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| Ian R Gould >igould@asu.edu | CHM 234:General Organic Chemistry II > Spring 2012 |
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| Home | Lecture Material | Problems | Assignments | Study Aids | Your Points | Course Info | Help! |
Announcements (hit the Refresh button on your browser to make sure that you are seeing the latest version of this page, and every other page on this website)
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Feb 15, 2012 I was asked for some practice mechanism problems that involved ring making/breaking/expansion/contraction. I thought this was a good idea and so I have collected together some mechanism problems and pout them on the problems page, click HERE. More... |
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Feb 13, 2012 Today's lecture has been posted. To see the small movie on the Diels-Alder reaction I showed in class today, click HERE. More... |
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Feb 13, 2012 The answer key to Quiz #5, and a new Quiz #6 have been posted. The deadline for quiz #6 is 11:59PM, Sunday Feb. 19th. More... |
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Feb 12, 2012 The Weekly Work page of suggested problems has been updated for week #7, including a new set of problems from the Retrosynthesis teaching site. More... |
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Feb 12, 2012 Then results for the first midterm have been posted. The tests will be returned in class tomorrow, Feb 13, or they can be picked up any office hours. More... |
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Feb 10, 2012 I just redid the Ethers/Epoxides Reactions Problem page. It no longer looks like the one in your notes, it is significantly expanded. If you have already done this page you might want to go back and try some of the new problems. More... |
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Feb 10, 2012 Homework website update: We have found that there is a browser specific problem with recording the credit, AND a browser dependent problem logging into the website. Firefox works bit some other browsers don't, and it seems to be irreproducible. This should not be your problem, obviously, and so until it is fixed you can ignore the credit issue, ALL students will receive all credit until this problem is fixed. We are working on logging in problem right now. Apologies for all the problems! UPDATE Feb 11th: The login problem has now (hopefully) been fixed, please login using your last name, ALL LOWERCASE, and you posting ID. If there are any remaining login problems, please let me know asap. Now working on the report problem! |
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Feb 10, 2012 There will be NO review session on Saturday, we haven't covered enough material since the last midterm and I will be grading. However, I will have office hours at the usual time 4 - 5PM in my office. The quiz this week is due SUNDAY at 11:59PM. |
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Feb 8, 2012 Several students who did not take my CHM 233 class had asked for some review material on Reaction energy/coordinate diagrams. I obviously think that these are very important because they describe everything about a reaction. I have finally finished some review material, you will find it on the CHM 233 Review page on this website. There you will find a review lecture, some gapped notes to go along with the lecture and some practice problems to aid your learning of this important subject. Reaction energy diagrams are now considered fair game for any test the rest of this semester! More... |
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Feb 8, 2012 Thanks to the efforts of your classmate Phivu Nguyen, who recompiled all of the lectures into .mp4 format, all of the CHM 233 lectures are now available for download, click HERE. More... |
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Feb 7, 2012 Thee Weekly Work page of suggested problems has been updated for week #6, including a new set of problems from the Retrosynthesis teaching site. More... |
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Feb 7, 2012 A new Quiz #5 has been posted. The deadline is 11:59PM, Sunday Feb. 12th. More... |
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Feb 8, 2012 Your scores for Quizzes 2 - 4 have been posted on the Your Points page. Please make sure that your quiz scores are recorded correctly. This year there is 1/2 point for each question, rounded UP, so be careful, if you got 6 points (which is the maximum), you may still have got one of the questions wrong due to the rounding up. Same goes for 5 points, you may have 3 wrong etc., so it is important that you check the quiz answer key to make sure you know what you got right and what you got wrong. More... |
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Feb 6, 2012 Question 6 was missing from the midterm, it was the Conceptual Question and I accidentally deleted it when I made the test for copying. It was worth 5 points. I will give the entire class these 5 points. If you are interested, this is what it was supposed to be: Question 6 (5 pts.) An alkyne reacts slower than an alkene in an electrophilic addition reaction because.... the electrons in the pi-bonds are lower in energy in the alkyne because the sp hybridization results in a shorter C-C bond and better overlap between the 2 sets of p atomic orbitals |
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Feb 5, 2012 I have been asked to provide some review material related to reaction energy diagrams for this students who did not take my class last semester. I finally got around to doing that today, but it is a bit late for midterm #1, so, there will be no energy diagrams on the test tomorrow. I will post the review material next week after the test. Look for energy diagrams on subsequent tests. |
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Feb 5, 2012 The answer key to Quiz #4 has been posted. More... |
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Feb 5, 2012 There is now a page of concept questions/statements, one of which will be taken directly and put onto midterm #1. To see this list, click HERE. There was an important typo in the answer to #3, so if you downloaded the pdf file before noon Feb 5th you will have an error there, it is supposed to say: the new sigma-bonds formed in the ALKYNE addition reaction are to carbons that are sp2 hybridized (makes stronger bonds) compared to sp3 hybridized in addition reactions to alkenes |
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Feb 4, 2012 HOMEWORK PROBLEMS. Well, we have been having a lot of problems trying to get the homework website working, and I am sure there are still some bugs. Nevertheless, it is supposed to help you to learn retrosynthesis, and so I decided to get it put at the last minute to see if it might be helpful for the first midterm. You will get credit for using this site. You do not earn credit for getting any problem correct, indeed there is no way to input answers anyway. You earn credit just by LOOKING at each problem as appropriate. If you just look at the problem and then get out of the system you will earn as much credit as if you work through each problem in detail. I am not yet sure how much credit will be available this semester, but it will be normalized to a maximum of 40 points at the end of the semester. You need to login to the system so that we can assign credit as appropriate. This website is also part of a chemical education project that we are running and when you logon for the first time you will be asked if you would like to participate or not. If you do, we will track the way that the the participants use the website to see if there is any correlation with their performance on retrosynthesis problems. Your participation will be anonymous, we do not track individuals, we only look for class-wide trends. You earn no extra credit for participating, there are no penalties for not participating. Obviously we need as many of you as possible to participate to make the study meaningful. There may be some bugs left in the system if there are I apologize, we will fix them next week, but I just wanted to get this out before the midterm. Thanks for your understanding. To access the website, go to retro.asu.edu. Although the problems are on a website, and you will interact with the site, you are supposed to be working the problems out on a piece of paper as you go. UPDATE: the login system is not working correctly, try to login using your FIRST name, all lowercase, not your last name as in the instructions. if that does not work then enter "gould" as your name (all lowercase) and then enter 1111111 as your posting ID. Apologies for the inconvenience! Everybody will earn the appropriate credit for these problems despite the login problem! |
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Feb 4, 2012 Today's review session has been posted. Later this evening I will post the promised homework problems that were delayed, probably late tonight. More... |
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Feb 4, 2012 The following is a list of mechanisms that are in the 2ND semester notes so far that you do NOT have to know for the next midterm: 1) Radical addition of HBr to an alkyne (p 8 alkyne notes) 2) Reaction of (Sia)2BH.THF and -OH/H2O2 with an alkyne (p 10 alkynes notes) 3) Reduction of an alkyne using Na/NH3(l) (p12 alkynes notes) 4) Oxidation of primary and secondary alcohols using Na2Cr2Oseven/H2SO4/H2O, but you DO have to know the mechanism for formation of the hydrate from the aldehyde (p 8, 9 alcohols notes) 5) Reaction of alcohols with PBr3 (p 12 alcohols notes) 6) Reaction of alcohols with SOCl2 (p 12 alcohols notes) Anything else is fair game |
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Feb 2, 2012 To see a list of known errors in problems et #1, click HERE. More... |
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Feb 2, 2012 Today's review session has been posted, the subject was nomenclature, acidity, substituent effects and reactions. The review session on Saturday will cover synthesis and mechanisms. In the review session I made an error, I said that when naming a structure with multiple functional groups that contains an alkyne, and alkene and an alcohol, I said that the order the functional groups are arranged in the name is -yne then -ene then -ol, when in fact it should have been -ene followed by -yne followed by -ol. So, the name of the 3rd structure that we named in the review session at 8:30 mins should have been (6S)-bromohept-(4E)-en-1-yn-(3R)-ol, NOT as given in the recording, (6S)-bromohept-1-yn-(4E)-en-(3R)-ol, sorry! Thanks to the student who spotted that error! More... |
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Feb 1, 2012 Thee Weekly Work page of suggested problems has been updated for week #5 (a little late I am sorry). More... |
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Feb 1, 2012 My completed version of the Organometals notes has been posted on the Lecture Material page. Please use this to make sure that your notes are up to date and have no errors, thanks. THIS REPRESENTS THE END OF THE MATERIAL FOR THE FIRST MIDTERM, THE TEST COVERS EVERYTHING UP TO AND INCLUDING GRIGNARD AND ORGANOLITHIUMS DISCUSSED IN CLASS TODAY. On Friday we will finish a few more synthesis problems relevant to the first midterm, and continue into the notes for the second midterm. More... |
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Jan 30, 2012 My completed version of the Alcohols notes has been posted on the Lecture Material page. Please use this to make sure that your notes are up to date and have no errors, thanks. More... |
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Jan 30, 2012 The ' to Quiz #3, and a new Quiz #4 has been posted. The submit deadline for the quiz this week is SATURDAY Feb 4th! More... |
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Jan 29, 2012 Midterm #1 is coming up next week, Monday Feb. 6th! Regular/onground class students will take the test in LS A-191. Online/hybrid class students will take the test in PS H-150. This weeks quiz #4 will be due SATURDAY FEB. 4th so that I can post the answer key as a study aid on Sunday. There will be TWO review sessions. The first will be Thursday evening, Feb. 2nd, 6 - 8PM in PS H-150. The second will be Saturday Feb. 4th, 4 - 6PM again in PS H-150. Both will cover different material and both will be recorded. To see a summary of all of the reactions you will need to know for midterm #1, click HERE. Please read the study advice on the first page of this summary. Do NOT start to study by trying to memorize these reactions. Work as many problems as you can that use these reactions and then go back to this list to help you memorize whatever parts you have not yet learned. Some memorization will be inevitable this semester as we learn a lot of new reagents. Yes, I know, this list is long.... When it comes to the memorization part, follow the advice given in the video given in the study advice page, click HERE. As you can see, in previous years I expected you to make your own list of reactions, this year I have already provided the list for you, you do not need to make your own. What mechanisms do you ned to know? You will not be able to "learn" all of the mechanisms that you need to know this semester because I will be asking you to write mechanisms for reactions you have not seen, so there is no "list" of mechanisms to be memorized. Of course, some mechanisms will come from the notes, and for advice on how to handle those, click HERE. In general I ask mechanisms for reactions that involve standard Lewis acid/base steps that occur in multiple mechanisms. Use the problem set as a guide here. What else do you need to know? Conceptual stuff and nomenclature, click HERE. Also, synthesis problems, see the weekly work pages for many problems, the the problems set and also the teaching website that will be released this week (look for announcements in class and on this site). Finally, I will also be asking spectroscopy problems, but probably not on every midterm, but they will be similar to those on the problem set, i.e. fairly straightforward. |
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Jan 29, 2012 Problem Set #1 has been posted, use it to prepare for midterm #1. More... |
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Jan 28, 2012 Today's review session has been posted, the subject was substituent effects and alkyne synthesis. At the end of the review session I left the students with some problems to solve on their own. To see these problems and my answers, click HERE. More... |
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Jan 28, 2012 There will be a review session TODAY in LS A-191, 4 - 5PM, the subject will be synthesis using alkyne C-C bond-forming reactions and, apparently, substituent effects on benzene rings. It will be recorded as usual. |
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Jan 28, 2012 I was asked a question about substituent effects on benzene, pacifically -NH2 as an example. My answer may be useful to the whole class for a moment let's ignore the acidity of phenols and only talk about benzene rings and substituents when connected to a benzene ring, a -NH2 will actually donate electrons into the ring, and this can be illustrated by drawing a minor resonance contributor that would have a positive charge on N and a negative charge on one of the carbons on the benzene ring think back to first semester when we explained chemical shifts for protons on benzene rings with substituents by drawing resonance contributors in this way, e.g. here at ca. 21 minutes: http://www.asu.edu/courses/chm331/lectures/l22/l22.html when we do the chemistry of benzene rings we will find that these effects are very important so, ignoring the acidity of phenols for a moment, when e.g. -NH2 donates into a benzene ring it raises the energy of the electrons in the benzene ring which makes the benzene ring more reactive (higher energy electrons) in the kinds of reactions that it does, which are to come it doesn't stabilize the benzene ring by resonance because it is actually adding electron density into the ring it would be different if there were a positive charge on the ring, but we will discuss that later now back to phenol acidity and the conjugate base anions that arise from deprotonation without a -NH2, the electrons are delocalized into the ring, which actually stabilizes them a bit, so far so good with the -NH2 the electrons are delocalized into the ring, BUT, the ring electrons are already higher in energy because of the donating effect of the -NH2, and so they don't gain as much benefit from delocalization into the ring as they would have if the -NH2 was not there, OR, another way to look at it is that one of the resonance contributors has the non-bonding electrons on the carbon which as the N attached, then the two pairs of non-bonding electrons repel, raising the total energy, this was the explanation given in class this electron raising effect overwhelms any inductive stabilizing effect due to the electronegative nitrogen |
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Jan 26, 2012 My completed version of the Alkynes notes has been posted on the Lecture Material page. Please use this to make sure that your notes are up to date and have no errors, thanks. More... |
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Jan 26, 2012 I have been asked about what reactions from first semester organic chemistry you will need to know for the first midterm in CHM 234, specifically if you need to know any of the reactions from the "cheat sheet" you were given on the final. The first semester reactions you need to know are summarized on the first set of problems for CHM 234 on the Problems poge, click HERE. The only reaction on this page of problems that was also on the "cheat sheet" is formation of an epoxide using MCPBA, the others on the cheat sheet we will not use in 234 except for hydrolysis of an epoxide to give a diol, which you won't have to know for midterm #1 because we will cover it again for midterm #2. |
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Jan 23, 2012 Here is an important announcement about a study being conducted by the School of Social and Family Dynamics at ASU Many talented Latino teenagers are turning away from science classes and careers. We want to help develop programs that will support high school students in science. We would like to invite Latino ASU students to attend a focus group. Participants will be asked to (1) provide feedback on surveys and (2) talk about what helped you get this far in science. Participants will receive $25 in cash. Focus groups will last no longer than 2 hours and will be held on the ASU Tempe campus. If you are interested in learning more, please visit the following url to complete a short interest form (1-2 minutes): www.surveymonkey.com/s/Families_and_Science. For more information, please contact: Chara Price Graduate student chara.price@asu.edu or Dr. Sandra Simpkins Associate Professor Sandra.simpkins@asu.edu |
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Jan 23, 2012 The answer key to Quiz #2, and a new Quiz #3 has been posted. More... |
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Jan 22, 2012 the Weekly Work page of suggested problems has been updated for week #4. More... |
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Jan 22, 2012 A student noticed that at 45:15 in the lecture on Jan 18th I said that I need you to know that alkynes react faster than alkenes. Of course, what I meant to say was that I need you to know that ALKENES react faster than ALKYNES. Oops! This will always be true if the reactions involve Lewis acid base reactions, since the energy of the electrons in the pi-bonds in alkynes are lower than the corresponding pi-electrons in alkenes, they are less reactive in a KINETIC sense, i.e. they are poorer nucleophiles). Alkyne reactions tend to be moor exothermic than alkene reactions, but that is mainly a result of the second step in the mechanism, the step that is not rate determining. Of course, this is only the case if the reactions proceed via Lewis acid/base mechanisms, for example, on the Lindlar catalyst an alkyne reduces faster than an alkene, but that is because the reaction proceeds via a very different, non Lewis acid/base mechanism. Glad someone is listening to the lectures carefully :D For a more detailed explanation, click HERE. |
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Jan 21, 2012 Today's review session has been posted, the subject was alkyne reactions/mechanisms and some synthesis problems. In the middle of the review session I left the students with some problems to solve on their own. To see these problems and my answers, click HERE. More... |
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Jan 21, 2012 There will be a review session today in PS H-150 (NOT LS A-191), 4 -5PM as usual. The topic will be more synthesis problems, incorporating some of the newer reactions. I will be available to answer questions 1-on-1 after the review. |
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Jan 18, 2012 Tomorrow evening, Thursday Jan 19th, I will hold regular office hours in my office as usual, 6 - 7PM. Then from 7PM - 8PM will hold "online" office hours for anybody who has questions and can't make it to campus. More... |
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Jan 16, 2012 the Weekly Work page of suggested problems has been updated for week #3. More... |
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Jan 16, 2012 Your scores for Quiz #1 have been posted on the Your Points page. Please make sure that you can find yourself on my roster and that you quiz score is recorded correctly. this year there is 1/2 point for each question, rounded UP, so be careful, if you got 6 points (which is the maximum), you may still have got one of the questions wrong due to the rounding up. Same goes for 5 points, you may have 3 wrong etc., so it is important that you check the quiz answer key to make sure you know what you got right and what you got wrong. More... |
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Jan 16, 2012 The answer key to Quiz #1, and a new Quiz #2 has been posted. More... |
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Jan 14, 2012 Today's review session has been posted, the subject was synthons and multi-step synthesis. At the end of the review session I left the students with some problems to solve on their own. To see these problems and my answers, click HERE. More... |
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Jan 13, 2012 There will be a review session tomorrow, Saturday Jan 14th, 4 - 5PM in LS A-191. The subject will be synthons and 1st semester reactions within the context of synthesis problems. I will be available to talk to students 1-on-1 after the review. |
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Jan 13, 2012 Quiz #1 can now be submitted. More... |
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Jan 13, 2012 Lecture #4 has been posted in the recorded lectures page. Online/hybrid students will need to register to watch this lecture before they can submit Quiz #1. This is the last time that a lecture posting will be included on this main announcements page, from now on please just go straight to the recorded lectures page. More... |
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Jan 11, 2012 If you are interested in doing an honors project for this class, there are two opportunities. The first involves mentoring some Kino Jr. High kids who will be putting together some science fair projects that they hope to take to the state competition. This is very important opportunity for the Kino kids and a very worthy project. However, time is critical for this project because they have started work already and we would need you to start straight away. The second project involves answering science questions same as last semester. More... |
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Jan 11, 2012 At the request of a student I have added a download link to each of the recorded lecture files so that they can be watched offline. Let me know if there are any problems with this or if you think it is useful. The lecture files are mainly .swf (flash) files, that can be opened in just about any browser (but without the controls). However, I just realized that so far this semester I have accidentally been making .mp4 files, which are a lot larger. So lectures 1 - 3 are .mp4, the rest will be .swf. (I could go back and recompile 1 - 3 but I am feeling lazy today!) More... |
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Jan 11, 2012 My completed version of the Retrosynthesis notes has been posted on the Lecture Material page. Please use this to make sue that your notes are up to date and have no errors, thanks. More... |
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Jan 11, 2012 Lecture #3 has been posted in the recorded lectures page. This is the last lecture that the online/hybrid students will not have to register to watch. Online/hybrid students will need to register to watch lecture #4 (Friday) before they can submit Quiz #1. More... |
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Jan 9, 2012 the Weekly Work page of suggested problems has been updated for week #2. More... |
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Jan 9, 2012 Here s the information regarding the SI sessions that were mentioned in class this morning: SI Leader = Molly Downey email: molly.downey@asu.edu Session Times: Sundays 12-1 pm in Hayden C-52 Mondays 7-8 pm in LSA 109 Wednesdays 1-2 pm in Hayden C-52 There will be an Ochem SI facebook page coming soon |
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Jan 9, 2012 Lecture #2 has been posted on the Lectures page. Online/hybrid students do not have to register to watch this lecture, registering for lectures will start with #4. More... |
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Jan 7, 2012 Today's review session has been posted, the subject was fundamental Lewis acid/base reactions and mechanisms. The end of the review session had a couple of mechanisms including a tricky mechanism that you might want to try to practice solving even if you are familiar and comfortable with first semester mechanism concepts. Start at minute 47 for the first of these and start at minute 59 for the second harder one. More... |
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Jan 6, 2012 I have office hours every Saturday, this semester from 4PM - 5PM. Usually these take the form of a review session, however. I am always available to talk to students 1-on-1 at the end of the review. The first Saturday office hours/review session will be TOMORROW, Jan 7th, 4 - 5PM, in LS A-191. The subject will be 1st semester mechanisms. This is PRIMARILY for students who did not take my Fall 2011 CHM 233 class (although everybody is welcome to attend). I need to make sure that we all understand how I like to see mechanisms drawn. The review session will be recorded just like the lectures and posted on the class website. |
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Jan 6, 2012 Lecture #1 has been posted on the Lectures page. I will usually not post an announcement on the main webpage when lectures are posted. They are usually posted the same morning that the lecture is delivered in class, unless I get busy of have a meeting or something similar, however, they should always be posted the same day. Online/hybrid students do not have to register to watch this lecture, registering for lectures will start with #4. More... |
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Jan 3, 2012 Welcome to CHM 234, General Organic Chemistry II, Spring 2012. The syllabus/procedures for this class are very similar to CHM 233, Fall 2011. Because most students have already heard all of this, I will not be going over this again on the first day of class, instead I have posted this information in the form of a recording, click HERE. There is also a recording specifically for this students in the online/hybrid version of the class, click HERE. There is also a recording specifically for those students who did not take my CHM 233 General Organic Chemistry I class in Fall 2011, click HERE. Finally, there is also a recording that shows how to use the class website, click HERE. Click here for Syllabus for the Regular Onground Class : SLN 10316 (pdf file) Click here for the Course Schedule for Both Classes (pdf file) Click here for Syllabus for the Online/Hybrid Class : SLN 20658 (pdf file) |
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Jan 1, 2012 Quiz #1 has been posted. You will not be able to submit the quiz until 9AM Friday January 13th, i.e. after the drop/add deadline and after I have had time to setup my roster. The deadline for Quiz #1 will be 11:59PM, Sunday Jan. 15th. More... |
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Jan 1, 2012 This class uses "gapped" lecture notes that you complete in class. They are available as pdf files under the Lecture Material tab. You can print these and bring them to lecture, or you can save money by purchasing the entire notes set from The Alternative Copy Shop, at the southwest corner of Mill Ave. and 10th street. The cost should be ca. $30, give them a call before you go to make sure that they have some copies in stock (480) 829-7992. They should be available for pickup on Wednesday January 4th, but check before you go. I will distribute gapped notes in the first class that will last the first two lectures. You can also get the notes for these first lectures by printing the first seven pages of the "Retrosynthesis" notes, click HERE. More... |
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Jan 1, 2012 The recommended textbook for this class is Organic Chemistry, 3rd Edition, by J.G. Smith. If you use the textbook it is critical that you also get the accompanying Solutions Manual, since the problems are the MOST IMPORTANT part of the textbook. To keep costs down for students, we have negotiated two special paperback Textbook/Solutions Manual packages, one for CHM 233 and one for CHM 234, that are available at the ASU bookstore. The cost of the ASU special packages is probably lower than you will be able to find elsewhere for a Textbook/Solution Manual combo. If you get a 3rd Edition textbook somewhere else, please make sure that you also get the Solutions Manual. The ASU special editions do not include chapters on topics such as proteins, nucleic acids, carbohydrates etc. These topics are not covered at ASU because we aim to teach the best organic chemistry course possible, and this will not include a superficial overview of biochemical molecules. To understand biochemical molecules properly you will need to take a biochemistry course. I will provide suggested reading and problems from the 3rd Edition of Smith ONLY. I will not be able to suggest reading or problems from any earlier edition of Smith, or from any other textbook. If you have any other textbook, it should be fairly easy for you to find the appropriate reading and problems yourself. The Textbook is recommended, not required. Many students will ask me if they should buy the textbook. Unfortunately I am not able to give a satisfactory answer, since different students have very different needs. Some students really need to study from a textbook and appreciate the chance to read about a topic from a perspective that is different from that of the instructor. Also, some students want a permanent textbook to study for the MCAT, for example. Some students will not need a textbook at all, since there is a lot of learning material on the class website. It is also true that you can learn most of what you need to know from just about any organic textbook. You have to make your own decision on this I am afraid! Note that the lab is a separate course, the textbook for the lab course is REQUIRED! |
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Jan 1, 2012 It is not possible for me to give an override into this class since I am not allowed to override the reserved seat assignments or the room capacity. If you really want to get into this class, come during the first week and be persistent in trying to register online. There will be a lot of drop/add activity during the first week, persistence usually pays off. Remember that the class is offered both in the regular onground lecture format (SLN 10316) and also as an online/hybrid version (SLN 20658). Both classes are basically identical. If you are registered for the online/hybrid class you are welcome to attend lecture with the regular class. |
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