One-Carbon Homologation via Cyanide (Carbonyl → Nitrile → Acid/Aldehyde): Mechanism + Exam Traps

A practical 'add one carbon' strategy: convert carbonyl to cyanohydrin/aminonitrile, then transform nitrile into carboxylic acid, amide, or amine.

  • Reaction: One-Carbon Homologation via Cyanide (Carbonyl → Nitrile → Acid/Aldehyde)
  • What it does: A practical 'add one carbon' strategy: convert carbonyl to cyanohydrin/aminonitrile, then transform nitrile into carboxylic acid, amide, or amine.
  • Typical reagents: NaCN (SN2), then optional hydrolysis/reduction downstream
  • Key intermediate: Varies / context-dependent
  • Driving force: Formation of more stable bonds / products
  • Exam type: Choose reagents
  • Exam type: Plan order of operations
  • Exam type: Chemoselectivity

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