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Curtius and Hofmann Rearrangements

How primary a...

Question

How primary amine is prepared by Hoffmann bromamide degradation reaction? Write equation.

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Solution

Amides on treatment with bromine in an aqueous solution of sodium hydroxide forms primary amine.
$R - O | | C - N H_{2} + B r_{2} + 4 N a O H \to R - N H_{2} + N a_{2} C O_{3} + 2 N a B r + 2 H_{2} O$ .
The product (amine) has one carbon atom less than starting material (amide).

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Curtius and Hofmann Rearrangements

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