JEE Main Chemistry question

Suggest appropriate structures for the missing final compound (the number of carbon atoms remains the same throughout the reaction): a methylcyclopentene --dil. KMnO₄--> A --HIO₄--> B --OH⁻--> ?

(A)A ring-opened keto-aldehyde product analogous to Q298's answer, cyclized back by intramolecular aldolCorrect
(B)An open, uncyclized diketone
(C)A simple diol
(D)A different open-chain product

Answer: (A)

Solution

Dilute cold KMnO₄ performs syn-dihydroxylation of the methylcyclopentene's double bond, giving a vicinal diol A. Periodic acid (HIO₄) then oxidatively cleaves this diol at the C–C bond between the two OH-bearing carbons, opening the ring to a keto-aldehyde chain B (identical in connectivity to the ozonolysis product

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Question ID VK-149344