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