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JEE Main Chemistry question

ChemistryAldehydes, Ketones and Carboxylic AcidsJEE Main

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 a positive iodoform test. The structure of A is

Answer: (D)

Solution

With excess CH₃MgBr, the ester A (C₉H₁₀O₂) forms a tertiary alcohol; acid-catalyzed dehydration gives the olefin B. Ozonolysis of B gives a C₈H₈O ketone that gives a positive iodoform test, meaning it is a methyl aryl ketone (p-methoxyacetophenone, C₈H₈O₂... checking the formula: actually the ketone must be consistent

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Question ID VK-149323