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Organic Chemistry Text Book (CHEM 3401 and 3402)

20.7.3b Nitrile Hydrolysis

Although they do not have a carbonyl group, nitriles are often treated as derivatives of carboxylic acids. Hydrolysis of nitriles to carboxylic acids was described earlier, and requires reaction conditions (catalysts and heat) similar to those needed to hydrolyze amides. This is not surprising, since addition of water to the carbon-nitrogen triple bond gives an imino intermediate which tautomerizes to an amide.


R–C≡N   +   H2O
acid or base