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Subject:
Organic Mechanism
Category: Science > Chemistry Asked by: shal04-ga List Price: $15.00 |
Posted:
12 May 2004 20:49 PDT
Expires: 11 Jun 2004 20:49 PDT Question ID: 345546 |
I am having trouble with a mechanism that I am working on. The mechanism can be found here: http://www.uwrf.edu/~shalyn.r.morrow/chem Heat is added for the reaction to proceed. |
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There is no answer at this time. |
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Subject:
Re: Organic Mechanism
From: stuyshick-ga on 13 May 2004 16:38 PDT |
Dear Shal, Great question! Probably the most exciting 7 minutes of my day. Since the reaction occurs with heat alone, it seems very likely to be a Woodward-Hoffman rearrangement with 4n+2 pi electrons. Its too bad that I can't paste images here but I did post the mechanism on my school website. Check it out at: http://homepages.nyu.edu/~ms1864/ It is a concerted step reaction and the numbers in blue are only written as a suggested order but everything really happens in one step. It makes perfect sense because if you count the arrows, there are 5 of them. It is a 10 pi electron system (4n+2 where n=2) which, by woodward-hoffman rules, should go with heat (not light). Glad to help. Let me know what you think. P.S. Sorry for the crappy artwork but its the best I could get out of Paint. |
Subject:
Re: Organic Mechanism
From: acrh2-ga on 13 May 2004 18:08 PDT |
Where exactly did you find 10 pi electrons? |
Subject:
Re: Organic Mechanism
From: shal04-ga on 13 May 2004 21:58 PDT |
I am assuming that it was meant that there are 6 pi electrons, which still follows the 4n+2 rule, instead of 10. |
Subject:
Re: Organic Mechanism
From: dr_bob-ga on 13 May 2004 23:05 PDT |
sorry stuyshick, but i disagree that this is a concerted mechanism, you just don't have the orbital overlap for this to happen in a single step. Try first, a 3,3 sigmatropic shift, followed by another. |
Subject:
Re: Organic Mechanism
From: shal04-ga on 13 May 2004 23:39 PDT |
Thank you to both of you for your help! It is greatly appreciated. I was originally thinking a 3,3 shift, but could not get it to work. I think that I now have it first doing a 3,3 shift leaving the oxygen chain alone, and then after that another 3,3 shift involving the oxygen chain this time. Thanks again!!! |
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