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JEE Main levelSingle correct optionDifficulty 2 of 3hc150

Toluene is treated with in sunlight at its boiling point (no Lewis acid). The main monochlorinated product is

  1. A (benzyl chloride)
  2. Bm-chlorotoluene
  3. Co-chlorotoluene
  4. Dp-chlorotoluene

Answer: A

Light and heat favour free radical halogenation at the side chain. The stable benzyl radical forms, giving benzyl chloride. Ring chlorination (o/p) requires in the dark.
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