Structural formula of a cyanohydrin.
In cyanohydrin, a cyanohydrin is a functional group or class of matter with the general formula R2C (OH) CN, where R may be hydrogen, an alkyl or aryl. At industrial level, cyanohydrins are important in the production of carboxylic acids and amino acids.
Cyanohydrin can be formed by a reaction in which a ketone or aldehyde is treated with hydrogen cyanide. In view of the toxicity of this substance, sodium or potassium cyanide is usually the source of the cyanide ion. The necessary hydrogen ion is drawn to water: NaCN → Na + CN RRC = O + CN → RRC (O) CN RR'C (O) CN + H2O → RR'C (OH) CN
With Net Response: NaCN + RR'C = O → RR'C (OH) CN + NaOH
During the reaction, monitoring of pH is important. Too low pH will result in gaseous HCN, resulting in too high a pH, which results in a poorer reaction of the alcoholate with water to the final product. Examples
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