Nitrile
Nitrile is a type of organic compound that has a cyanide group (-C≡N) which is bonded to a carbon atom. Nitriles are found in many useful compounds, including synthetic rubber and pharmaceuticals.
Structure and bonding[edit | edit source]
The C≡N functional group in a nitrile is linear, with a 180° bond angle. The carbon atom in the C≡N bond is sp hybridized, and the nitrogen atom is sp hybridized. The carbon-nitrogen triple bond is very strong and has a bond length of 1.16 Å.
Nomenclature[edit | edit source]
The IUPAC nomenclature for nitriles designates them as derivatives of carboxylic acids by changing '-ic acid' to '-onitrile', or '-carboxylic acid' to '-carbonitrile'. For example, the nitrile of acetic acid is acetonitrile (CH3CN).
Preparation[edit | edit source]
Nitriles can be prepared by several methods, including the dehydration of amides, the reaction of amines with cyanogen chloride, and the reaction of alcohols with hydrogen cyanide.
Reactions[edit | edit source]
Nitriles undergo various reactions, including hydrolysis to carboxylic acids, reduction to primary amines, and reaction with Grignard reagents to ketones.
Uses[edit | edit source]
Nitriles are used in the production of synthetic rubbers, plastics, and pharmaceuticals. They are also used as solvents and in the synthesis of organic compounds.
See also[edit | edit source]
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