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Reactions of Aryl Amines (Diazo Salts)

CaC 2 A B C D...

Question

${C a C}_{2} H y d r o l y s i s - ----- \to A R e d h o t - --- \to C u t u b e B {H N O}_{3} - H_{2} {S O}_{4} - -------- \to {50 - 60}^{0} C C F e + H C l - ---- \to D {N a N O}_{2} + H C l, 0^{0} C - ---------- \to E$

In the reaction sequence given above, $E$ is:

A

aniline

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B

benzene diazonium chloride

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C

phenyl osazone

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D

benzoyl chloride

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Solution

The correct option is C benzene diazonium chloride
Hydrolysis of calcium carbide yields ethyne.
$C a C_{2} + 2 H_{2} O \to C_{2} H_{2} + C a (O H)_{2}$

Now, in the presence of red hot copper tube, $3$ molecules of ethyne polymerize to give benzene.
$3 C_{2} H_{2}$ + red hot $C u$ tube $\to C_{6} H_{6}$ (benzene)

In the presence of $H N O_{3} - H_{2} S O_{4}$ , nitration of benzene occurs (electrophilic aromatic substitution) and nitrobenzene is formed.
$C_{6} H_{6} + H N O_{3} - H_{2} S O_{4} \to C_{6} H_{5} N O_{2}$ (nitrobenzene)

In the presence of $F e - H C l$ , nitrobenzene reduces to aniline.
$C_{6} H_{5} N O_{2} + F e - H C l \to C_{6} H_{5} N H_{2}$ (aniline)

Aniline on reaction with $N a N O_{2} - H C l$ gives benzene diazonium chloride.
$C_{6} H_{5} N H_{2} + N a N O_{2} - H C l \to C_{6} H_{5} N_{2}^{+} C l^{-}$

The complete reaction sequence is as follows:

${C a C}_{2} H y d r o l y s i s - ----- \to C_{2} H_{2} R e d h o t - --- \to C u t u b e C_{6} H_{6} {H N O}_{3} - H_{2} {S O}_{4} - -------- \to {50 - 60}^{0} C C_{6} H_{5} N O_{2} F e + H C l - ---- \to C_{6} H_{5} N H_{2}$

$N a N O_{2} + H C l, 0^{o} C - ---------- \to C_{6} H_{5} N_{2}^{+} C l^{-}$

Therefore, $E$ is benzene diazonium chloride.

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