Ketones and aldehydes react with primary amines to give imines. They react with secondary amines to give enamines (vinyl amines).
(a) For review, propose a mechanism for the following formation of an imine.

(b) Now give a mechanism for a similar reaction that gives an enamine.

(c) Explain why the reaction with the secondary amine gives an enamine rather than an imine.

Transcribed Image Text:

NHCH + CH3NH2- +H2C an imine +H,O