Both 2,4-pentanedione and ethyl acetoacetate have two carbonyl groups separated by a

Chapter 23, Problem 23.31

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Both 2,4-pentanedione and ethyl acetoacetate have two carbonyl groups separated by a single carbon atom. Although an equilibrium mixture of 2,4-pentanedione tautomers contains 76% of the enol forms, an equilibrium mixture of ethyl acetoacetate tautomers contains only 8% of the enol forms. Suggest a reason for this difference. OCH2CH3 2,4-pentanedione ethyl acetoacetate O O O O

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