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COMEDK2025ChemistryHydrocarbonsActual

Consider the following reaction X [ (ii) Zn / H ₂ O ] (i) O ₃ 5-keto-2-methylhexanal The reactant ' X ' is:

Options

  1. A1,2-dimethylcyclopentene
  2. B1,3-dimethylcyclopentene
  3. C1,5-dimethylcyclopentene
  4. D1,4-dimethylcyclopentene

Correct answer

B. 1,3-dimethylcyclopentene

Step-by-step solution

Reductive ozonolysis cleaves the C=C bond and replaces it with two carbonyl groups. To find X, we perform reverse ozonolysis on the product. Product: 5-keto-2-methylhexanal O=CH-CH(CH₃)-CH₂-CH₂-C(=O)-CH₃ The two carbonyl carbons are C1 (aldehyde) and C5 (ketone). Joining C1 and C5 forms a 5-membered ring with a C=C between them. Substituents on the ring: C5 carries a CH₃ (C6), and C2 carries a CH₃ . Numbering to give lowest locants methyl groups at positions 1 and 3. X is 1,3-dimethylcyclopentene.

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