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JEE Main levelNumerical answerDifficulty 2 of 3ap228

The diol shown is treated with dilute acid; ignore its stereochemistry. Water may be lost from either carbinol carbon, and either alkyl group on the neighbouring carbinol carbon may migrate. How many different carbonyl compounds (constitutional isomers; stereoisomers are not counted separately) can be formed? Answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 2

The diol is 3,4-dimethylhexane-3,4-diol. Both carbinol carbons carry one methyl and one ethyl group, so the cation may form at either carbon and the two sides are equivalent. Methyl migration gives the ketone and ethyl migration gives . These are two distinct compounds, so the answer is 2.
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