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JEE Main levelSingle correct optionDifficulty 2 of 3hx117

Toluene is converted to and to a mixture of and under two different sets of conditions. The correct pairing is

  1. A with gives the benzyl chloride; with light gives the ring chlorides
  2. B with light gives the ring chlorides; with gives -chlorotoluene
  3. C with gives both the benzyl chloride and the ring chlorides in equal amounts
  4. D with light on boiling toluene gives the benzyl chloride; with in the dark gives the ring chlorides

Answer: D

Under light (radical conditions) the side chain is chlorinated through the stable benzyl radical. With a Lewis acid catalyst in the dark, -type electrophilic substitution occurs on the ring; is an activating ortho/para director, so - and -chlorotoluene result.
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