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stability of 4-tert-butylcyclohexanone confermers
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Topic: stability of 4-tert-butylcyclohexanone confermers (Read 3844 times)
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llagetias
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stability of 4-tert-butylcyclohexanone confermers
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November 05, 2010, 08:12:55 PM »
I got this problem wrong on my Orgo lab quiz and I want to figure out what I did wrong. According to the problem, there were four cyclohexane templates drawn and I drew two conformers, one with the substituents in the axial position and the other with the substituents in the equatorial position in a trans conformation and the other two conformers with one substituent axial and the other equatorial (cis conformers). I said the most stable conformer was the one with both subtituents in the equatorial position (trans) but my TA marked it wrong. I know that the tert-butyl group cannot be axial but am not sure what the correct answer is and why. If anyone can help me out I would really appreciate it.
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MissPhosgene
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Re: stability of 4-tert-butylcyclohexanone confermers
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November 05, 2010, 10:33:55 PM »
Could you provide a scheme?
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Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.
macman104
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Re: stability of 4-tert-butylcyclohexanone confermers
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November 06, 2010, 02:36:19 PM »
Could they have marked it wrong because they were not looking for the carbonyl to be drawn axial or equatorial, but more "planar" looking? I can't post chemdraw right now otherwise I would show what I mean.
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llagetias
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Re: stability of 4-tert-butylcyclohexanone confermers
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November 09, 2010, 11:56:37 PM »
I can scan the quiz in tomorrow (or ask my TA, either way), but I think the main problem was I drew the structure wrong. Also in my class, they were talking about the Felkin Ahn model and that might have had something to do with the answer.
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stability of 4-tert-butylcyclohexanone confermers