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NEET CHEMISTRYMedium

Which of the following compounds undergoes nucleophilic substitution reaction most easily?

A

pp-Methylchlorobenzene

B

pp-Nitrochlorobenzene

C

mm-Nitrochlorobenzene

D

Chlorobenzene

Step-by-Step Solution

Haloarenes (like chlorobenzene) are generally very unreactive towards nucleophilic substitution reactions due to resonance stabilization and the partial double-bond character of the C-Cl\text{C-Cl} bond. However, their reactivity increases significantly if an electron-withdrawing group (EWG) such as NO2-\text{NO}_2 is present at the ortho or para positions . The NO2-\text{NO}_2 group at the para position withdraws electron density via both strong I-I (inductive) and R-R (resonance) effects, making the halogen-bearing carbon more electrophilic and stabilizing the intermediate carbanion formed during the reaction. In contrast, an NO2-\text{NO}_2 group at the meta position only exerts a I-I effect, which provides less stabilization, and an electron-donating group like CH3-\text{CH}_3 decreases reactivity. Therefore, pp-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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