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Compounds Containing Nitrogen question

2011 · Shift 2 · Q11
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Compounds Containing Nitrogen question

2011 · Shift 2 · Q11

JEE AdvancedChemistryCompounds Containing NitrogenMCQ+3 / −1
Amongst the compounds given, the one that would from a brilliant coloured dye on treatment with NaNO2NaNO_2NaNO2​ in dil. HClHClHCl followed by addition to an alkaline solution of β\betaβ-naphthlol is
  1. A
    IIT-JEE 2011 Paper 2 Offline Chemistry - Compounds Containing Nitrogen Question 15 English Option 1
  2. B
    IIT-JEE 2011 Paper 2 Offline Chemistry - Compounds Containing Nitrogen Question 15 English Option 2
  3. C
    IIT-JEE 2011 Paper 2 Offline Chemistry - Compounds Containing Nitrogen Question 15 English Option 3
  4. D
    IIT-JEE 2011 Paper 2 Offline Chemistry - Compounds Containing Nitrogen Question 15 English Option 4
View written solutionFree

Correct answer: C

  1. What reaction is being tested?

    Treatment with NaNO2NaNO_2NaNO2​ and dilute HClHClHCl generates nitrous acid, which converts a primary aromatic amine into a diazonium salt at low temperature:

    ArNH2→dil. HClNaNO2ArN2+Cl−ArNH_2 \xrightarrow[\text{dil. }HCl]{NaNO_2} ArN_2^+Cl^-ArNH2​NaNO2​dil. HCl​ArN2+​Cl−

    This diazonium salt then couples with alkaline β\betaβ-naphthol to give a brightly coloured azo dye:

    ArN2+Cl−+β-naphthol→Ar−N=N−naphthol derivativeArN_2^+Cl^- + \beta\text{-naphthol} \rightarrow Ar-N=N-\text{naphthol derivative}ArN2+​Cl−+β-naphthol→Ar−N=N−naphthol derivative

  2. Which type of compound can do this?

    The compound must be a primary aromatic amine such as aniline or a substituted aniline.

    • Primary aromatic amine →\to→ gives stable diazonium salt →\to→ azo dye forms.
    • Primary aliphatic amine →\to→ diazonium salt unstable, decomposes.
    • Secondary/tertiary amines →\to→ do not give this azo-coupling test in the same way.
    • Amides/nitro compounds/etc. →\to→ do not directly diazotize to form the dye.
  3. Conclusion

    Therefore, among the given options, the correct compound must be the one corresponding to a primary aromatic amine. Since the stored correct answer is C, option C must be that compound.

  4. Final answer

    C\boxed{C}C​

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