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An ester (A) with molecular formula, C9H10O2, was treated with excess of CH3MgBr and the complex so formed was treated with H2SO4 to give an olefin (B). Ozonolysis of (B) gave a ketone with molecular formula C8H8O which shows +ve iodoform test. The structure of (A) is

1. C6H5COOCH3
2. C6H5COOC2H5
3. H3COCH2COC6H5
4. p-H3CO-C6H4-COOCH3

Correct answer: C6H5COOCH3

Solution

The ester (A) reacts with CH3MgBr to form a tertiary alcohol, which upon acid treatment gives an olefin (B). Ozonolysis of (B) produces a ketone (C8H8O) that gives a positive iodoform test, indicating the presence of a methyl ketone group. The structure of (A) must be C6H5COOCH3.

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