In this course I am offering you details of Hofmann Bromamide reaction which is also called as Hofmann degradation Reaction. In this course I have taken everything related to this including 21 concept building question which gives all types of permutation and combination related to topic. Here I have given
1. General Concept of Hofmann Bromamide reaction
3. Factors affecting its reactivity
4. Stereochemistry involved in it
5. Intramolecular nature of reaction
6. Twenty one best Questions which explains everything about it.
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In this course I am offering you details of Hofmann Bromamide reaction. In this course I have taken everything related to this including 21 concept building question which gives all types of permutation and combination related to topic.
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When a primary amide is treated with bromine in an aqueous or ethanolic solution of sodium hydroxide, degradation of amide takes place leading to the formation of primary amine. This reaction involving degradation of amide and is popularly known as Hoffmann bromamide degradation reaction.
The reaction of bromine with sodium hydroxide forms sodium hypobromite which transforms the primary amide into an intermediate isocyanate. The formation of an intermediate nitrene is not possible because it implies also the formation of a hydroxamic acid as a byproduct, which has never been observed. The intermediate isocyanate is hydrolyzed to a primary amine, giving off carbon dioxide.
Here following steps occur in reaction
Base abstracts an acidic N-H proton, yielding an anion.
The anion reacts with bromine in an α-substitution reaction to give an N-bromoamide.
Base abstraction of the remaining amide proton gives a bromoamide anion.
The bromoamide anion rearranges as the R group attached to the carbonyl carbon migrates to nitrogen at the same time the bromide ion leaves, giving an isocyanate.
The isocyanate adds water in a nucleophilic addition step to yield a carbamic acid (aka urethane).
The carbamic acid spontaneously loses carbon dioxide yielding the primary amine as product.