Chapter 22, Problem 58DSP

Interpretation Introduction

Interpretation:

The major product of the given reaction sequenceis to be determined.

Concept Introduction:

Reaction of an aldehyde or a ketone with a secondary amine gives an enamine.

If the aldehyde or ketone is unsymmetrical, then a mixture of two enamines is obtained.

In this mixture of enamines, the one with the less substituted double bond predominates.

Enamines are nucleophilic and react with electrophiles forming a new carbon-carbon bond. Further, hydrolysis produces a derivative of the original aldehyde or ketone such that the substituent is attached to the alpha position.

Primary alkyl halides and benzylic halides react with enamines to produce alpha substituted alkyl or benzyl derivatives of aldehydes or ketones.