HOFMANN REARRANGEMENT Meaning and
Definition
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The Hofmann rearrangement refers to a chemical reaction that involves the conversion of primary amides into primary amines by undergoing a series of steps. It is named after the German chemist August Wilhelm von Hofmann, who first described the reaction in the 19th century.
In the Hofmann rearrangement, the primary amide reacts with hypochlorite ion (ClO-) in the presence of excess sodium hydroxide (NaOH). This results in the formation of an isocyanate intermediate, which further reacts with water to generate an amine and carbon dioxide. The overall reaction can be represented as follows:
RCONH2 + ClO- + NaOH → RNH2 + CO2 + NaCl + H2O
Here, R is an organic group attached to the nitrogen atom of the amide.
The Hofmann rearrangement has proven to be a useful method for synthesizing primary amines with one carbon atom less than the starting amide. It is particularly useful when there is a need to remove a carbonyl group from the nitrogen atom, as the reaction provides a means for selective conversion while leaving other functional groups intact.
The amine products obtained through the Hofmann rearrangement find various applications in organic synthesis, medicinal chemistry, and the production of pharmaceuticals and agrochemicals due to their high chemical reactivity and biological activity.
Etymology of HOFMANN REARRANGEMENT
The term "Hofmann rearrangement" is named after its discoverer, August Wilhelm von Hofmann. August Wilhelm von Hofmann was a German chemist who first described this chemical reaction in 1875. The reaction involves the conversion of a primary amide to an isocyanate by treatment with bromine and sodium hydroxide solution. This reaction is commonly known as the Hofmann rearrangement.
