FPGEE for National Association of Boards of Pharmacy (NABP) Practice Exam 2026 - Free NABP Practice Questions and Study Guide

Esters are the most at risk of hydrolysis due to their chemical structure and the nature of their functional group. In essence, esters contain a carbonyl group (C=O) and an ether-like bond (C-O-R), which makes them susceptible to nucleophilic attack, primarily by water. This results in a reaction known as hydrolysis, where the ester breaks down into an alcohol and a carboxylic acid.

The conditions that facilitate this hydrolysis can be either acidic or basic. In acidic conditions, water acts as a nucleophile, while in basic conditions, hydroxide ions can help drive the reaction. The process is fairly common in nature and synthetic chemistry, indicating that esters readily react with water, especially when heat is applied or in the presence of a catalyst.

In contrast, alkanes are saturated hydrocarbons that are relatively unreactive and lack functional groups that would make them susceptible to hydrolysis. Alcohols, while they contain a hydroxyl (-OH) group that can participate in reactions with water, do not undergo hydrolysis in the same manner as esters. Amines can also react with water, but they do not undergo hydrolysis in the same way as esters do. Instead,