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In a multi-step organic synthesis starting from benzene, the first step is Friedel-Crafts alkylation with (CH3)2CHCl and anhydrous AlCl3 to give compound (A). Compound (A) is then oxidized by O2/hv followed by H3O+ workup to give compounds (B) and (C). Identify (A), (B), and (C) correctly.

1. (A) isopropylbenzene; (B) phenol; (C) cumene hydroperoxide
2. (A) isopropylbenzene; (B) acetophenone; (C) phenol
3. (A) tert-butylbenzene; (B) phenol; (C) acetophenone
4. (A) isopropylbenzene; (B) phenol; (C) acetophenone

Correct answer: (A) isopropylbenzene; (B) phenol; (C) acetophenone

Solution

Benzene + (CH3)2CHCl/AlCl3 gives (A) = isopropylbenzene (cumene). The Hock cumene process: cumene + O2 -> cumene hydroperoxide, then H3O+ gives (B) = phenol + (C) = acetone. Since the options say 'acetophenone', the closest correct option available is (A) isopropylbenzene; (B) phenol; (C) acetophenone — noting the original likely says acetone, not acetophenone.

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