In the alkaline hydrolysis of esters and amides the hydroxide ion nucelophile attacks the carbonyl carbon in a nucleophilic acyl substitution reaction. This mechanism is supported by isotope labeling experiments. For example, when ethyl propionate with an oxygen-18 labeled ethoxy group is treated with sodium hydroxide (NaOH), the oxygen-18 is completely absent from the sodium propionate product and is found exclusively in the ethanol formed.
Drain cleaners take advantage of this method to dissolve hair and fat in pipes.
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