RCHOHCN

RCHOHCN is a shorthand for cyanohydrin, a class of organic compounds formed when hydrogen cyanide (HCN) adds to aldehydes or ketones. For aldehydes, the reaction is R-CHO + HCN → R-CH(OH)CN. The product is commonly written as RCH(OH)CN, with R representing an alkyl or aryl group.

Synthesis and structure: Cyanohydrins are typically prepared by adding HCN to aldehydes or ketones in the presence of a base or catalyst at low temperature to minimize side reactions. The product bears both a hydroxyl and a nitrile group on adjacent carbons, giving a versatile functionalized building block.

Properties and reactivity: Cyanohydrins are polar and often sensitive to acid or base. The CN and OH groups enable various transformations, including hydrolysis of the CN group to yield alpha-hydroxy acids or further derivatization to give diverse products.

Safety: HCN is highly toxic, and cyanohydrins can release HCN under acidic or strongly basic conditions. Reactions are conducted with appropriate ventilation, protective equipment, and waste handling.

Applications: Cyanohydrins serve as versatile intermediates in organic synthesis, enabling construction of complex molecules, including pharmaceutical and natural product derivatives, by introducing both hydroxyl and nitrile functionalities.

See also: cyanohydrin, aldehydes, hydrogen cyanide, nucleophilic addition.