Acid-catalysed ester hydrolysis and transesterification

المؤلف:  Jonathan Clayden , Nick Greeves , Stuart Warren

المصدر:  ORGANIC CHEMISTRY

الجزء والصفحة:  ص 209-210

2025-05-11

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By starting with an ester, an excess of water, and an acid catalyst we can persuade the reverse reaction to occur: formation of the carboxylic acid plus alcohol with consumption of water. Such a reaction is known as a hydrolysis reaction because water is used to break up the ester into carboxylic acid plus alcohol (lysis=breaking).

Acid-catalysed ester formation and hydrolysis are the exact reverse of one another: the only way we can control the reaction is by altering concentrations of reagents to drive the reaction the way we want it to go. The same principles can be used to convert an ester of one alcohol into an ester of another, a process known as transesterification. It is possible, for example, to force this equilibrium to the right by distilling methanol (which has a lower boiling point than the other components of the reaction) out of the mixture.

The mechanism for this transesterification simply consists of adding one alcohol (here BuOH) and eliminating the other (here MeOH), both processes being acid-catalysed. Notice how easy it is now to confirm that the reaction is catalytic in H⁺.