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1. Propose a mechanism for the following transformation: R COOH (1) H₂C-O, (C₂H₂)₂NH (2) H₂O, acetate buffer R CH₂

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

Chapter16: Aldehydes And Ketones

Section: Chapter Questions

Problem 16.58P: Propose a mechanism for this isomerization.

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Concept explainers

Reactions at the Alpha Carbon Atom

The position next to the ketone or aldehyde functional group is termed as alpha position and the reaction which occurs at alpha position is called alpha substitution reaction. In an alpha substitution reaction, the alpha proton atom is substituted by an electrophile by the formation of an enol intermediate or enolate ion intermediate. Most of the carbonyl compounds go through an alpha substitution reaction.

Question

1. Propose a mechanism for the following transformation:
R
COOH
(1) H₂C-O, (C₂H₂)₂NH
(2) H₂O, acetate buffer
R
CH₂

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