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JEE Main 2018 · Chemistry · Hydrocarbons · hard

Benzene is treated with (CH3)2CHCH2Cl and anhydrous AlCl3, and the major product is then heated with hot alkaline KMnO4 followed by acidification.…

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Benzene is treated with (CH3)2CHCH2Cl\mathrm{(CH_3)_2CHCH_2Cl} and anhydrous AlCl3\mathrm{AlCl_3}, and the major product is then heated with hot alkaline KMnO4\mathrm{KMnO_4} followed by acidification. The final major organic product is
  1. A. benzoic acid
  2. B. tert-butylbenzene
  3. C. isobutylbenzene
  4. D. phthalic acid
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Answer: (B) tert-butylbenzene

The primary carbocation from isobutyl chloride undergoes a 1,2-hydride shift to the more stable tertiary carbocation (CH3)3C+\mathrm{(CH_3)_3C^+}, so Friedel-Crafts gives tert-butylbenzene, not isobutylbenzene. Side-chain oxidation by KMnO4\mathrm{KMnO_4} requires at least one benzylic hydrogen; the benzylic carbon of the tert-butyl group has none, so the side chain survives and the ring is not attacked. The final product is unchanged tert-butylbenzene.
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