JEE Main 2022 (27 Jul, Shift 2) Chemistry Q76: Amines

Question

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 $131\pm2$. 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 :

Accepted Answer

Option 4: [figure: benzene ring bearing $\mathrm{\overset{+}{N}H_3Cl^-}$ (anilinium chloride)]

Answer

[figure: cyclohexa-1,3-diene-type ring (two double bonds drawn) bearing $\mathrm{\overset{+}{N}H_3Cl^-}$]

Answer

[figure: benzene ring with $\mathrm{NH_2}$ and Cl on adjacent carbons (2-chloroaniline)]

Answer

[figure: five-membered ring with two double bonds bearing $\mathrm{CH_2\overset{+}{N}H_3Cl^-}$]

Answer

[figure: benzene ring bearing $\mathrm{\overset{+}{N}H_3Cl^-}$ (anilinium chloride)]

JEE Main 27 July 2022, Shift 2, Chemistry Q76

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