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Amines as Bases

CH 3 CH 2 Cl ...

Question

${C H}_{3} {C H}_{2} C l N a C N - --- \to X P t / H_{2} - --- \to Y A c e t i c - ----- \to a n h y d r i d e Z$
In the above sequence, $Z$ is:

A

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

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B

{C H}_{3} {C H}_{2} {C H}_{2} {N H}_{2}

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C

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

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D

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

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Solution

The correct option is A ${C H}_{3} {C H}_{2} {C H}_{2} {N H C O C H}_{3}$
$C H_{3} C H_{2} C l + N a C N \to C H_{3} C H_{2} C N$

So, $X$ is $C H_{3} C H_{2} C N$ and is formed by nucleophilic substitution reaction ( $S_{N} 2$ )

Now, $C H_{3} C H_{2} C N + H_{2} / P t \to C H_{3} C H_{2} C H_{2} N H_{2}$

So, $Y$ is $C H_{3} C H_{2} C H_{2} N H_{2}$ and is formed by reduction reaction. The cyanide group on reduction gives amino group.
$C H_{3} C H_{2} C H_{2} N H_{2} + C H_{3} C O O C O C H_{3} \to C H_{3} C H_{2} C H_{2} N H C O C H_{3}$

So, $Z$ is $C H_{3} C H_{2} C H_{2} N H C O C H_{3}$ and is formed by addition-elimination reaction.

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