JEE Main 2026 · 5 April · morning · Single correct · +4 / −1

"P" is a hydrocarbon of molecular formula:- C₈H₁₄. On ozonolysis, "P" forms "Q". "Q" on treatment with alkali under reflux condition produces "R", which on treatment with I₂/NaOH gives a yellow precipitate. Acidification of the solution gives "S". The structure of "S" is given below:-
The correct structure of "P" is

JEE Main PYQ figure
  1. (a)
    Option (a)
  2. (b)
    Option (b)
  3. (c)
    Option (c)
  4. (d)
    Option (d)
Answer and solution

Answer (d)

Solution

Chemistry ma’am · 4 steps

Work backwards: aldol builds the ring in S, so Q is a 1,6-diketone cut open from a cyclohexene.

  1. Undo the iodoform. The yellow precipitate is CHI₃, so R has a CH₃CO⁻ group, and I₂/NaOH turns it into -COOH. Put the CH₃ back on the COOH of S: R is 1-acetyl-2-methylcyclopentene, C₈H₁₂O.
  2. Undo the aldol. The ring C=C in R comes from aldol condensation, which loses one H₂O. Open that bond and add the water back: Q is octane-2,7-dione, CH₃CO(CH₂)₄COCH₃, C₈H₁₄O₂. Its two C=O groups are in a 1,6 relationship, and the enolate of the CH₂ next to one C=O attacks the other C=O to close a five-membered ring.

    CH₃CO(CH₂)₄COCH₃ →(OH⁻, Δ) 1-acetyl-2-methylcyclopentene →(I₂/NaOH, H₃O⁺) S + CHI₃

  3. Undo the ozonolysis. Both carbonyl groups sit in one chain, so they came from a single C=C inside a ring. Join the two carbonyl carbons with a double bond. This gives a six-membered ring with a methyl group on each alkene carbon: 1,2-dimethylcyclohexene, C₈H₁₄, which matches P.
  4. So. P is 1,2-dimethylcyclohexene, option (d).

The idea to keep. Ozonolysis of a ring alkene gives one open-chain dicarbonyl. A 1,6-dicarbonyl closes by aldol to a five-membered ring, and a 1,5-dicarbonyl closes to a six-membered ring.

Answer from the NTA final answer key. Solution by PrepWiser.

Study Aldehydes & Ketones

Asked about 130 times in JEE Main since 2020. This question is from 2026.