Given that reaction of pyrrolidine enamine of cyclohexanone with but-2-ene-3-one followed by hydrolysis and base treatment yields the product shown. Each step with its mechanism is to be given. Concept introduction: The steps involved in the reaction are i) Michael addition of enamine to cyclohexanone ii) A proton transfer iii) Hydrolysis to remove the amine iv) Abstraction of a proton from the diketone v) internal aldol reaction to form the second ring vi) Protonation and dehydration. To give: The mechanism of each step involved in reacting pyrrolidine enamine of cyclohexanone with but-2-ene-3-one followed by hydrolysis and base treatment to produce the product shown.

Question

Acetophenone and formaldehyde undergo a mixed aldol addition. Which compound will react as CH - acidic and carbonyl component respectively, and why? Show the structures of the favoured aldol addition and aldol condensation products.

Answer 1

Question

Chapter 23.SE, Problem 64AP

Interpretation Introduction

Interpretation:

Given that reaction of pyrrolidine enamine of cyclohexanone with but-2-ene-3-one followed by hydrolysis and base treatment yields the product shown. Each step with its mechanism is to be given.

Concept introduction:

The steps involved in the reaction are i) Michael addition of enamine to cyclohexanone ii) A proton transfer iii) Hydrolysis to remove the amine iv) Abstraction of a proton from the diketone v) internal aldol reaction to form the second ring vi) Protonation and dehydration.

To give:

The mechanism of each step involved in reacting pyrrolidine enamine of cyclohexanone with but-2-ene-3-one followed by hydrolysis and base treatment to produce the product shown.

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Acetophenone and formaldehyde undergo a mixed aldol addition. Which compound will react as CH - acidic and carbonyl component respectively, and why? Show the structures of the favoured aldol addition and aldol condensation products.

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 cyclohexanone and propenal Draw the structure of the product of the enamine formed between cyclohexanone and dimethylamine. - Michael addition to an α,β-unsaturated carbonyl compound, and - hydrolysis of the enamine in dilute acid to regenerate the ketone.

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.