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Pubblicato in Henry Rzepa's Blog

Nucleophilic addition of cyanide to a ketone or aldehyde is a standard reaction for introductory organic chemistry. But is all as it seems? The reaction is often represented as below, and this seems simple enough. Cyanohydrin formation. But attention to detail suggests that, HCN being a weak acid, there will be only a very small concentration of cyanide anion in the presence of HCl.