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JEE Advanced levelNumerical answerDifficulty 3 of 3ap072

One mole of methyl 3,4-dihydroxybutanoate, , is treated with a large excess of in dry ether, followed by . Assume that each acidic consumes one mole of Grignard reagent (releasing ), that the ester is converted completely to a tertiary alcohol, and that no other reaction occurs. How many moles of are consumed per mole of the compound?

Numerical answer type, tolerance 0.5.

Answer: 4

Each of the two groups consumes one equivalent of and liberates methane, giving equivalents. An ester reacts with two equivalents of Grignard reagent (ketone intermediate, then tertiary alcohol), giving more. Total moles.
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