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← JEE Advanced 2025 · Paper 2
ChemistryMultiple correct+4 / -2Question 39 of 48

JEE Advanced 2025 · Paper 2, Chemistry question 7

For the reaction sequence given below, the correct statement(s) is(are)

Tetralin (1,2,3,4-tetrahydronaphthalene) → [(i) KMnO4, H+, Δ; (ii) NH3, Δ, −2H2O] → X → [(i) strong heating; (ii) ethanolic KOH; (iii) R-Br] → Y → [NaOH] → aromatic compound + Z.
Choose one or more options
Answer and worked solution

Official answer: A, C

The sequence.

  1. Side-chain oxidation of tetralin gives phthalic acid.
  2. Heating with NHX3\ce{NH3} (losing 2 HX2O\ce{H2O}) gives phthalimide, X.
  3. Gabriel synthesis (KOH, then R-Br) gives N-alkylphthalimide, Y.
  4. NaOH hydrolysis gives sodium phthalate (the aromatic compound) and R−NHX2\ce{R-NH2}, Z.

Options.

  • (A) True. X and Y both contain C=O groups.
  • (B) False. Y has no NHX2\ce{NH2}, so no carbylamine (isocyanide) reaction.
  • (C) True. Z is a primary amine, so it reacts with Hinsberg's reagent.
  • (D) False. Z is an aliphatic amine, not aromatic.
Topics:AminesAromatic hydrocarbons and electrophilic substitutionAcid derivatives
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