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Topic: Diazonium salts in synthesis· Organic Compounds Containing Nitrogen

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_12H_10N_2O. The structure of compoun…

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

4 substituted benzene options

1. nitrobenzene (\(C_6H_5NO_2\))

2. benzonitrile (\(C_6H_5CN\))

3. benzamide (\(C_6H_5CONH_2\))

4. aniline (\(C_6H_5NH_2\))

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Answer: 1. nitrobenzene (\(C_6H_5NO_2\))

Key idea: nitro compound \(\rightarrow\) amine \(\rightarrow\) diazonium salt \(\rightarrow\) azo dye.

  1. \(C_6H_5NO_2\xrightarrow{Sn/HCl}C_6H_5NH_2\)
  2. \(C_6H_5NH_2\xrightarrow{HNO_2}C_6H_5N_2^+Cl^-\) (unstable, B)
  3. With phenol: \(p\)-hydroxyazobenzene \(C_6H_5N=N-C_6H_4OH\), formula \(C_{12}H_{10}N_2O\).

Aniline (option 4) would not need Sn/HCl, so A is nitrobenzene.

Doubtly AI · 30 Oct 2026 AI-generated · not yet verified Report
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