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Reaction with Hydrogen Cyanide

Aldehydes and Ketones react with HCN to give hydroxynitriles. HCN is not used as it is an extremely poisonous gas. Instead KCN or sodium cyanide is acidified with a little sulfuric acid. The solution contains free cyanide ions and some hydrogen cyanide (HCN) from the reaction between the KCN and acid.The reaction is a nucleophilic addition. The CN- ion acts as the nucleophile and attacks the electron-deficient, slightly-positive carbon atom. A dative covalent bond is formed between the CN- and the carbon atom of the carbonyl group. The reaction is completed by the addition of a hydrogen atom from the acid, water or HCN molecule.

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Specification: OCR Chemistry A (H432), A-level, 6.1.2 Carbonyl compounds. Topic: Carbonyl Compounds.

Key terms in this lesson

nucleophilic addition
A reaction mechanism in which a nucleophile donates a lone pair of electrons to the electron-deficient carbon atom of a pi bond, without any group being displaced.
nucleophile
An atom or group of atoms that can donate a pair of electrons to form a new covalent bond.

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