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The Hofmann
Rearrangement
M.Nawaz Shah
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.
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.
Hofmann degradation
Br2
H2O
Amide
,
Simultaneous
+
+
+
Mechanism
+ +𝐶𝑂2
Mechanism
Support for the mechanism
• Intermediates have been isolated.
(N-haloamide ,Isocyanate etc.)
These intermediates Yield the product of Hofmann
degradation.
Intramolecular or intermolecular?
D
D
D
Stereochemistry

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Hofmann rearrangement