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Why do acetone and acetaldehyde prefer to exist overwhelmingly in the keto rather than the enol form?
I do not want a negative answer, such as that their enols lack conjugation with other double bonds, or that their enols lack six-membered ring chelation like acetoacetic esters.
I want a positive explanation of why it is natural that acetone exists most of the time as 2-propanone and not 2-propenol.
1 Answer
- L. A. L.Lv 61 decade agoFavorite Answer
Generally, because the resonance favors the keto bond.
Oxygen is more electronegative than carbon, so the C=O bond is stronger than the C-OH and the C=C bonds. Hence the keto form is more likely to be present at any given moment.
ADDED LATER
I was asked what we were talking about...guess that was not clear :-))
The keto/enol resonance eq for acetone is
CH3C(=O)CH3 <<<---> CH3C(OH)=CH2
Here you can see the structures involved...but I wish we cd draw more realistic diagrams on this site :-((
