Cyanohydrin Formation: Extending Carbonyls with CN−

Learn cyanohydrin formation: CN− nucleophilic addition to aldehydes/ketones, protonation, and equilibrium control. Includes common traps and practice questions.

  • Nucleophile: CN−
  • Electrophile: Aldehyde/ketone
  • Outcome: C–C bond formed; nitrile + alcohol on same carbon
  • Key feature: Equilibrium; favored for aldehydes and more electrophilic carbonyls
  • Typical conditions: HCN with catalytic base, or CN− source with controlled protonation
  • Exam type: Predict the major product
  • Exam type: Choose conditions
  • Exam type: Failure modes / distractors

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