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JEE Advanced levelSingle correct optionDifficulty 3 of 3hx036

Consider the following aryl halides toward hot aqueous (nucleophilic aromatic substitution): I, chlorobenzene; II, 1-chloro-4-nitrobenzene; III, 1-chloro-2,4-dinitrobenzene; IV, 2-chloro-1,3,5-trinitrobenzene. The correct order of increasing reactivity is

  1. A
  2. B
  3. C
  4. D

Answer: D

The reaction goes through a negatively charged Meisenheimer intermediate, stabilised by electron-withdrawing groups ortho or para to . Each additional ortho or para group delocalises the charge further. Reactivity therefore rises with the number of ortho and para nitro groups: 0, 1, 2, 3.
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