Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes
Identify the correct order of reactivity of the following compounds towards nucleophilic aromatic substitution ( S_NAr ): I. II. III.
Options
- AIII > I > II
- BII > I > III
- CI > III > II
- DI > II > III
Correct answer
B. II > I > III
Step-by-step solution
Nucleophilic aromatic substitution ( S_NAr ) is facilitated by the presence of electron-withdrawing groups (such as - NO₂ ) at the ortho and para positions relative to the leaving group (halogen). These groups stabilize the intermediate carbanion (Meisenheimer complex) through strong -I and -M effects. The greater the number of electron-withdrawing groups at the ortho and para positions, the more stable the intermediate, and consequently, the higher the reactivity of the compound towards S_NAr . Analyzing the given