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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o3205

Which of the following give 3-methoxyaniline as the main amine product when treated with in liquid (inductive effect of on the aryne controls the regiochemistry)?

  1. A1-chloro-2-methoxybenzene
  2. B2-bromo-1,3-dimethoxybenzene
  3. C1-bromo-3-methoxybenzene
  4. D1-chloro-4-nitrobenzene

Answer: A, C

For 1-chloro-2-methoxybenzene and 1-bromo-3-methoxybenzene the aryne forms next to the methoxy group, and the amide adds at the carbon meta to OCH3 so that the carbanion sits next to the electronegative oxygen. Both give 3-methoxyaniline. 2-Bromo-1,3-dimethoxybenzene has no ortho hydrogen and cannot form an aryne, and 1-chloro-4-nitrobenzene reacts by SNAr to give 4-nitroaniline.
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