Compound A (1-methylcyclopentene) is subjected to reductive ozonolysis to give an intermediate B. Compound B is then treated with dilute aqueous NaOH and heated to yield a major cyclic product C. The IUPAC name of compound C is:

Step-by-step solution

Reductive ozonolysis of 1-methylcyclopentene cleaves the C = C double bond to form 5-oxohexanal, a 1,6-dicarbonyl compound. The structure of 5-oxohexanal is CH ₃- CO - CH ₂- CH ₂- CH ₂- CHO . In the presence of dilute NaOH, an intramolecular aldol condensation occurs. The aldehyde carbonyl carbon is more electrophilic than the ketone carbonyl carbon, so it acts as the electrophile. The enolate can form at the -carbons of the ketone (C4 or C6). Attack by the C4 enolate on the aldehyde (C1) would form a highly strain