Benzonitrile

Benzonitrile is an aromatic nitrile with formula C₆H₅CN: a benzene ring bonded directly to a cyano group.

Benzene: Benzene is a six-carbon aromatic hydrocarbon with formula C₆H₆ and a planar ring of delocalized electrons. Benzonitrile retains benzene’s ring, with one hydrogen replaced by a cyano group.
Electrophilic aromatic substitution: Electrophilic aromatic substitution replaces a hydrogen on an aromatic ring with an electrophile while restoring aromaticity. The cyano group deactivates benzonitrile’s ring and directs substitution mainly to the meta position.
Benzamide: Benzamide is the primary amide derived from benzoic acid, with formula C₆H₅CONH₂. Partial hydrolysis of benzonitrile can produce this amide.
Acetonitrile: Acetonitrile is a polar organic solvent with formula CH₃CN and a methyl group bonded to a cyano group. Unlike benzonitrile, it is an aliphatic nitrile without an aromatic ring.
Nitrile: A nitrile is an organic compound containing a carbon–nitrogen triple bond, typically written R–C≡N. Benzonitrile belongs to this class because its cyano carbon is bonded to phenyl.
Nucleophilic aromatic substitution: Nucleophilic aromatic substitution replaces a leaving group on an aromatic ring with a nucleophile. A cyano group can stabilize anionic intermediates when positioned to activate a ring leaving group.
Benzoic acid: Benzoic acid is an aromatic carboxylic acid with formula C₆H₅COOH. Complete hydrolysis of benzonitrile converts its nitrile group into this carboxylic acid.
Toluonitrile: Toluonitrile is a methyl-substituted benzonitrile, occurring as ortho, meta, and para isomers. Its additional ring methyl group distinguishes it from unsubstituted benzonitrile.
Cyano group: The cyano group is the functional group –C≡N, consisting of carbon triple-bonded to nitrogen. This is the substituent attached to benzonitrile’s benzene ring.
Nitrile hydrolysis: Nitrile hydrolysis converts a nitrile into a carboxylic acid, often through an amide intermediate. Hydrolysis of benzonitrile yields benzoic acid under suitable acidic or basic conditions.

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Lithium aluminium hydrideRelated: LiAlH₄ converts its nitrile group into benzylamine after workup.