Hydrolysis of Amides

Generally, amides can be hydrolyzed in either acidic or basic solution. The mechanisms are much like those of ester hydrolysis, but the reactions are very much slower, a property of great biological importance (which we will discuss later):

Amide hydrolysis can be an important route to amines. Hydrolysis under acidic conditions requires strong acids such as sulfuric or hydrochloric, and temperatures of about 100o

for several hours. The mechanism involves protonation of the amide on oxygen followed by attack of water on the carbonyl carbon. The tetrahedral intermediate formed dissociates ultimately to the carboxylic acid and the ammonium salt:

A brief summary of important amide reactions follows: