Question:

Identify products A and B.

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Cold dilute KMnO4 causes syn-hydroxylation of the alkene to a vicinal diol; CrO3 then oxidises only the secondary alcohol (the tertiary one cannot be oxidised) to a ketone.
Updated On: Nov 4, 2026
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The Correct Option is C

Solution and Explanation

The substrate is 1-methylcyclopentene.
Step 1: Dil. KMnO4 at 273 K adds two OH groups across the C=C (syn-hydroxylation), giving A = 1-methylcyclopentane-1,2-diol (one tertiary OH on C-1 and one secondary OH on C-2).
Step 2: CrO3 oxidises the secondary alcohol to a ketone, while the tertiary alcohol is untouched, giving B = 2-hydroxy-2-methylcyclopentan-1-one.
This matches option (3). Option (2) would need ring cleavage (hot conc. KMnO4/ozonolysis), and option (4) needs dehydration, which does not happen here.
Answer: (3) A = 1-methylcyclopentane-1,2-diol, B = 2-hydroxy-2-methylcyclopentanone
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