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JEE Main levelSingle correct optionDifficulty 2 of 3o3183

4-Chlorotoluene is treated with in liquid . The amine products are

  1. Aan approximately 1:1 mixture of 3-methylaniline and 4-methylaniline
  2. B4-methylaniline only
  3. C3-methylaniline only
  4. Dan approximately 1:1 mixture of 2-methylaniline and 4-methylaniline

Answer: A

Elimination gives 4-methylbenzyne with the triple bond between C-1 and C-2 (methyl at C-4). Methyl is only weakly directing, so the amide adds to both ends about equally. Addition at C-1 gives 4-methylaniline and at C-2 gives 3-methylaniline, the latter by cine substitution.
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