Hofmann Rearrangement: Amides → Amines (One Carbon Shorter)

Learn Hofmann rearrangement: N-bromination, rearrangement to isocyanate, hydrolysis to amine with one fewer carbon. Key rules and pitfalls.

• Reaction: RCONH2 → RNH2 (one carbon shorter)
• What it does: Deletes the carbonyl carbon from amides
• Typical reagents: Br2, NaOH (or other halogen/base combos)
• Key intermediate: Isocyanate
• Driving force: Loss of CO2 during hydrolysis; formation of stable products
• Exam type: Rearrangements
• Exam type: Carbon counting