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JEE Advanced levelSingle correct optionDifficulty 3 of 3hx163

3-Chlorotoluene (1-chloro-3-methylbenzene) is treated with in liquid . The number of different methylaniline (toluidine) isomers formed through benzyne intermediates is

  1. A1
  2. B4
  3. C2
  4. D3

Answer: D

Number ring carbons with at C-1 and at C-3. Hydrogens ortho to are at C-2 and C-6, giving two benzynes. The C1-C2 benzyne gives NH2 at C-1 (meta to ) or at C-2 (ortho). The C1-C6 benzyne gives NH2 at C-1 (meta) or at C-6 (para to ). So the o-, m- and p-toluidines are all formed: 3.
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