Nitrile

A nitrile is an organic compound containing a carbon triple bonded to nitrogen.

Synthesis

• The Sandmeyer reaction employing cuprous cyanide can be used to form nitriles from diazonium compounds.
• Aryl nitriles may be formed from aryl halides in the Rosenmund-von Braun reaction.
• The reaction of cyanide with aldehydes or ketones forms a cyanohydrin (ά-hydroxynitrile).
• Amides may be dehydrated to nitriles with a variety of reagents

Reactivity

• Nitriles are reduced to amines by hydrogen and a nickel catalyst
• Nitriles are reduced to imines, then hydrolyzed to the aldehyde in the Stephens aldehyde synthesis.
• Beta-ketoesters are formed from alpha-bromoesters and nitriles in the Blaise reaction.
• Nitriles are hydrolysed to amides by acid