nitrile

An organic compound containing the nitrile group (–CN). Nitriles are also known as organic cyanides (see cyanide). They are named for the carboxylic acid to which they can be hydrolyzed. The simplest is acetonitrile (or methyl cyanide), CH₂CN. Nitriles are prepared by dehydration of amides or by reaction of sodium cyanide with alkyl halides or aryl sulfonates.

The aliphatic or alkyl nitriles are important in ascending the homologous series, since they enable an extra carbon atom to be introduced into the molecule. The alkyl nitriles are reduced by hydrogen to give primary amines, and react with Grignard reagents to yield ketones.

Nitriles are important precursors of amino acids. Industrially, nitriles are used in organic synthesis, notably for the manufacture of acrylic fabrics and synthetic rubber.

Related category

• ORGANIC CHEMISTRY

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