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Q.

Consider all the esters of molecular formula C7H14O2 , excluding stereoisomers. They are all treated with an excess of methyl magnesium iodide and then acidified to give alcohols. Each ester produces two different alcohols [excluding stereoisomers], both of which react with Br2/NaOH to give bromoform. The number of esters, satisfying all these criteria, is______.

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answer is 4.

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Detailed Solution

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The esters must be formate esters so that they can give propan-2-ol with excess MeMgI, and the alcohol part of ester must by a methyl secondary alcohol.
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Consider all the esters of molecular formula C7H14O2 , excluding stereoisomers. They are all treated with an excess of methyl magnesium iodide and then acidified to give alcohols. Each ester produces two different alcohols [excluding stereoisomers], both of which react with Br2/NaOH to give bromoform. The number of esters, satisfying all these criteria, is______.