Nitrile
Nitriles contain the cyano group -C≡N. Learn how to identify, name, and understand nitrile hydrolysis.
Functional group
R–C≡N
How to name it with IUPAC
Include the carbon of -C≡N in the parent chain and use the -nitrile suffix. In CH₃C≡N, two carbons are counted including the nitrile carbon: ethanenitrile (acetonitrile).
Properties and applications
The nitrile group is polar and linear. Nitrogen has a lone pair, but nitriles are much less basic than amines. Acetonitrile is a common polar aprotic solvent.
Characteristic reaction
Acidic or basic hydrolysis can convert a nitrile first into an amide and then into a carboxylic acid. Reduction can give a primary amine.
Examples
Ethanenitrile (CH₃C≡N) · Propanenitrile (C₂H₅C≡N) · Benzonitrile (C₆H₅C≡N)
Do not confuse
Do not confuse nitrile R–C≡N with isonitrile R–N≡C: changing the connectivity changes the function and name.