Nitrile

Nitrile is a functional group in organic chemistry. Chemicals that have this group are also called nitriles. The nitrile group has a triple bond between a carbon atom and a nitrogen atom. This is written −C≡N. Inorganic nitriles are called cyanides.

Structure of the nitrile functional group. R is a placeholder for any organic compound.

It smells like a fruit, and can be a type of poison.^[source?]

The simplest nitrile is acetonitrile (CH₃CN, where the nitrile is connected to a methyl group. Acrylonitrile is a nitrile used to make plastics.

Reactions

With water

Nitriles react with water. This is a type of hydrolysis. Nitriles and water react to make amides, and the amide can react further to make carboxylic acids and ammonia:^[source?]

CH₃CN + H₂O → CH₃CONH₂

CH₃CONH₂ + H₂O → CH₃COOH + NH₃

With hydrogen

Hydrogen gas, H₂, is a reducing agent. Combined with a catalyst like Raney nickel, it reacts with nitriles to make amines.^[source?]