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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3hc220

Which of the following, on side-chain monochlorination with /light (no ring substitution), give only one constitutional isomer of the monochloro product?

  1. AToluene
  2. BEthylbenzene
  3. Cp-Xylene (1,4-dimethylbenzene)
  4. Dtert-Butylbenzene

Answer: A, C, D

Toluene has one set of side-chain H, giving benzyl chloride. In p-xylene the two methyls are equivalent, giving 4-methylbenzyl chloride. In tert-butylbenzene all nine H are equivalent, giving one product. Ethylbenzene has benzylic and terminal H, so two isomers form.
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