When we have discussed the enol-keto tautomerization of ketones in class, the isomerization has been facililated by an acid or base catalyst, with most ketones heavily favoring the carbonyl isomer at equilibrium. However, samples of the ketone below in its pure form (with no acid, base or water present) contain nearly 10% of the enol form! HO, -90% ~10% From this data, we can infer that the enol isomer of this ketone is particularly stable. Explain the stability of this enol, using terms and ideas that we have discussed in this unit.
When we have discussed the enol-keto tautomerization of ketones in class, the isomerization has been facililated by an acid or base catalyst, with most ketones heavily favoring the carbonyl isomer at equilibrium. However, samples of the ketone below in its pure form (with no acid, base or water present) contain nearly 10% of the enol form! HO, -90% ~10% From this data, we can infer that the enol isomer of this ketone is particularly stable. Explain the stability of this enol, using terms and ideas that we have discussed in this unit.
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter10: Alcohols
Section: Chapter Questions
Problem 10.52P: Alcohols are important for organic synthesis, especially in situations involving alkenes. The...
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