps- did anyone else that tested unknown A get one of the spots to be really close to 2 different analgesics??? confusion.. On Fri, 21 Feb 1997 frickeje@plu.edu wrote: > When viewing the spots under UV light, did anyone else have one or two > smaller fainter spots appear for; the unknown, reference, or ibuprofen? > If so, what do they mean and do they affect the Rf values? > > Thanks freaks, > > John Fricke > > > From smithtw@plu.edu Sun Feb 23 13:14:45 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id NAA09749; Sun, 23 Feb 1997 13:14:44 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFR8W9L868001735@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 23 Feb 1997 13:12:07 PST Date: Sun, 23 Feb 1997 13:12:07 -0800 (PST) From: smithtw@plu.edu Subject: question... To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII In the chapter 3 reading, where does the number (55.5M) for the concentration of water come from? Did I miss it somewhere in the reading or do I just not remember it or what? Tobin From schelvac@plu.edu Sun Feb 23 18:35:41 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id SAA11455; Sun, 23 Feb 1997 18:35:40 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFRK46KAKK001QGB@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 23 Feb 1997 18:33:05 PST Date: Sun, 23 Feb 1997 18:33:05 -0800 (PST) From: schelvac@plu.edu Subject: chapter 3 concepts To: organic1 Reply-to: schelvac@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I am having trouble understanding the inductive and resonance effects that are described in sections 3.7B, 3.9A, 3.9B, and 3.9C. Could somebody please explain these concepts to me? Possibly in relation to problem #3.10. Thanks, Alethea From bekemj@plu.edu Sun Feb 23 19:36:46 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id TAA11794; Sun, 23 Feb 1997 19:36:45 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFRM8W9KWW001LSI@plu.edu> for Organic1@rainier.chem.plu.edu; Sun, 23 Feb 1997 19:34:09 PST Date: Sun, 23 Feb 1997 19:34:09 -0800 (PST) From: bekemj@plu.edu Subject: lab To: Organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII When determining Rf values in the recent lab, I found three main "levels" where the dots appeared to correspond to other dots. Therefore, I found the Rf value for each of the three levels and applied that Rf value to any "drug column" that had a spot on that level. Is this too general? Should I measure each dot individually? I am assuming that the Rf values will differ so remotly that they will be lost in significant figures. Do your results correspond with this assumption? Mike B. From taylormr@plu.edu Sun Feb 23 21:08:58 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id VAA12317; Sun, 23 Feb 1997 21:08:57 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFRPG7ARXC001U3X@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 23 Feb 1997 21:06:21 PST Date: Sun, 23 Feb 1997 21:06:20 -0800 (PST) From: MICHELE Subject: Re: question... In-reply-to: To: smithtw@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Tobin, On page 96 of Chapter three, it explains that the concentration of water is essentially constant (55.5M). Because of this, we can rewrite the expression for the constant as Ka. Also, when doing problems that involve constants, the information needed is usually given. As in the case of the concentration for water. Hope this helps. Michele On Sun, 23 Feb 1997 smithtw@plu.edu wrote: > In the chapter 3 reading, where does the number (55.5M) for the > concentration of water come from? Did I miss it somewhere in the reading > or do I just not remember it or what? > Tobin > > From hendrycl@plu.edu Sun Feb 23 23:02:59 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id XAA12931; Sun, 23 Feb 1997 23:02:59 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFRTFGVW5S001WGF@plu.edu> for organic1@rainier.chem.plu.edu; Sun, 23 Feb 1997 23:00:17 PST Date: Sun, 23 Feb 1997 23:00:17 -0800 (PST) From: hendrycl@plu.edu Subject: 3.4, KA calculation To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Problem 3.4 tells us that we begin with a .1M aqueous solution of formic acid. The solution manual states " 1.0 - x = [HCO2H] at equilibrium ". Shouldn't it be .1 - x = [HCO2H] at equilibrium? A typo? If not I'd appreciate someone describing to me how to complete the problem. chase From harriscr@plu.edu Mon Feb 24 00:43:52 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id AAA13789; Mon, 24 Feb 1997 00:43:52 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFRWYP1TEA0022SI@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 24 Feb 1997 00:41:17 PST Date: Mon, 24 Feb 1997 00:41:16 -0800 (PST) From: harriscr@plu.edu Subject: pKa's To: Organic chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Hey guys: I'm having trouble understanding what pKa's actually are. Could someone please help me out here. Is there any way to convert PKa's into pH values or that a completly different thing? Thanks, Clayton From fryhle@u.washington.edu Mon Feb 24 09:35:26 1997 Received: from jason01.u.washington.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id JAA16788; Mon, 24 Feb 1997 09:35:25 -0800 Received: from homer23.u.washington.edu (homer23.u.washington.edu [140.142.77.3]) by jason01.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with ESMTP id JAA20188 for ; Mon, 24 Feb 1997 09:27:33 -0800 Received: from localhost (fryhle@localhost) by homer23.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with SMTP id JAA135168 for ; Mon, 24 Feb 1997 09:32:51 -0800 Date: Mon, 24 Feb 1997 09:32:51 -0800 (PST) From: Craig Fryhle To: Organic Chemistry I List Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII help organic1 subscribers ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From charbogd@plu.edu Mon Feb 24 11:26:52 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id LAA17511; Mon, 24 Feb 1997 11:26:51 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFSJEMO0Z8002ELB@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 24 Feb 1997 11:24:05 PST Date: Mon, 24 Feb 1997 11:24:03 -0800 (PST) From: Dane Subject: Re: 3.4, KA calculation In-reply-to: To: hendrycl@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII chase Your solution manual is unique, 1.0 is definitely a typo! The value is 0.1 in the correct manual. gabe On Sun, 23 Feb 1997 hendrycl@plu.edu wrote: > > Problem 3.4 tells us that we begin with a .1M aqueous solution of formic > acid. The solution manual states " 1.0 - x = [HCO2H] at equilibrium ". > Shouldn't it be .1 - x = [HCO2H] at equilibrium? A typo? If not I'd > appreciate someone describing to me how to complete the problem. > > chase > > From charbogd@plu.edu Mon Feb 24 11:30:05 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id LAA17548; Mon, 24 Feb 1997 11:30:04 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFSJIS9VNG002ELB@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 24 Feb 1997 11:27:24 PST Date: Mon, 24 Feb 1997 11:27:24 -0800 (PST) From: Dane Subject: Re: pKa's In-reply-to: To: harriscr@plu.edu Cc: Organic chemistry Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Clayton, Do you understand what Ka's are? Because if you do, pKa's are easy, just take the -log of a Ka value and you have the pKa. This is just a way to make it so that we don't have to write/say huge numbers or miniscule numbers when describing the acidity constant. gabe On Mon, 24 Feb 1997 harriscr@plu.edu wrote: > > Hey guys: > > I'm having trouble understanding what pKa's actually are. Could someone > please help me out here. Is there any way to convert PKa's into pH values > or that a completly different thing? > > Thanks, > Clayton > > > From youngcf@plu.edu Mon Feb 24 13:31:29 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id NAA18258; Mon, 24 Feb 1997 13:31:28 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFSNQQK4I8002ALD@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 24 Feb 1997 13:28:25 PST Date: Mon, 24 Feb 1997 13:28:24 -0800 (PST) From: youngcf@plu.edu Subject: bond strength To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII HELP: In any carbon based compound, does the double bond in a carbon-carbon bond require more energy to break and to stay a double bond? Likewise for a triple bond? Youngcf@plu.edu. From steelecl@plu.edu Mon Feb 24 18:28:34 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id SAA20112; Mon, 24 Feb 1997 18:28:33 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFSY5O5IAO002HGG@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 24 Feb 1997 18:25:57 PST Date: Mon, 24 Feb 1997 18:25:57 -0800 (PST) From: steelecl@plu.edu To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII In class today we discussed that whether the reaction will occur (or in which direction it will occur) depends on electronegativity and resonance. I understood the electronegativity, but I do not see how the arrangement of atoms will change the acidity. Can someone please explain this more clearly? Caroline From 107744.2473@compuserve.com Mon Feb 24 20:29:44 1997 Received: from arl-img-5.compuserve.com by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id UAA20768; Mon, 24 Feb 1997 20:29:43 -0800 Received: by arl-img-5.compuserve.com (8.6.10/5.950515) id XAA04501; Mon, 24 Feb 1997 23:27:08 -0500 Date: Mon, 24 Feb 1997 23:26:45 -0500 From: "howard r. kletke" <107744.2473@compuserve.com> Subject: Relative strengths of conjugate bases To: unknown Message-ID: <199702242326_MC2-11AA-2ED2@compuserve.com> Question: In today's lecture we talked about the relative strengths of conjugate bases. In the example, that compared sulfuric acid's conjugate base to water's conjugate base, which was the stronger base? From what I understood "the less happy the negative charge, the stronger the base." Would this mean that water's conjugate base is stronger? Thankyou, Monica From williasl@plu.edu Mon Feb 24 20:46:40 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id UAA20895; Mon, 24 Feb 1997 20:46:39 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFT2YTA1CW002ZN4@plu.edu> for Organic1@rainier.chem.plu.edu; Mon, 24 Feb 1997 20:43:59 PST Date: Mon, 24 Feb 1997 20:43:58 -0800 (PST) From: williasl@plu.edu Subject: Re: Relative strengths of conjugate bases In-reply-to: <199702242326_MC2-11AA-2ED2@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 Yes, it would mean that water's conjugate base is stronger. Another way to think of it is that the weaker the acid, the stronger the conjugate base, and since water is a weaker acid than sulfuric acid, it's base would be stronger than the base of sulfuric acid. Does that help? Sarah On Mon, 24 Feb 1997, howard r. kletke wrote: > Question: > In today's lecture we talked about the relative strengths of > conjugate bases. In the example, that compared sulfuric acid's conjugate > base to water's conjugate base, which was the stronger base? From what I > understood "the less happy the negative charge, the stronger the base." > Would this mean that water's conjugate base is stronger? > > Thankyou, > Monica > From larsenak@plu.edu Mon Feb 24 20:49:38 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id UAA20934; Mon, 24 Feb 1997 20:49:37 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFT32BNWO00031JN@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 24 Feb 1997 20:46:49 PST Date: Mon, 24 Feb 1997 20:46:48 -0800 (PST) From: larsenak@plu.edu Subject: pH and pKa To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII What is the difference between pH and pKa? Andy From bowersmy@plu.edu Mon Feb 24 21:38:15 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id VAA21174; Mon, 24 Feb 1997 21:38:14 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFT4RO368W0031I9@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 24 Feb 1997 21:35:30 PST Date: Mon, 24 Feb 1997 21:35:29 -0800 (PST) From: bowersmy@plu.edu Subject: learning group #3 To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I looked all over, and can't find the pKa for the conjugate acid of NaHCO3. Can anyone give me a hint on where to find it, or at least on how to estimate it? From williasl@plu.edu Mon Feb 24 21:49:42 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id VAA21265; Mon, 24 Feb 1997 21:49:41 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFT55SEYOW0031GV@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 24 Feb 1997 21:46:57 PST Date: Mon, 24 Feb 1997 21:46:52 -0800 (PST) From: williasl@plu.edu Subject: Re: pH and pKa In-reply-to: To: larsenak@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII pH is the negative log of the Hydronium ion concentration, and pKa is the negative log of the acidity constant of a compound. Does that help? Sarah On Mon, 24 Feb 1997 larsenak@plu.edu wrote: > What is the difference between pH and pKa? > > Andy > > From fryhle@u.washington.edu Mon Feb 24 21:53:51 1997 Received: from jason05.u.washington.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id VAA21299; Mon, 24 Feb 1997 21:53:51 -0800 Received: from homer21.u.washington.edu (homer21.u.washington.edu [140.142.77.1]) by jason05.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with ESMTP id VAA07246 for ; Mon, 24 Feb 1997 21:48:14 -0800 Received: from localhost (fryhle@localhost) by homer21.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with SMTP id VAA39756 for ; Mon, 24 Feb 1997 21:51:16 -0800 Date: Mon, 24 Feb 1997 21:51:16 -0800 (PST) From: Craig Fryhle To: Organic Chemistry I List Subject: Chapter 3 Quiz, etc. Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings, Organikers. I forgot to give you the Chapter 3 quiz today! In order to keep the ball moving we will beginn the day on Wednesday will the Ch 3 quiz, then move on to the beginning of material from Ch 4. Here's the schedule: Wednesday 2/24 Ch 3 Quiz, Begin material in Ch 4 Friday 2/26 Ch 3 Learning Group Presentations Monday 3/3 Chapter 4 Quiz Wednesday 3/5 Ch 4 Learning Group Presentations Friday 3/7 First Exam I hope that clears things up. Shortly I will send a message with some info relevant to the isoamyl acetate lab. Before that, however, I hope you will excuse my postings of some things that aren't relevant to you anymore, but that I want to get posted so that they can be in the web-accessible archive for the email list. Just hit delete for them. CBF ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From fryhle@u.washington.edu Mon Feb 24 21:57:49 1997 Received: from jason03.u.washington.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id VAA21328; Mon, 24 Feb 1997 21:57:47 -0800 Received: from homer21.u.washington.edu (homer21.u.washington.edu [140.142.77.1]) by jason03.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with ESMTP id VAA13802 for ; Mon, 24 Feb 1997 21:52:11 -0800 Received: from localhost (fryhle@localhost) by homer21.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with SMTP id VAA26992 for ; Mon, 24 Feb 1997 21:55:13 -0800 Date: Mon, 24 Feb 1997 21:55:12 -0800 (PST) From: Craig Fryhle To: Organic Chemistry I List Subject: Learning Group Problem, Ch 1 Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Organic Chemistry I: Chemistry 232 Learning Group Problem - Chapter 1 All groups should work on this problem. We will discuss it and finish work on it in class on Wednesday February 12. This problem will not be graded, but your group might be chosen at random to present your work on February 12. Consider the compound with the following condensed molecular formula. CH3CHOHCH=CH2 1. Write a full dash structural formula for this compound. 2. Show all nonbonding electron pairs on your dash structural formula. 3. Indicate any formal charges that may be present in the molecule. 4. Label the hybridization state at every carbon atom and the oxygen. 5. Draw a three-dimensional perspective representation for this compound showing approximate bond angles as clearly as possible. Use ordinary lines to indicate bonds in the plane of the paper, bold wedges for bonds in front of the paper, and dashed wedges for bonds behind the pr. 6. Label all the bond angles in your three-dimensional structure. 7. Indicate the polarity of any bonds that would be expected to be significantly polar. Use bond moment arrows, as employed on page 40 of the text. 8. Draw a bond-line formula for this compound. ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From fryhle@u.washington.edu Mon Feb 24 21:59:26 1997 Received: from jason05.u.washington.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id VAA21359; Mon, 24 Feb 1997 21:59:26 -0800 Received: from homer21.u.washington.edu (homer21.u.washington.edu [140.142.77.1]) by jason05.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with ESMTP id VAA25214 for ; Mon, 24 Feb 1997 21:53:50 -0800 Received: from localhost (fryhle@localhost) by homer21.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with SMTP id VAA82564 for ; Mon, 24 Feb 1997 21:56:51 -0800 Date: Mon, 24 Feb 1997 21:56:51 -0800 (PST) From: Craig Fryhle To: Organic Chemistry I List Subject: Learning Group Problem, Ch 2 Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Chemistry 232: Organic Chemistry I Chapter 2 Learning Group Problem Consider the molecular formula C4H8O2. a) Write structures for at least 15 different compounds that all have the molecular formula C4H8O2. b) Provide at least one example each of a structure written using the dash format, the condensed format, the bond-line format, and full three-dimensional format. Use your choice of format for the remaining structures. c) Identify four different functional groups from among your structures. Circle and name them on representative structures. d) If any compounds have atoms where the formal charge is other than zero, indicate the formal charge on the appropriate atom(s) and the overall charge for the molecule. e) Identify which types of intermolecular forces would be possible in pure samples of each of these compounds. f) Pick five structures you have drawn and predict their order with respect to trend in increasing boiling point. g) Explain the order of boiling points on the basis of intermolecular forces and polarity. ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From fryhle@u.washington.edu Mon Feb 24 22:01:27 1997 Received: from jason03.u.washington.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id WAA21416; Mon, 24 Feb 1997 22:01:27 -0800 Received: from homer21.u.washington.edu (homer21.u.washington.edu [140.142.77.1]) by jason03.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with ESMTP id VAA13758 for ; Mon, 24 Feb 1997 21:55:51 -0800 Received: from localhost (fryhle@localhost) by homer21.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with SMTP id VAA15526 for ; Mon, 24 Feb 1997 21:58:52 -0800 Date: Mon, 24 Feb 1997 21:58:52 -0800 (PST) From: Craig Fryhle To: Organic Chemistry I List Subject: Learning Group Problem, Ch 3 Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Organic Chemistry I: Chemistry 232 Learning Group Problem - Chapter Three Suppose that you carried out the following synthesis of 3-methylbutyl ethanoate (isoamyl acetate): trace H2SO4 acetic acid (excess) + 3-methyl-1-butanol ----------------> 3-methylbutyl ethanoate + H2O As evident from the chemical equation, the reaction was conducted by mixing 3-methyl-1-butanol (also called isoamyl alchohol or isopentyl alcohol), an excess of acetic acid (ethanoic acid by its IUPAC name), and a trace of sulfuric acid (which serves as a catalyst). This reaction is an equilibrium reaction, so it is expected that not all of the starting materials will be consumed. The equilibrium should lie quite far to the right due to the excess of acetic acid used, but not completely. After the reaction had proceeded for the desired length of time, isolation of the desired product from the reaction mixture was begun by adding a volume of aqueous sodium bicarbonate (5% NaHCO3, a basic solution) roughly equal to the volume of the reaction mixture. At this point bubbling occurred, and the result was a mixture consisting of two layers - a basic aqueous layer and an organic layer. The layers were separated and the aqueous layer was removed. The process of adding aqueous sodium bicarbonate to the layer of organic materials and separating the layers was repeated twice again. The predominantly aqueous layers removed each time were combined together after each separation. The organic layer that remained after the three bicarbonate extractions was subjected to distillation in order to obtain a pure sample of 3-methylbutyl ethanoate (isoamyl acetate). 1) List all the chemical species likely to be present at the end of the reaction but before adding aqueous NaHCO3. Note that the H2SO4 was not consumed (since it is a catalyst), and is thus still available to donate a proton to atoms that can be protonated. 2) Use a table of pKa values, such as the one in Chapter 3 of the textbook, to estimate pKa values for any potentially acidic hydrogens in each of these species (or for the conjugate acid). The pKa for H2CO3 is 3.7 and the pKa for HCO3- is 10.2. 3) Write out chemical equations for all the acid-base reactions that you would predict to occur (based on the pKa values you assumed) when the species you listed above encounter the aqueous sodium bicarbonate solution. (Hint: consider whether or not each species might be an acid that could react with NaHCO3.) 4) a) Explain on the basis of polarities and solubility why separate layers formed when aqueous sodium bicarbonate was added to the reaction mixture. (Hint: most organic compounds that are ions(of reasonable size) are soluble in water, as are neutral organic compounds of four carbons or less.) b) List the chemical species likely to be present in i) the the organic layer, and ii) the aqueous layer, after the reaction with NaHCO3. c) Why was the aqueous sodium bicarbonate extraction step repeated three times? lgp3-97.doc ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From taylormr@plu.edu Mon Feb 24 22:17:42 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id WAA21538; Mon, 24 Feb 1997 22:17:41 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFT659OW4W002WGO@plu.edu> for organic1@rainier.chem.plu.edu; Mon, 24 Feb 1997 22:14:46 PST Date: Mon, 24 Feb 1997 22:14:41 -0800 (PST) From: MICHELE Subject: Re: bond strength In-reply-to: To: youngcf@plu.edu Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII In all carbon based compounds, the bond strength strengthens with the number of bonds present (ex. triple bonds are stronger than double bonds and double bonds are stronger than single bonds), because of this, the carbon-carbon double bonds require more energy to stay and break a double bond. The same goes for a triple bond. Michele Taylor On Mon, 24 Feb 1997 youngcf@plu.edu wrote: > > HELP: > > In any carbon based compound, does the double bond in a carbon-carbon > bond require more energy to break and to stay a double bond? Likewise for > a triple bond? > > Youngcf@plu.edu. > > From fryhle@u.washington.edu Mon Feb 24 22:20:49 1997 Received: from jason04.u.washington.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id WAA21571; Mon, 24 Feb 1997 22:20:49 -0800 Received: from homer21.u.washington.edu (homer21.u.washington.edu [140.142.77.1]) by jason04.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with ESMTP id WAA24338 for ; Mon, 24 Feb 1997 22:16:51 -0800 Received: from localhost (fryhle@localhost) by homer21.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with SMTP id WAA39810 for ; Mon, 24 Feb 1997 22:18:14 -0800 Date: Mon, 24 Feb 1997 22:18:14 -0800 (PST) From: Craig Fryhle Reply-To: Craig Fryhle To: Organic Chemistry I List Subject: Isoamyl Acetate (Banana Oil) Lab Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Organic Chemistry Lab I: Chemistry 234 Supplemental Instructions for Experiment 6, Synthesis of Isopentyl Acetate In addition to the comments below, read all Technique sections cited in the lab procedure. If your basket of equipment does not contain a magnetic spin vane or there are no stirrer- hot plates available, use a couple of boiling stones to prevent bumping of the mixture during reflux and distillation. Heat your reaction by clamping the reaction set-up in an aluminum block on a stirrer-hot plate, instead of a sand bath. Use a thermometer in the block to monitor temperature. Be careful of the thermometers, as they are easily broken when used in this capacity. No one enjoys a mercury spill! Note the proper direction and rate (slow!) of water flow through the condensor during the reflux. If time is short for you, there are two possible points within the experiment where you may halt the experiment and continue at a later time. In each case, transfer the reaction mixture to an ordinary vial that is properly labeled, and ask for it to be placed on the alphabetical strorage shelves for later use. We do not have enough of the conical reaction vials to have them tied up in storage. You can transfer your material back into a reaction vial if necessary when you continue the experiement. Here are the two stopping points: 1) You can take a break immediately after the initial reflux step. The reaction mixture can be transferred to an ordinary vial and stored at this time, before proceeding to do the sodium bicarbonate extractions. 2) The organic layer can be stored after the sodium bicarbonate extractions and drying with anhydrous sodium sulfate (that is, before the distillation step). Again, use an ordinary vial for storage, properly labeled of course. The crude ester can be stored over anhydrous sodium sulfate in a tightly sealed storage vial. As to determination of the boiling point, do this *during the first distillation*. Simply omit the Ca Cl2 drying tube from the distillation apparatus shown in Figure 8-7A so that you can suspend a thermometer inside the neck of the setup. Arrange it so that the thermometer bulb is well-surrounded by the vapors of the boiling liquid as the vapors travel up to the well in the Hickman still head. Then, essentially the highest temperature (range) you record during the distillation serves as your boiling point. At the completion of the distillation, transfer your sample to a plain sample vial for grading. *Omit* the microscale boiling point determination called for at the end of the experiment. ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 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 malonekn@plu.edu Tue Feb 25 10:54:40 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id KAA25688; Tue, 25 Feb 1997 10:54:39 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFTWL766LC003KKB@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 25 Feb 1997 10:52:00 PST Date: Tue, 25 Feb 1997 10:51:59 -0800 (PST) From: malonekn@plu.edu Subject: Re: your mail In-reply-to: To: vogega@plu.edu Cc: fickesje@plu.edu, Organic chem Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII hey there. I just had a minor addition to make to the definition below and that is that the formation of a temporary dipole associated with van der waals forces is not entirely random, but that as one slightly positive end of a molecule bumps into another molecule, it CAUSES the electrons in that molecule to move closer to that end, so that the molecules are momentarily attracted to one another. The difference between this explanation and the one below is subtle, but I think it's still important. --kath On Fri, 21 Feb 1997 vogega@plu.edu wrote: > jen- > van der waals forces occur because electrons are in motion. it is > simply stating that at any given time, the electrons maybe more > concentrated in one region of the electron cloud. This creates a > temporary dipole (a slightly negative charge). When this molecule bumps > into another molecule, the slight negative charge will be attracted to the > slight positive charge. When the electrons are more concentrated in one > particular area, it leaves another area partially positive. These two > area (on different molecules) will be attracted to each other due to > opposite attraction. This may not have helped you. It would be easier > for me to draw you a picture. Imagine a metal circle with two > beads(electrons) on it. The beats are moving around the circle (orbit). > At some point in time, both beads may be right next to each other. This > creates an unbalanced circle. If two unbalanced circles bumped into each > other, they would try to counter balance each other. I hope this analogy > helps. It may be a little confusing. Maybe someone else can explain it > better. > Gretchen Voge > > On Fri, 21 Feb 1997 fickesje@plu.edu wrote: > > > I need someone to explain van der waals forces to me. I know he > > went over it today in class but for some reason I am having a hard time > > understanding it. Thanks > > jen > > > > > > From raquetce@plu.edu Tue Feb 25 14:58:33 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id OAA27598; Tue, 25 Feb 1997 14:58:32 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFU53EVIR4003OFT@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 25 Feb 1997 14:55:45 PST Date: Tue, 25 Feb 1997 14:55:44 -0800 (PST) From: raquetce@plu.edu Subject: lab To: org chem list Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Curious: In this week's lab we use a spin vane to stir our solution. I was told that if the spin vane did not work then to just let it boil without it. I am just curious if it would make a difference in the result of the lab without the spin vane. Also, if it is affected, what is the result? -CR From fryhle@u.washington.edu Tue Feb 25 16:08:24 1997 Received: from jason02.u.washington.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id QAA28164; Tue, 25 Feb 1997 16:08:23 -0800 Received: from homer22.u.washington.edu (homer22.u.washington.edu [140.142.77.2]) by jason02.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with ESMTP id QAA13646 for ; Tue, 25 Feb 1997 16:03:46 -0800 Received: from localhost (fryhle@localhost) by homer22.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with SMTP id QAA125550 for ; Tue, 25 Feb 1997 16:05:47 -0800 Date: Tue, 25 Feb 1997 16:05:47 -0800 (PST) From: Craig Fryhle To: Organic Chemistry I List Subject: Spin Vanes in Rxn Vials Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings, lab students. Whenever a solution is boiling/will boil, it is necessary to do something to keep it from bumping (vaporizing in large bubbles that may splash the reaction unnecesarily). Agitation by a spin vane will do this. Even if the spin vane is not spinning but is simply oscillating the reaction will get sufficient agitation. Another alternative is to use a couple of boiling stones (available at the stockroom window). Yet a final option is to manually shake/rock the reaction mixture from time to time (although this may not be frequent enough to prevent bumping). Reactions must also be mixed in order to insure that all reagents have equal opportunity to react with each other. Thermal currents can do this in a mixture below the bp, but stirring is the most effective way and also guards against bumping if/when the mixture boils. Again, hand agitation every so often can accomplish mixing for this purpose. CBF On Tue, 25 Feb 1997 raquetce@plu.edu wrote: > > Curious: > > In this week's lab we use a spin vane to stir our solution. I was > told that if the spin vane did not work then to just let it boil without > it. I am just curious if it would make a difference in the result of the > lab without the spin vane. Also, if it is affected, what is the result? > > -CR > > ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ 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 HARSTALJ@plu.edu Tue Feb 25 16:19:29 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id QAA28223; Tue, 25 Feb 1997 16:19:28 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFU7URY10W0040CT@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 25 Feb 1997 16:16:42 PST Date: Tue, 25 Feb 1997 16:16:41 -0800 (PST) From: FAT-N-SASSY Subject: the first lab report... To: organic1 Message-id: <01IFU7URYMOY0040CT@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 Does anyone remember when we were supposed to get those back? For some reason I thought this afternoon, but I didn't see any labs outside Dr. Fryhle's door when I checked. Also, when are our second lab reports due? Tonight or tomorrow night? Leslie From harstalj@plu.edu Tue Feb 25 16:22:43 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id QAA28261; Tue, 25 Feb 1997 16:22:42 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFU81YLPIA0040CT@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 25 Feb 1997 16:20:04 PST Date: Tue, 25 Feb 1997 16:20:04 -0800 (PST) From: FAT-N-SASSY Subject: RE: chapter 3 concepts To: organic1 Cc: HARSTALJ@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII OOPS. I THINK THE FIRST TIME I TRIED TO SEND THIS I SENT ONE JUST TO ALTHEA... NOT THE WHOLE LIST SERVE. IF I'M WRONG AND YOU ALL ALREADY HAVE A COPY OF THIS JUST DELETE IT. OTHERWISE, HERE IS SOMETHING I WROTE YESTERDAY AND TRIED TO SEND. Althea Resonance effects and inductive effects are two different ways of explaining why a carboxylic acid would have a greater tend to dissociate in an acid-base reaction than a corresponding alcohol. The most important thing to undersand about inductive effects is that the carbonyl group attracts the electrons powerfully away from the carbon, creating a highly polar molecule. The carbonyl group is extremely negative because of the electrons it attracts with its large electronegativity, and the carbon is very positive, having had a large degree of it's negative charge drawn away from it. The two polar ends of the molecule separate much more easily then, than they do in an alcohol, where no highly electronegative carbonyl group is tugging all the electrons away from the rest of the molecule. (There is an explanation of how electronegativity affects the strength of an acid or a base on pages 102 and 103 in the book...) The resonance explanation confuses me too, though, so I don't think I should try to explain it myself. What I want to know about resonance effects is this: if the resonance structure makes the carboxylic acid more stable, how can its strength as an acid increase? I thought that more stable ions and anions were less likely to react... I know this has to do with free energy which we haven't discussed in class yet, but if anyone thinks they understand this now, I would sure appreciate them trying to explain it to me! Thanks y'all, and Althea, I hope the part about inductive effects was helpful at least. Leslie From harstalj@plu.edu Tue Feb 25 16:24:13 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id QAA28296; Tue, 25 Feb 1997 16:24:12 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFU83TE8XO0040CT@plu.edu> for ORGANIC1@RAINIER.CHEM.PLU.EDU; Tue, 25 Feb 1997 16:21:35 PST Date: Tue, 25 Feb 1997 16:21:33 -0800 (PST) From: FAT-N-SASSY Subject: RE: pKa's To: ORGANIC1 Cc: HARSTALJ@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII SORRY GUYS. I THINK I MESSED UP WITH THIS ONE TOO. IF I'M WRONG AND YOU ALREADY HAVE IT, LIKE I SAID, IGNORE IT. OTHERWISE, HERE IS _ANOTHER_ SOMETHING I TRIED TO POST YESTERDAY... Clayton, That's a good question! I'm not sure how you would go about converting a pKa value to a pH value, but I assume that you can since pKa is said to be "analogous to" pH. So, no, they are not completely unrelated. Both are measurements of acidity and both are the negative log of the concentration of ions. I think that pH is the negative log of the concentration of the hydronium ion (in molarity units???), so it would be different from pKa in that it measures the molarity of one ion instead of of several ions and molecules in a reaction. Does anyone else know anything about this to help us out? Leslie From raquetce@plu.edu Tue Feb 25 16:49:20 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id QAA28433; Tue, 25 Feb 1997 16:49:19 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFU8YVXMJK003YCH@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 25 Feb 1997 16:46:38 PST Date: Tue, 25 Feb 1997 16:46:37 -0800 (PST) From: raquetce@plu.edu Subject: Re: the first lab report... In-reply-to: <01IFU7URYMOY0040CT@plu.edu> To: FAT-N-SASSY Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII We are supposed to get the lab reports back today. There is a white envelope outside of his door labeled chem 232. The second lab is due tomorrow by 6:00pm. I hope this helps. -CR On Tue, 25 Feb 1997, FAT-N-SASSY wrote: > Does anyone remember when we were supposed to get those back? For some reason I > thought this afternoon, but I didn't see any labs outside Dr. Fryhle's door > when I checked. Also, when are our second lab reports due? Tonight or tomorrow > night? > > Leslie > From carlisel@plu.edu Tue Feb 25 22:04:11 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id WAA01009; Tue, 25 Feb 1997 22:04:08 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFUJX94F3K0005KC@plu.edu> for organic1@rainier.chem.plu.edu; Tue, 25 Feb 1997 22:00:51 PST Date: Tue, 25 Feb 1997 22:00:42 -0800 (PST) From: carlisel@plu.edu Subject: Re: the first lab report... In-reply-to: <01IFU7URYMOY0040CT@plu.edu> To: FAT-N-SASSY Cc: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII I know this question has already been answered, but I remember him saying that the lab reports were due tomorrow by class time and not tomorrow night. I just wanted to clear up any confusion and to ensure everyone gets them in on time. From fryhle@u.washington.edu Tue Feb 25 22:27:49 1997 Received: from jason03.u.washington.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id WAA01166; Tue, 25 Feb 1997 22:27:49 -0800 Received: from homer25.u.washington.edu (homer25.u.washington.edu [140.142.78.15]) by jason03.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with ESMTP id WAA18346; Tue, 25 Feb 1997 22:22:10 -0800 Received: from localhost (fryhle@localhost) by homer25.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with SMTP id WAA79354; Tue, 25 Feb 1997 22:25:13 -0800 Date: Tue, 25 Feb 1997 22:25:13 -0800 (PST) From: Craig Fryhle Reply-To: Craig Fryhle To: FAT-N-SASSY cc: organic1 Subject: Re: the first lab report... In-Reply-To: <01IFU7URYMOY0040CT@plu.edu> Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Leslie, et al, I placed the first set of graded lab reports outside my door Monday afternoon at 3:30. The second lab report is due Wednesday morning before class. CBF On Tue, 25 Feb 1997, FAT-N-SASSY wrote: > Does anyone remember when we were supposed to get those back? For some reason I > thought this afternoon, but I didn't see any labs outside Dr. Fryhle's door > when I checked. Also, when are our second lab reports due? Tonight or tomorrow > night? > > 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 fryhle@u.washington.edu Tue Feb 25 22:34:10 1997 Received: from jason03.u.washington.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id WAA01236; Tue, 25 Feb 1997 22:34:09 -0800 Received: from homer25.u.washington.edu (homer25.u.washington.edu [140.142.78.15]) by jason03.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with ESMTP id WAA16456; Tue, 25 Feb 1997 22:28:31 -0800 Received: from localhost (fryhle@localhost) by homer25.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with SMTP id WAA33050; Tue, 25 Feb 1997 22:31:33 -0800 Date: Tue, 25 Feb 1997 22:31:33 -0800 (PST) From: Craig Fryhle To: FAT-N-SASSY cc: organic1 Subject: RE: chapter 3 concepts In-Reply-To: Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII On Tue, 25 Feb 1997, FAT-N-SASSY wrote: >...... > The resonance explanation confuses me too, though, so I don't think I > should try to explain it myself. What I want to know about resonance effects is > this: if the resonance structure makes the carboxylic acid more stable, how can > its strength as an acid increase? I thought that more stable ions and anions > were less likely to react... I know this has to do with free energy which we > haven't discussed in class yet, but if anyone thinks they understand this now, > I would sure appreciate them trying to explain it to me! > > Leslie To help out on this explanation, after a fine posting regarding inductive effects a the beginning part of the above quote, I'll add the following comments. It is the carboxylate *anion* (the anion resulting after the proton is lost) that is stabilized by resonance. Thus, since it is this anion that is stabilized by resonance, the carboxylic acid is more "willing" to give up its proton to form the anion than were the anion not stabilized by resonance (as is the case with the conjugate base of an alcohol, i.e. an alkoxide). In comparing relative acid strength one compares the relative stability of the species that result after the proton is donated (i.e. the conjugate base). I hope that helps. 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 Feb 26 07:30:37 1997 Received: from jason03.u.washington.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id HAA04751; Wed, 26 Feb 1997 07:30:36 -0800 Received: from homer04.u.washington.edu (homer04.u.washington.edu [140.142.76.11]) by jason03.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with ESMTP id HAA18244 for ; Wed, 26 Feb 1997 07:24:57 -0800 Received: from localhost (fryhle@localhost) by homer04.u.washington.edu (8.8.4+UW96.12/8.8.4+UW96.12) with SMTP id HAA28744 for ; Wed, 26 Feb 1997 07:28:00 -0800 Date: Wed, 26 Feb 1997 07:28:00 -0800 (PST) From: Craig Fryhle To: Organic Chemistry I List Subject: Learning Group Problem, Ch 4 Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Learning Group Problem - Chapter Four Draw the structure of sec-butylcyclohexane in both a condensed structural formula and a bond line formula. Provide another acceptable IUPAC name for this compound. Draw the structure in its lowest energy chair conformation. Show all hydrogens on the ring, and label all the positions as being axial or equitorial. Devise at least six syntheses for sec-butylcyclohexane starting with alkyl halides (cyclic, acyclic, vinyl, or alkenyl). Make each synthesis as different from every other of the six as possible (within reason). Approach the problem by first showing the retrosynthetic pathway for each route. For the synthetic (forward direction) show all steps and reagents (not mechanisms). Be sure to employ examples somewhere in your six syntheses that use each of the three reaction types presented in section 4.15 (A. hydrogenation of alkyl halides, B. reduction of alkyl halides, and C. lithium dialkylcuprate reactions). Include carbon-carbon bond forming steps in at least four of the syntheses. lgp4-97.doc ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ Craig B. Fryhle, Ph.D. Office 206-535-8314 FAX 206-536-5055 Associate Professor Email fryhle@u.washington.edu Department of Chemistry URL http://rainier.chem.plu.edu/fryhle.html Pacific Lutheran University Tacoma, Washington 98447 ^ ^ ^ ^ ^ ^ ^ ^^^ ^^^^^^^ ^ ^^^ ^^^^ ^^^ ^ ^^^^^^^^^ ^^^^^^^^^ ^^^^^^^^^^^^^^^ ^^^^^^^^ ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ From fryhle@u.washington.edu Wed Feb 26 21:55:06 1997 Received: from jason03.u.washington.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id VAA12649; Wed, 26 Feb 1997 21:55:06 -0800 Received: from homer32.u.washington.edu (homer32.u.washington.edu [140.142.70.19]) by jason03.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.02) with ESMTP id VAA19280 for ; Wed, 26 Feb 1997 21:49:25 -0800 Received: from localhost (fryhle@localhost) by homer32.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.02) with SMTP id VAA38898 for ; Wed, 26 Feb 1997 21:52:29 -0800 Date: Wed, 26 Feb 1997 21:52:29 -0800 (PST) From: Craig Fryhle To: Organic Chemistry I List Subject: List Configuration Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings, all. A number of you had wondered why you weren't receiving messages from the list over the last few days. Apparently, when I set up the archive for the list at the end of last week a configuration also got changed that booted any user whose account did not properly receive mail, e.g. if someone's disk quota was full. Pepper, the main PLU email computer, also apparently had some unrelated but concurrent problems over the weekend that might have affected whether you got email or not. So, about 28 people were bumped automatically from the list. I have since resubscribed all of you that got bumped and changed the configuration so that you will not automatically get bumped again next time one of the organic1 messages can't get through to you. I will still get error messages every time your disk quota is full, but you will not get bumped. Please keep up with your house cleaning, though. I will appreciate it. 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 larsenak@plu.edu Thu Feb 27 11:10:31 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id LAA17711; Thu, 27 Feb 1997 11:10:31 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFWPPLB134001SL5@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 27 Feb 1997 11:07:52 PST Date: Thu, 27 Feb 1997 11:07:52 -0800 (PST) From: larsenak@plu.edu Subject: lab 6 To: organic1 Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII On the lab yesterday, the lab closed right after I finished the reflux of the isopentyl alcohol, acetic acid, and sulfuric acid. I had to leave it overnight after this. I did not have time to do the workup by adding the sodium bicarbonate. I was wondering if leaving it overnight like that would damage my product. AL From gigraykc@plu.edu Thu Feb 27 12:23:35 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id MAA18157; Thu, 27 Feb 1997 12:23:35 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFWSA3OW7O0020EK@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 27 Feb 1997 12:20:54 PST Date: Thu, 27 Feb 1997 12:20:53 -0800 (PST) From: gigraykc@plu.edu Subject: Re: lab 6 In-reply-to: To: larsenak@plu.edu Cc: organic1 Reply-to: gigraykc@plu.edu Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Even though you left your lab overnight the product should not be damaged if you finished the initial reflux. After the initial reflux was a stopping point inticated by professor Fryhle in his e-mail about lab 6. If you had added the sodium bicarbonate than the product would have possibly been damaged. I hope that this helps you out. Kelli Gigray On Thu, 27 Feb 1997 larsenak@plu.edu wrote: > On the lab yesterday, the lab closed right after I finished the reflux of > the isopentyl alcohol, acetic acid, and sulfuric acid. I had to leave it > overnight after this. I did not have time to do the workup by adding the > sodium bicarbonate. I was wondering if leaving it overnight like that > would damage my product. > AL > > From buchanbr@plu.edu Thu Feb 27 14:13:14 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id OAA18934; Thu, 27 Feb 1997 14:13:13 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFWW41BXCY001UVW@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 27 Feb 1997 14:10:33 PST Date: Thu, 27 Feb 1997 14:10:32 -0800 (PST) From: Brook Buchanan Subject: Lab 6 To: Organic Chemlist Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII When I was distilling my product at the end of the lab, all of my product boiled off and I was left with no distilled product. Did I heat it too fast or something? Also, did anyone find that using the centrifuge after adding the sodium bicarbonate gave them better results? Brook From fryhle@u.washington.edu Thu Feb 27 15:55:24 1997 Received: from jason04.u.washington.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) id PAA19455; Thu, 27 Feb 1997 15:55:23 -0800 Received: from homer34.u.washington.edu (homer34.u.washington.edu [140.142.77.15]) by jason04.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.02) with ESMTP id PAA19690; Thu, 27 Feb 1997 15:51:20 -0800 Received: from localhost (fryhle@localhost) by homer34.u.washington.edu (8.8.4+UW96.12/8.8.4+UW97.02) with SMTP id PAA16382; Thu, 27 Feb 1997 15:52:45 -0800 Date: Thu, 27 Feb 1997 15:52:45 -0800 (PST) From: Craig Fryhle To: Organic Chemistry I List cc: Chemistry Faculty -- Duane Swank , Sheri Tonn , Dean Waldow Message-ID: MIME-Version: 1.0 Content-Type: TEXT/PLAIN; charset=US-ASCII Greetings, Chem 234 Organikers. There is a demonstration set up for the initial distillation on the demo bench in the Open Lab. We will use a 50 mL RB flask for the cloves and water instead of a 25 mL. Assemble your apparatus as shown on the demo bench. Use heating mantle and Variac for the heating device, not an aluminum block. The heating mantles are in the green cabinets by the organic dispensing hood. The ceramic well doesnt have to fit the 50 mL round bottomed flask exactly - the well can be a little larger if the perfect size is not available. THIS TIME we will omit the thermometer from the top of the distillation apparatus and simply plug that opening with a stopper, since it is principally water that you are distilling. If the temperature were to be measured it would be just below 100 C, not at all reflective of the bp of clove oil, so there is no need for the thermometer there. Id suggest that you read in your lab text about steam distillations. By type, a steam distillation is a form of co-distillation involving immiscible liquids, which in this case are water and eugenol. So instead, put the thermometer in the aluminum block to guage your hot plate setting. The amount of clove oil obtained is very small. In order for you to have some to turn in for grading you have to pay attention to a couple of things. When you are at the step of evaporating the methylene chloride (CHCl2), transfer the methylene chloride solution to your *tared* sample grading vial and evaporate the methylene chloride from that container. This way your product is already in the vial you need it to be in for grading when the solvent has finished evaporating. Note the bp of methylene chloride. Very mild heat and a very gentle flow of air should be sufficient to evaporate the methylene chloride during this step. When there is still methylene chloride present the solution will not be very viscous at all. When the methylene chloride is gone the clove oil will be just that, a slightly viscous oil. If there are what appear to be oily droplets let reminaing after you have evaporated the methylene chloride (two phases are apparent), it is probably water that you did not adequately remove during the drying (Na2SO4) step. If so, add back some fresh methylene chloride and repeat the Na2SO4 and evaporation steps, being sure to exclude water from the all containers. About percent yield. The notion of percent yield in the stoichiometric sense is not applicable. Instead, what is relevant is a percent recovery, based on the initial weight of cloves used, since no reaction was conducted and it is simply a matter of how much eugenol you got from a given amount of cloves. Contrary to the syllabus this year, you can omit interpretation of the IR and NMR spectra of eugenol. 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 velezsa@plu.edu Thu Feb 27 17:28:43 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id RAA20091; Thu, 27 Feb 1997 17:28:42 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFX2XF7KUO002IHE@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 27 Feb 1997 17:26:01 PST Date: Thu, 27 Feb 1997 17:26:01 -0800 (PST) From: velezsa@plu.edu Subject: lab 6 To: "org. chem list" Cc: brook Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII brook, your product didn't boil off. It was in the distiller. If you had anything left in the conical vial it was impurities. --Stephanie From velezsa@plu.edu Thu Feb 27 17:40:28 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id RAA20194; Thu, 27 Feb 1997 17:40:27 -0800 Received: from plu.edu by plu.edu (PMDF V5.1-5 #17589) id <01IFX3BR1Y1Y002E5Y@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 27 Feb 1997 17:37:34 PST Date: Thu, 27 Feb 1997 17:37:33 -0800 (PST) From: velezsa@plu.edu Subject: group 17 To: "org. chem list" Message-id: MIME-version: 1.0 Content-type: TEXT/PLAIN; charset=US-ASCII Where are you? I lost your phone numbers and we need to get together. --Stehanie From baileyle@plu.edu Thu Feb 27 21:37:08 1997 Received: from pepper.PLU.edu by rainier.chem.plu.edu via ESMTP (950413.SGI.8.6.12/930416.SGI) for id VAA21641; Thu, 27 Feb 1997 21:37:08 -0800 Received: from Hind215b.PLU.EDU by plu.edu (PMDF V5.1-5 #17589) with SMTP id <01IFXBL7P7MS002E66@plu.edu> for organic1@rainier.chem.plu.edu; Thu, 27 Feb 1997 21:34:15 PST Date: Thu, 27 Feb 1997 21:32:25 -0800 From: Lora Bailey Subject: group 2! To: organic1 Reply-to: baileyle@plu.edu Message-id: <33166DE9.2295@plu.edu> MIME-version: 1.0 X-Mailer: Mozilla 3.01 (Win95; I) Content-type: text/plain; charset=us-ascii Content-transfer-encoding: 7bit Hey, don't forget to let me know when you guys want to meet on Sunday. I won't be here to check my voicemail, but I can check my email from home. Thanks, Lora