Which of the following compounds cannot be identified by carbylamine test?

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

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

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C_{6} H_{5} N H_{2}

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C_{6} H_{5} N H C_{6} H_{5}

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Solution

The correct option is D $C_{6} H_{5} N H C_{6} H_{5}$
$C_{6} H_{5} N H C_{6} H_{5}$ diphenylamine is a secondary amine and secondary and tertiary amines do not show carbylamine reaction.

Hoffman carbylamine test is given by only primary amines as the nitrogen in the amine group has one lone pair of electron and two hydrogen atoms, which form bonds with the carbene, formed from the chloroform, which in turn help in the formation of isocyanide.

$R - N H_{2} C H C l_{3}, K O H - ------- \to R - N C$

Option D is correct.

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C H_{3} N H_{2}

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[C H_{3} C H_{2} N H_{2} + {(C H_{3})}_{2} C H N H_{2}]

H C l

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