JEE Main 2022 · 27 Jul · Shift 2 · Chemistry Q76

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ChemistrySingle correct+4 / -1Question 76 of 90

An organic compound 'A' contains nitrogen and chlorine. It dissolves readily in water to give a solution that turns litmus red. Titration of compound 'A' with standard base indicates that the molecular weight of 'A' is 131 ± 2. When a sample of 'A' is treated with aq. NaOH, a liquid separates which contains N but not Cl. Treatment of the obtained liquid with nitrous acid followed by phenol gives orange precipitate. The compound 'A' is :

Cyclohexa-2,5-dienyl-

\mathrm{\overset{+}{N}H_3Cl^-}

2-Chloroaniline

Cyclopentadienyl-

\mathrm{CH_2\overset{+}{N}H_3Cl^-}

A cyclopentadiene ring bearing CH2NH3+ Cl−.

Anilinium chloride,

\mathrm{C_6H_5\overset{+}{N}H_3Cl^-}

Answer and worked solution

Official answer: D

Clues. An acidic, water-soluble salt with M ≈ 131 (anilinium chloride is 129.5). NaOH frees aniline (contains N, not Cl), and diazotisation then coupling with phenol gives an orange azo dye.

(D)

Topics:Amines Diazonium salts

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JEE Main 2022 · 27 Jul · Shift 2, Chemistry question 76