Figure 9.17. Nucleophilic Acyl Substitution: Amide to Carboxylic Acid
Strong acid or base is needed to catalyze the hydrolysis of amides, which are normally quite stable.Hydrolysis can also occur if conditions are basic enough. The reaction is similar to an acid-catalyzed
reaction, except that the carbonyl oxygen is not protonated and the nucleophile is a hydroxide ion.
The product of this reaction would be the deprotonated carboxylate anion.
MCAT Concept Check 9.3:
Before you move on, assess your understanding of the material with these questions.In the formation of an amide from ammonia and an anhydride, what serves as the
nucleophile? The electrophile?Nucleophile:Electrophile:Define transesterification.