SolutionsHydrolysis of Carboxylic Acid Derivatives
1. Hydrolysis products
Give the products of: a) benzoyl chloride with water; b) acetic anhydride with water; c) ethyl acetate with aqueous NaOH; d) N,N-dimethylbenzamide with HO− and then H3O+.
- Benzoic acid and HCl.
- Two molecules of acetic acid.
- Sodium acetate and ethanol (acetic acid is released on acidification).
- Benzoic acid and the dimethylammonium salt, (CH3)2NH2+.
2. A hydrolysis with no way back
Acid hydrolysis of an ester is an equilibrium, but saponification goes to completion. Why?
In basic medium the acid formed is immediately deprotonated to the carboxylate, which is not electrophilic and does not react with the alcohol: the last step is a practically irreversible acid-base reaction.