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