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JEE Advanced levelSingle correct optionDifficulty 3 of 3hx105

3-Bromotoluene (m-bromotoluene) is treated with in liquid , and the amines formed through all possible benzyne intermediates are isolated. Counting positional isomers of toluidine, the number of different amines formed is

  1. A3
  2. B2
  3. C1
  4. D4

Answer: A

Loss of using the hydrogen at C-2 gives 3-methylbenzyne (triple bond C-2/C-3) and using the hydrogen at C-4 gives 4-methylbenzyne (triple bond C-3/C-4). Amide addition to 3-methylbenzyne gives 2-methylaniline and 3-methylaniline; addition to 4-methylbenzyne gives 3-methylaniline and 4-methylaniline. The distinct products are o-, m- and p-toluidine, that is 3.
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