Sandmeyer Reaction: Diazonium → Aryl Halides/CN (Copper-Mediated Substitution)

Master the Sandmeyer reaction: replacing diazonium with Cl, Br, or CN using Cu(I) salts. Mechanistic outline, scope, and exam pitfalls.

  • Reaction: Ar–N2+ → Ar–X (X=Cl, Br, CN)
  • What it does: Installs halides or nitrile on aromatic ring
  • Typical reagents: CuCl, CuBr, CuCN
  • Key intermediate: Radical/copper pathway (often taught as single-electron steps)
  • Driving force: Loss of N2 gas
  • Exam type: Synthesis planning
  • Exam type: Predict product

Related Resources

All 194 Mechanisms — Aromatic & Organometallic (Advanced Orgo II) Mechanism Flashcards AI Reaction Predictor Ask the AI Tutor