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JEE Advanced levelSingle correct optionDifficulty 3 of 3hx106

Chlorobenzene is nitrated with conc. /conc. , the para isomer is separated and heated with aqueous at 443 K, and the mixture is then acidified. The final product is

  1. A4-chlorophenol
  2. B2,4-dinitrophenol
  3. C3-nitrophenol
  4. D4-nitrophenol

Answer: D

Nitration is ortho/para directing, giving 1-chloro-4-nitrobenzene as the separated para isomer. The para nitro group activates the ring toward nucleophilic substitution, so displaces at 443 K via the Meisenheimer complex to give sodium 4-nitrophenoxide. Acidification gives 4-nitrophenol.
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