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JEE Advanced levelSingle correct optionDifficulty 3 of 3o2149

Benzene is treated with 1-chloro-2-methylpropane () and anhydrous . The major product is

  1. Asec-butylbenzene
  2. Btert-butylbenzene
  3. Cisobutylbenzene (2-methylpropylbenzene)
  4. Dn-butylbenzene

Answer: B

The primary isobutyl species rearranges by a 1,2-hydride shift to the tertiary tert-butyl cation. The tertiary cation is the most stable and is the species that alkylates benzene, so tert-butylbenzene is the major product. Isobutylbenzene could only be made reliably by acylation then reduction.
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