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JEE Main levelSingle correct optionDifficulty 2 of 3hx095

Arrange the following in increasing order of reactivity toward aqueous (nucleophilic aromatic substitution).

  1. A1-chloro-4-nitrobenzene < chlorobenzene < 1-chloro-2,4-dinitrobenzene < 2-chloro-1,3,5-trinitrobenzene
  2. Bchlorobenzene < 1-chloro-4-nitrobenzene < 1-chloro-2,4-dinitrobenzene < 2-chloro-1,3,5-trinitrobenzene
  3. Cchlorobenzene < 1-chloro-2,4-dinitrobenzene < 1-chloro-4-nitrobenzene < 2-chloro-1,3,5-trinitrobenzene
  4. D2-chloro-1,3,5-trinitrobenzene < 1-chloro-2,4-dinitrobenzene < 1-chloro-4-nitrobenzene < chlorobenzene

Answer: B

Ortho and para nitro groups stabilise the negatively charged Meisenheimer complex by resonance, so each additional such group speeds up the reaction. Chlorobenzene has none, then one para nitro, two (2,4) and three (2,4,6). The reactivity therefore increases in that order.
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