91Ó°ÊÓ

Phenyl acetonitrile is also known as benzyl cyanide. It is used as a precursor in the synthesis of various organic compounds.

A reaction occurs at -CN functional group which forms aldehydes, ketones, or amides.

Nitriles hydrolyze with water in the presence of an acid or base to give carboxylic acids or carboxylate anion.

a. ${\mathrm{H}}_3{\mathrm{O}}^{+}$

Reaction with water and acid

Reaction with water and base

The addition of R from the organometallic reagent (RMgX or RLi) forms a new C–C bond. Protonation forms an imine, which is hydrolyzed to a ketone.

c${\mathrm{CH}}_3\mathrm{MgBr},{\mathrm{H}}_2\mathrm{O}$

Reaction with Grignard reagent

d .${\mathrm{CH}}_3{\mathrm{CH}}_2\mathrm{Li},{\mathrm{H}}_2\mathrm{O}$

Reaction with alkyl lithium

The addition of H from DIBAL-H forms the new C–H bond. The protonation forms an imine, which is hydrolyzed to an aldehyde.

e.$\mathrm{DIBAL}-\mathrm{H},{\mathrm{H}}_2\mathrm{O}$

Reaction with DIBAL-H

The addition of one equivalent of H from forms an intermediate with one new C–H bond. Nucleophilic attack of the second equivalent of H forms a dianion, which reacts with water to form two new N–H bonds, giving the 1° amine

f.${\mathrm{LiAlH}}_4,{\mathrm{H}}_2\mathrm{O}$

Reaction with ${\mathrm{LiAlH}}_4$