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NEETChemistryAldehydes and Ketones

An unknown alkene 'X' undergoes reductive ozonolysis to yield a single compound 'Y'. Compound 'Y' on heating with dilute NaOH undergoes intramolecular aldol condensation to give 1-acetyl-2-methylcyclopentene as the major product. Identify alkene 'X'.

Options

  1. A2,3-Dimethylcyclohexene
  2. B1,4-Dimethylcyclohexene
  3. C1-Ethylcyclohexene
  4. D1,2-Dimethylcyclohexene

Correct answer

D. 1,2-Dimethylcyclohexene

Step-by-step solution

The final product is 1-acetyl-2-methylcyclopentene. Performing a retro-aldol analysis involves cleaving the , -unsaturated double bond (the C ₁= C ₂ bond of the cyclopentene ring). The C ₁ carbon is to the carbonyl group of the acetyl substituent, so it receives two hydrogen atoms. The C ₂ carbon is to the carbonyl, so it receives an oxygen atom to become a carbonyl group. This cleavage yields octane-2,7-dione ( CH ₃- C (= O )- CH ₂- CH ₂- CH ₂- CH ₂- C (= O )- CH ₃ ) as compound 'Y'. Compound 'Y' is formed by the

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