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Reimer Tiemann Reaction

Which of the ...

Question

Which of the following would undergo Hoffmann bromide reaction to form primary amine?

A

R C O N H C H_{3}

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B

R C O N (C H_{3})_{2}

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C

R C O N H_{2}

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D

R C O N H O H

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Solution

The correct option is D $R C O N H_{2}$
In Hoffmann bromamide reaction, primary amide reacts with bromine and sodium hydroxide to form isocyanate, which is hydrolysed to give primary amine (with one carbon less) along with decarboxylation.
$R C O N H_{2} + B r_{2} + N a O H \to R - N = C = O H_{2} O \to - C O_{2} R N H_{2}$

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[CBSE PMT 1989]

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