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← JEE Advanced 2026 · Paper 1
ChemistryNumerical+4Question 43 of 48

JEE Advanced 2026 · Paper 1, Chemistry question 11

The sum of total number of carbonyl groups ( >C=O ) present in the major products X and Y in the following reactions is ____.

Top: 2,4-dimethyl-3-oxopentanedioic acid, HO₂C-CH(CH₃)-CO-CH(CH₃)-CO₂H, heated gives X.Bottom: 4-oxocyclopentane-1,2-dicarboxylic acid (a cyclopentanone with CO₂H groups on the two carbons farthest from the C=O) heated gives Y.
Answer and worked solution

Official answer: 4

X. HOX2C−CH(CHX3)−CO−CH(CHX3)−COX2H\ce{HO2C-CH(CH3)-CO-CH(CH3)-CO2H} is a β-keto diacid. On heating, both carboxyl groups are lost as COX2\ce{CO2}, giving pentan-3-one, CHX3CHX2COCHX2CHX3\ce{CH3CH2COCH2CH3}: 1 C=O.

Y. In 4-oxocyclopentane-1,2-dicarboxylic acid the carboxyl groups sit on the β-carbons of the ketone, not the α-carbons, so neither is a β-keto acid and neither decarboxylates. The adjacent cis carboxyl groups lose water to form a five-membered cyclic anhydride. Y keeps the ketone and adds two anhydride C=O groups: 3 C=O.

Total 1+3=41+3=4.