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What (who) is cyanohydrin - definition
![[[Amygdalin]] is one of several naturally occurring cyanogenic glycosides.](https://commons.wikimedia.org/wiki/Special:FilePath/Amygdalin structure.svg?width=200 "[[Amygdalin]] is one of several naturally occurring cyanogenic glycosides.")
Wikipedia
In organic chemistry, a cyanohydrin or hydroxynitrile is a functional group found in organic compounds in which a cyano and a hydroxy group are attached to the same carbon atom. The general formula is R2C(OH)CN, where R is H, alkyl, or aryl. Cyanohydrins are industrially important precursors to carboxylic acids and some amino acids. Cyanohydrins can be formed by the cyanohydrin reaction, which involves treating a ketone or an aldehyde with hydrogen cyanide (HCN) in the presence of excess amounts of sodium cyanide (NaCN) as a catalyst:
- RR’C=O + HCN → RR’C(OH)CN
In this reaction, the nucleophilic CN− ion attacks the electrophilic carbonyl carbon in the ketone, followed by protonation by HCN, thereby regenerating the cyanide anion. Cyanohydrins are also prepared by displacement of sulfite by cyanide salts:
Cyanohydrins are intermediates in the Strecker amino acid synthesis. In aqueous acid, they are hydrolyzed to the α-hydroxy acid.
