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In the following sequence of reactions, acetic acid is converted into product C: CH3COOH + PCl5 → A A —(C6H6 / anhyd. AlCl3)→ B B —(C2H5MgBr / dry ether)→ C What is the structure of product C?

1. CH3–C(OH)(C2H5)C6H5
2. CH3CH(OH)C2H5
3. CH3COC6H5
4. CH3CH(OH)C6H5

Correct answer: CH3–C(OH)(C2H5)C6H5

Solution

The correct option is right because the sequence of reactions indicates that acetic acid is first converted to an acyl chloride, which then undergoes Friedel-Crafts alkylation with benzene to form a product that contains both a benzene ring and an ethyl group attached to a central carbon, resulting in the structure CH3–C(OH)(C2H5)C6H5.

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