Answered: The Stork reaction is a condensation…

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

Chapter19: Enolate Anions And Enamines

Section: Chapter Questions

Problem 19.57P

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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.

The Stork reaction is a condensation
reaction between an enamine donor and
an o.,ß-unsaturated carbonyl acceptor
The overall reaction consists of a three-
step sequence of
1. formation of an enamine from a
ketone,
2. Michael addition to an o,B
unsaturated carbonyl compound,
and
3. hydrolysis of the enamine in
dilute acid to regenerate the
ketone.
Consider the Stork reaction between
acetophenone and 3-buten-2-one.

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

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