Which of the following compounds undergoes nucleophilic substitution reaction most easily?
-Methylchlorobenzene
-Nitrochlorobenzene
-Nitrochlorobenzene
Chlorobenzene
Haloarenes (like chlorobenzene) are generally very unreactive towards nucleophilic substitution reactions due to resonance stabilization and the partial double-bond character of the bond. However, their reactivity increases significantly if an electron-withdrawing group (EWG) such as is present at the ortho or para positions . The group at the para position withdraws electron density via both strong (inductive) and (resonance) effects, making the halogen-bearing carbon more electrophilic and stabilizing the intermediate carbanion formed during the reaction. In contrast, an group at the meta position only exerts a effect, which provides less stabilization, and an electron-donating group like decreases reactivity. Therefore, -nitrochlorobenzene undergoes nucleophilic substitution most easily . (Note: Options were reconstructed based on the standard AIPMT 2011 question as they were missing in the raw data).
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