Arrange the following in decreasing order of reactivity towards aqueous $NaOH$ (nucleophilic aromatic substitution): (I) chlorobenzene, (II) 1-chloro-4-nitrobenzene, (III) 1-chloro-2,4-dinitrobenzene, (IV) 2-chloro-1,3,5-trinitrobenzene.

AI $>$ II $>$ III $>$ IV
BII $>$ III $>$ IV $>$ I
CIII $>$ IV $>$ II $>$ I
DIV $>$ III $>$ II $>$ I

Answer: D

Electron-withdrawing

NO X_{2}

groups ortho and para to

Cl

stabilise the anionic Meisenheimer intermediate by delocalising the negative charge. Reactivity grows with the number of such groups: three (IV) > two (III) > one (II) > none (I). Typical conditions are room temperature, 368 K, 433 K and 623 K respectively.

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Arrange the following in decreasing order of reactivity towards aqueous NaOH (nucleophilic aromatic substitution): (I) chlorobenzene, (II) 1-chloro-4-nitrobenzene, (III) 1-chloro-2,4-dinitrobenzene, (IV) 2-chloro-1,3,5-trinitrobenzene.

Answer: D

More questions on Reactions of aryl halides

Arrange the following in decreasing order of reactivity towards aqueous $NaOH$ (nucleophilic aromatic substitution): (I) chlorobenzene, (II) 1-chloro-4-nitrobenzene, (III) 1-chloro-2,4-dinitrobenzene, (IV) 2-chloro-1,3,5-trinitrobenzene.