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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3hx160

Under the conditions: aqueous at or below 368 K (and no catalyst), which of these aryl halides are converted into the corresponding phenol derivative?

  1. Achlorobenzene
  2. B1-chloro-2,4-dinitrobenzene
  3. C2-chloro-1,3,5-trinitrobenzene
  4. D1-chloro-4-methylbenzene

Answer: B, C

2,4-Dinitrochlorobenzene reacts with aqueous at about 368 K and picryl chloride (2-chloro-1,3,5-trinitrobenzene) even at room temperature, because of the activating ortho/para groups. Chlorobenzene needs 623 K and 300 atm, and the methyl group in 4-chlorotoluene is electron-donating, so it is also unreactive under mild conditions.
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