Advanced Topic 821 of 1102 Organic Chemistry
Nitriles
Compounds with CN group, hydrolyzed to acids or reduced to amines.
In-depth explanation of Nitriles
Nitriles contain the cyano group, C triple bond N, bonded to an alkyl or aryl group. They are usually prepared by SN2 reaction of cyanide ion with a haloalkane, which adds one carbon to the chain. Hydrolysis with acid or base converts nitriles into carboxylic acids, while reduction with lithium aluminium hydride or catalytic hydrogenation gives primary amines. Because cyanide ion is a very toxic species, nitrile chemistry must be carried out with care.
Going deeper: Nitriles
Key ideas: R-CN has a linear sp carbon and is made by SN2 of cyanide with a haloalkane (adds one carbon), dehydration of amides, or the diazonium Sandmeyer reaction. Hydrolysis with acid or base gives a carboxylic acid via the amide; LiAlH4 or H2 and Ni gives a primary amine; DIBAL gives an aldehyde; Grignard gives a ketone. Cyanide is toxic, so use hood protocols.
Common mistakes and connections: Students use aryl halides with cyanide in SN2, which fails; use diazonium salts instead. Another error is expecting reduction with NaBH4. Links to chain extension, Grignard additions, polyacrylonitrile and the carbylamine reaction, which gives isocyanides rather than nitriles.
Visualization of Nitriles
In IR the sharp C triple bond N stretch appears near 2250 cm-1, a clear signal for a nitrile group. The interactive lesson shows this as a live animation or chart.
Worked example and use case
Bromoethane reacts with cyanide to give propanenitrile, which hydrolyses to propanoic acid, CH3CH2Br giving CH3CH2CN giving CH3CH2COOH.
Frequently asked questions about Nitriles
What is Nitriles?
Compounds with CN group, hydrolyzed to acids or reduced to amines.
Is Nitriles a beginner, intermediate or advanced topic?
Nitriles is a advanced topic in Organic Chemistry. It builds on beginner and intermediate topics, so review those first if needed.
What should I learn before Nitriles?
Study these earlier topics in Organic Chemistry first: Diazonium Salts, Hofmann Degradation, Nitro Compounds.
What comes after Nitriles?
The next topics in Organic Chemistry are Thiols and Carbohydrate Structure.
Can I practise Nitriles with quizzes?
Yes. The interactive lesson includes a self-check question on Nitriles, and the Organic Chemistry quiz draws on every topic in this area.
Where Nitriles fits in Organic Chemistry
Nitriles is topic 93 of 148 in Organic Chemistry.