Beckmann Rearrangement: Oximes → Amides/Lactams (Anti Group Migrates!)

Master the Beckmann rearrangement: activating oximes, anti-migration rule, nitrilium intermediate, and hydrolysis to amides/lactams (e.g., caprolactam).

  • Reaction: Oxime → amide (or lactam)
  • What it does: Rearranges ketoximes to amides (ring expansion in cyclic cases)
  • Typical reagents: Acid (H2SO4) or sulfonyl chloride activators
  • Key intermediate: Nitrilium ion
  • Driving force: Formation of stable amide after hydrolysis
  • Exam type: Rearrangements
  • Exam type: Stereospecificity

Related Resources

All 194 Mechanisms — Rearrangements & Named Curiosities Mechanism Flashcards AI Reaction Predictor Ask the AI Tutor