Cyclohexanone and Enol C6H10O

Section 22-2. Keto-enol tautomerism.

Enols are tautomers of carbonyl compounds, meaning that they are related to each other by the movement of a hydrogen atom and a double bond. Where the carbonyl compound has the atom structure -CH-C=O, the enol has the structure -C=C-OH. Although at first sight there would appear little to choose between the stabilities of these two structures, it turns out that the carbonyl double bond is stronger (and so lower energy) than the C,C double bond, attributable in part to the polarity of the former. Look at these two structures and note the differences between them. In an equilibrium between the two, cyclohexanone is 99.99% ketone, and only 0.01% enol.


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File created Sun Aug 4 01:51:03 2002