A given nitrogen-containing aromatic compound A reacts with Sn/HCl, followed by HNO₂ to give an unstable compound B. B, on…

A given nitrogen-containing aromatic compound A reacts with Sn/HCl, followed by $HNO_2$ to give an unstable compound B. B, on treatment with phenol, forms a beautiful coloured compound C with the molecular formula $C_{12}H_{10}N_2O$. The structure of compound A is:
A -
B -
C -
D -

Explanation

Reduction, diazotisation and coupling with phenol give an azo dye.

Detailed Solution


$C_6H_5NO_2$ (A) $\xrightarrow{Sn + HCl\ (reduction)}$ $C_6H_5NH_2$ (aniline) $\xrightarrow{HNO_2}$ $C_6H_5N_2^+Cl^-$ (B, benzene diazonium chloride)
B + phenol → p-hydroxyazobenzene, $C_6H_5-N=N-C_6H_4-OH$ (C, coloured dye)
So A is nitrobenzene.

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