Hofmann rearrangement

These slides present the introduction of Hofmann rearrangement, mechanism, intramolecular rearrangement, and stereochemistry.

1. The Hofmann Rearrangement M.Nawaz Shah

2. August Wilhelm von Hofmann Born in Germany (1818-1892) Law Chemistry German chemical society German dyes industry Royal college of chemistry in London University of Berlin Married four times He had 11 children.

3. Introduction Amides with no substituent on the nitrogen react with solutions of bromine or chlorine in sodium hydroxide to yield amines through a reaction known as the Hofmann rearrangement or Hofmann degradation.

4. Hofmann degradation Br 2 H 2 O Amide ,

5. Simultaneous

6. + + + Mechanism

7. + +   Mechanism

8. Support for the mechanism Intermediates have been isolated. (N-haloamide ,Isocyanate etc.) These intermediates Yield the product of Hofmann degradation.

9. Intramolecular or intermolecular? D D D

10. Stereochemistry