Ketones and aldehydes react with primary amines to give

QUESTION:

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.

\(\mathrm{CH}_{3} \mathrm{NH}_{2}\)

\(\mathrm{NHCH}_{3}\)

\(\mathrm{H}_{2} \mathrm{O}\)

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

\(\mathrm{H}_{2} \mathrm{O}\)

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

Equation transcription:

Text transcription:

{CH}{3}{NH}{2}

{NHCH}{3}

{H}{2}{O}