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ChemistryInteger+4 / -1Question 36 of 60

JEE Advanced 2013 · Paper 1, Chemistry question 36

The total number of carboxylic acid groups in the product P is

A tricyclic compound: a cyclohexene ring fused to a cyclohexane-1,4-dione ring, which is fused to a succinic anhydride ring; it is treated with 1. H₃O⁺, Δ; 2. O₃; 3. H₂O₂ to give P.
Answer and worked solution

Official answer: 2

Step 1 (H₃O⁺, Δ). The anhydride hydrolyses to two COOH groups, each β to a ring ketone; these β-keto acids decarboxylate on heating, leaving a cyclohexanedione fused to the cyclohexene.

Steps 2-3 (O₃, H₂O₂). Oxidative ozonolysis cleaves the C=C into two COOH groups.

P has 2 carboxylic acid groups.

Answer: 2

Topics:Carboxylic acidsAcid derivativesAlkenes
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