20. Carboxylic Acid Derivatives:NAS
Acid-Catalyzed Ester Hydrolysis
11PRACTICE PROBLEM
The acidic and basic hydrolyses of a nitrile differ slightly. In acidic hydrolysis, the cyano group's nitrogen is protonated first to increase its electrophilicity, allowing water, a weak nucleophile, to attack. Deprotonation of oxygen follows, forming an enol tautomer of an amide, which is then subjected to proton transfer (tautomerism) to produce the amide product. Draw the mechanism of the acid-catalyzed hydrolysis of cyclohexanecarbonitrile to cyclohexanecarboxamide.
The acidic and basic hydrolyses of a nitrile differ slightly. In acidic hydrolysis, the cyano group's nitrogen is protonated first to increase its electrophilicity, allowing water, a weak nucleophile, to attack. Deprotonation of oxygen follows, forming an enol tautomer of an amide, which is then subjected to proton transfer (tautomerism) to produce the amide product. Draw the mechanism of the acid-catalyzed hydrolysis of cyclohexanecarbonitrile to cyclohexanecarboxamide.