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How to know equilibrium direction for keto-enol tautomerisms?
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James Tomlinson
How to know equilibrium direction for keto-enol tautomerisms?
It seems to me that you are asking two separate (although not entirely unrelated questions). One, what governs the equilibrium in ketone-enol tautomerizations. Two, why are 1,3-dicarbonyls more acidic than say 1,4 dicarbonyls. The second question involves the potential loss of a proton and is governed by the pKa, but the first question does not imply the loss of a proton. Is that correct?
It seems to me that you are asking two separate (although not entirely unrelated questions). One, what governs the equilibrium in ketone-enol tautomerizations. Two, why are 1,3-dicarbonyls more acidic than say 1,4 dicarbonyls. The second question involves the potential loss of a proton and is governed by the pKa, but the first question does not imply the loss of a proton. Is that correct?
Exactly, I mean, I see an enol formed in both cases with the loss of one proton. Why does the flanking of the alpha hydrogen by two carbonyl groups make it that much more likely for an enol to form, relative to a molecule that has only a single carbonyl group?
Exactly, I mean, I see an enol formed in both cases with the loss of one proton. Why does the flanking of the alpha hydrogen by two carbonyl groups make it that much more likely for an enol to form, relative to a molecule that has only a single carbonyl group?
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