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Introduction
An amide is treated with bromine in an aqueous or ethanolic solution of sodium hydroxide in this reaction, resulting in amide breakdown and the generation of primary amine.
Hoffmann Bromamide Rearrangement (or) Hoffmann Bromamide Degradation is another name for the reaction.
Hofmann’s Reaction
An alkali will be used in the Hoffmann bromamide reaction as a strong base for the attack on the amide, which will lead to deprotonation and the production of an anion. This reaction is frequently used to convert a primary amide to a primary amine, which has one less carbon atom. This reaction will be carried out by heating the primary amide with a halogen, such as chlorine or bromine, a strong base, and a universal solvent, such as water.
Hoffmann bromamide degradion Reaction
The Hofmann rearrangement, also known as Hofmann degradation, is a chemical reaction in which primary amide is transformed to primary amine, with the resultant product containing one less carbon atom than the parent. The oxidation of nitrogen will be followed by the rearrangement of the carbonyl molecule and nitrogen to create an isocyanate intermediate in this reaction. And this reaction produces a diverse spectrum of compounds, including alkyl and aryl amines.
Hoffmann Bromamide Reaction Mechanism.
1st stage – The hydroxide ion from the strong base attacks the amide, causing it to deprotonate and subsequently create water with the amide anion.
2nd stage – The anion now attacks the diatomic bromine, causing an alpha substitution reaction that breaks the bromine-bromine bond, resulting in the formation of the N-Bromamide molecule and the Br- anion.
3rd stage — The base attacks the N-Bromamide that was generated in the previous step, causing it to deprotonate, resulting in the creation of water and the bromamide anion.
4th stage – the generated bromamide anion undergoes a rearrangement process in which the existence of an ethyl group or any other R- group that is bonded through the carbonyl carbon now creates bonds with the nitrogen. In addition, the generated bromide anion will depart the complex. An isocyanate will be produced as a result of this process.
5th stage – when the process of hydrolysis, i.e. water addition, occurs in isocyanate, it results in the synthesis of carbamic acid, and the pathway followed in this process is the nucleophilic addition reaction.
6th stage — The carbamic acid generated in the previous step now loses a carbon dioxide molecule and produces a negative charge with nitrogen, i.e. it is coupled with one hydrogen and the ethyl group. The needed primary amine will be generated when this molecule is protonated through water.
Uses Of Hoffman Bromide Reaction
1.It include the generation of primary aromatic and aliphatic amines.
2.It’s also employed in the manufacture of aniline molecules.
3.It’s also used to make anthranilic acid and phthalimide, among other things.
4.Through nicotinic acid, this process also produces 3-aminopyridine.
5.The symmetrical structure of the molecule, phenyl propanamide, will not be altered by the Hoffmann reaction.
6.The mechanism of the Hoffmann bromamide reaction will comprise an alkali that will operate as a strong base for the attack on the amide, leading to deprotonation and the production of an anion. This reaction is frequently used to convert a primary amide to a primary amine, which has one less carbon atom. This reaction will be carried out by heating the primary amide with a halogen, such as chlorine or bromine, a strong base, and a universal solvent, such as water.
Conclusion
We conclude that when bromine is added to an amide in an aqueous or ethanolic sodium hydroxide solution, the amide degrades, resulting in the creation of primary amine. Hoffmann bromamide degradation reaction is a reaction that involves the degradation of an amide.
