Hofmann Reaction or Hofmann Rearrangement

hoffmann

source : slide share.net

Hofmann Reaction or Hofmann Rearrangement

The conversion of an amide to an amine with one carbon atom less than amide , by the reaction of Bromine & alkali  ( NaOH or  KOH ) is known as Hofmann reaction.

RCONH2 +Br2 +4KOH —–>RNH2 +2KBr +K2CO3 +2H2O

Mechanism:

hoffmann1

 

hoffmann 34

hoffmann56

Applications:

1)Aliphatic and aromatic amines are formed from amides (upto 7 carbon atoms)

ex1hoffmann

Example:    R may be -CH3  , -CH2-CH3 ,-CH2-CH2-CH3 , -CH2-(CH2)2-CH3 , -CH2-(CH2)3-CH3 ,  -CH2-(-CH2)4-CH3

 

 

EX3hauffammnn

2)  Preparation of Aldehydes:

Amides of , β-unsaturated acid and -hydroxy acid are converted to aldehyde by hofmann reaction.

preparationofaldehyde