Nomenclature of Nitriles
They are named by ending the alkane name with -nitrile (ethanenitrile)
Structure and physical properties
They exhibit sp hybridization in both the carbon and the nitrogen. They are linear with a structure similar to alkynes.
Acidity and basicity
Nitriles are protonated on the nitrogen and have acidic hydrogens on the α-carbon with a pKa of 25.
Reduction of nitriles to amines and aldehydes
Lithium aluminum hydride transforms nitriles into amines, and DIBAL into aldehydes.
Hydrolysis of nitriles
They are hydrolyzed in acid- or base-catalyzed processes to carboxylic acids. This hydrolysis initially yields an amide which, in subsequent steps, is transformed into the acid.
Reaction with organometallics
Organometallics react with nitriles to give imine anions, which upon aqueous work-up lead to the neutral imine, which rapidly hydrolyzes to a ketone.
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