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ChemistryMultiple correct+4 / -1Question 44 of 54

JEE Advanced 2026 · Paper 2, Chemistry question 8

In the following reaction sequence, P, Q, S and T are the major products.

The correct statement(s) about P, Q, S and T is(are)

Aniline with (1) (CH₃CO)₂O, pyridine; (2) conc. HNO₃, conc. H₂SO₄, 288 K gives P; P with (1) H₃O⁺, (2) NaNO₂/HCl, 273-278 K gives Q. Cumene with (1) O₂/H₃O⁺, (2) NaOH/CO₂, (3) H₃O⁺ gives S; S with Q in aqueous NaOH gives T.
Choose one or more options
Answer and worked solution

Official answer: B, D

First chain.

  • Aniline →(CHX3CO)X2O\xrightarrow{\ce{(CH3CO)2O}} acetanilide →nitration\xrightarrow{\text{nitration}} P == p-nitroacetanilide (a mononitro compound).
  • P →HX3OX+\xrightarrow{\ce{H3O+}} p-nitroaniline →NaNOX2/HCl, 273-278 K\xrightarrow{\ce{NaNO2/HCl},\ 273\text{-}278\text{ K}} Q == p-nitrobenzenediazonium chloride.

Second chain.

  • Cumene →OX2/HX3OX+\xrightarrow{\ce{O2}/\ce{H3O+}} phenol (+ acetone) →NaOH/COX2\xrightarrow{\ce{NaOH/CO2}} sodium salicylate (Kolbe) →HX3OX+\xrightarrow{\ce{H3O+}} S == salicylic acid.
  • S + Q in aqueous NaOH: azo coupling para to the phenolic OH gives T, 5-(4-nitrophenylazo)salicylic acid, an azo dye.

Statements.

  • (A) Ethanol reduces ArNX2X+\ce{ArN2+} to ArH (nitrobenzene); the ethanol becomes acetaldehyde, which is not aromatic. False.
  • (B) S has a free phenolic OH and gives the phthalein dye test. True.
  • (C) P has one nitro group. False.
  • (D) T is an azo compound: coloured. True.
Topics:Diazonium saltsAminesPhenolsDetection of functional groups
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