Question

Compound A serves as a prodrug for the analgesic benzocaine. (A prodrug is a pharmacologically inactive compound that is converted in the body to an active drug, usually by a metabolic transformation.) The enzyme amidase catalyzes the hydrolysis of compound A into benzocaine. Write the structures of the possible products of A that might be formed by hydrolysis in aqueous HCl.

Answer 1

The hydrolysis in aqueous HCl of compound A can lead to the formation of a carboxylic acid and an alcohol.

Step-by-step explanation:

The picture shows the structures of compound A, benzoncaine and the possible products of the proposed reaction.

The acidic hydrolysis is the inverse of the esterification reaction. Therefore, the ester group of compund A will react to form the equivalent carboxylic acid and alcohol.

In order to form benzocaine, the hydrolysis happens in with the nitrile group.