JEE MainChemistryAldehydes and Ketones
Compound X (1,2-dimethylcyclohex-1-ene) is subjected to reductive ozonolysis ( O₃ / Zn, H₂O ) to give compound Y. Compound Y is then heated with dilute NaOH to form a major product Z. The IUPAC name of the major product Z is:
Options
- A3-methylcyclohept-2-en-1-one
- B1-(2-hydroxy-2-methylcyclopentyl)ethan-1-one
- C1-(2-methylcyclohex-1-en-1-yl)ethan-1-one
- D1-(2-methylcyclopent-1-en-1-yl)ethan-1-one
Correct answer
D. 1-(2-methylcyclopent-1-en-1-yl)ethan-1-one
Step-by-step solution
Reductive ozonolysis of 1,2-dimethylcyclohex-1-ene cleaves the double bond to form octane-2,7-dione ( CH₃-CO-CH₂-CH₂-CH₂-CH₂-CO-CH₃ ). Upon heating with dilute NaOH, octane-2,7-dione undergoes an intramolecular aldol condensation. The enolate can form at the terminal methyl (C1) or the internal methylene (C3). Attack by the C1 enolate on the C7 carbonyl would form a 7-membered ring, whereas attack by the C3 enolate on the C7 carbonyl forms a more stable 5-membered ring. Thus, the C3 enolate attacks C7, followed by