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Nucleophilic Substitution Reaction

An organic co...

Question

An organic compound ' $A$ ' having molecular formula $C_{2} H_{3} N$ on reduction gave another compound $B$ , upon treatment with nitrous acid ' $B$ ' gave ethyl alcohol. On warming with chloroform and alcoholic $K O H$ , it formed an offensive smelling ' $C$ '. The compound ' $C$ ' is:

A

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

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B

C H_{3} C H_{2} N \to = C

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C

C H_{3} C \equiv N

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D

C H_{3} C H_{2} \cdot O H

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Solution

The correct option is A $C H_{3} C H_{2} N \to = C$
(i) Proceed back with known compound $C_{2} H_{5} O H$
(ii) $1^{\circ}$ amine on reaction with $H N O_{2}$ gives $1^{\circ}$ alcohol
$C H_{3} - C \equiv N m e t h y l c y a n i d e (A) R e d u c t i o n - ----- \to C H_{3} C H_{2} N H_{2} \cdot H O N O - --- \to C H_{3} C H_{2} O H e t h a n o l C H_{3} C H_{2} N H_{2} (B) C H C l_{3}, K O H - ------- \to C H_{3} C H_{2} e t h y l i s o c y a n i d e (C) N = \to C e t h a n a m i n e (B)$

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