The reason as to why the equilibrium mixture of pentane-2, 4-dione tautomers contains 76 % of the enol forms and an equilibrium mixture of ethyl acetoacetate tautomers contains only 8 % of the enol forms is to be stated. Concept introduction: .Tautomers are isomers which differ only in the position of the hydrogen and electrons of the electronegative atom, generally oxygen. There is no change in the carbon skeleton of the compound. This phenomenon which involves simple proton transfer in an intramolecular fashion is known as tautomerism.The very common example of tautomerism is Keto-enol tautomerism. It can be acid or base catalysed. The very common example of tautomerism is Keto-enol tautomerism. It can be acid or base catalyzed.

Question

The Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of formation of an enamine from a ketone, Michael addition to an α,β-unsaturated carbonyl compound, and hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between acetophenone and 3-buten-2-one. Draw the structure of the product of the enamine formed between acetophenone and pyrrolidine. Draw the structure of the Michael addition product. Draw the structure of the final product.

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Question

Chapter 23, Problem 23.32P

Interpretation Introduction

Interpretation: The reason as to why the equilibrium mixture of pentane-2, 4-dione tautomers contains 76 % of the enol forms and an equilibrium mixture of ethyl

acetoacetate tautomers contains only 8 % of the enol forms is to be stated.

Concept introduction:.Tautomers are isomers which differ only in the position of the hydrogen and electrons of the electronegative atom, generally oxygen. There is no change in the carbon skeleton of the compound. This phenomenon which involves simple proton transfer in an intramolecular fashion is known as tautomerism.The very common example of tautomerism is Keto-enol tautomerism. It can be acid or base catalysed.

The very common example of tautomerism is Keto-enol tautomerism. It can be acid or base catalyzed.

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The Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of formation of an enamine from a ketone, Michael addition to an α,β-unsaturated carbonyl compound, and hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between acetophenone and 3-buten-2-one. Draw the structure of the product of the enamine formed between acetophenone and pyrrolidine. Draw the structure of the Michael addition product. Draw the structure of the final product.

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