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Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes

Which of the following compounds is most reactive towards nucleophilic aromatic substitution with NaOMe ?

Correct answer

3

Step-by-step solution

The given reaction is a nucleophilic aromatic substitution ( S _ N Ar ). The reactivity of aryl halides towards S _ N Ar increases with the presence of strong electron-withdrawing groups (such as - NO ₂ ) at the ortho and para positions with respect to the halogen atom. These groups stabilize the intermediate carbanion (Meisenheimer complex) via the -R effect. In 1-fluoro-3,4-dinitrobenzene and 1-chloro-3,4-dinitrobenzene, one - NO ₂ group is at the meta position and the other is at the para position. The meta - NO

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