Alkaline hydrolysis

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Alkaline hydrolysis, in organic chemistry, usually refers to types of nucleophilic substitution reactions in which the attacking nucleophile is a hydroxide ion.


In the alkaline hydrolysis of esters and amides the hydroxide ion nucleophile 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.[1]

Reacting isotopically labeled ethyl propionate with sodium hydroxide proves the proposed mechanism for nucleophilic acyl substitution.


Drain cleaners take advantage of this method to dissolve hair and fat in pipes.

See also[edit]


  1. ^ McMurry, John (1996). Organic Chemistry (4th ed.). Pacific Grove, CA: Brooks/Cole Publishing Company. pp. 820–821. ISBN 0534238327.