Esterification Experiment

Esters can be synthesized in a number of different ways. One common method is the acid catalyzed condensation of a carboxylic acid and an alcohol. The mechanism involves an initial protonation of the carboxylic acid to form a resonancestabilized cation. The addition of the alcohol to the cationic carbon and loss of one of the protons on the oxygen of the alcohol form a species called a geminal diol. Protonation of one of the hydroxyl groups in this diol, followed by loss of water, yields the ester product. To obtain significant yields of the product, the equilibrium must be shifted by either added excess of one of the starting materials or by removing water and/or the ester product.