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Curtius and Hofmann Rearrangements

A compound ' ...

Question

A compound ' $X$ ' on treatment with $B r_{2} / N a O H$ , provided $C_{3} H_{9} N$ , which gives positive carbylamine test. Compound ' $X$ ' is:-

C H_{3} C O C H_{2} N H C H

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C H_{3} C H_{2} C O C H_{2} N H_{2}

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C H_{3} C H_{2} C H_{2} C O N H_{2}

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

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Solution

The correct option is B $C H_{3} C H_{2} C H_{2} C O N H_{2}$
$[X] B r_{2} - --- \to N a O H C_{3} H_{9} N C H C l_{3} - --- \to K O H C H_{3} C H_{2} C H_{2} - N C$
Hoff mann's Carbylamine
Bromamide Reaction
degradation

Thus $[X]$ must be aride with one carbon more than is amine.

Thus, $[X]$ is $C H_{3} C H_{2} C H_{2} C O N H_{2}$

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