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JEE Main levelSingle correct optionDifficulty 2 of 3o3184

Which of the following aryl halides cannot give an aryne with in liquid ?

  1. A2-chloro-1,3-dimethylbenzene
  2. B1-chloro-3-methylbenzene
  3. Cchlorobenzene
  4. D1-chloro-4-methylbenzene

Answer: A

Aryne formation needs a hydrogen on a ring carbon adjacent to the carbon bearing the halogen. Both ortho positions of 2-chloro-1,3-dimethylbenzene carry methyl groups and no hydrogen, so elimination cannot occur. The other three halides each have at least one ortho hydrogen.
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