Organic Chemistry MCAT Practice Exam

Hydrolysis of cyanohydrins typically leads to the formation of carboxylic acids. A cyanohydrin is a compound that contains a cyano group (–C≡N) and a hydroxyl group (–OH) attached to the same carbon atom. When subjected to hydrolysis, particularly in the presence of water and an acid or base catalyst, the cyano group undergoes conversion to a carboxylic acid. The process involves the addition of water across the cyano group, which converts the nitrile functionality into a carboxylic acid. This reaction is straightforward and occurs as the nucleophilic attack of water on the carbon of the cyano group leads to the formation of an intermediate, which ultimately rearranges to yield the carboxylic acid. This conversion is significant in organic synthesis, as producing carboxylic acids from cyanohydrins expands the repertoire of functional groups available for further reactions and modifications in synthetic pathways. Thus, the consequence of hydrolyzing cyanohydrins being the formation of carboxylic acids is rooted in the fundamental reaction mechanisms involving nucleophilic attack on the cyano group.