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JEE Main levelSingle correct optionDifficulty 2 of 3hx154

1-Chloro-4-methylbenzene is treated with in liquid . The number of different aromatic amine products (constitutional isomers) formed is

  1. A2
  2. B1
  3. C3
  4. D4

Answer: A

Loss of from C-2 (ortho to ) and gives a benzyne with the triple bond between C-1 and C-2 ( at C-4). adds to C-1 to give 4-methylaniline (para), or to C-2 to give 3-methylaniline (meta). The other ortho position gives the same pair, so there are 2 products.
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