Explain the mechanism of nucleophilic substitution reaction of $m$-nitrochlorobenzene at ortho and para positions.
(N/A) The nucleophilic substitution reaction of $m$-nitrochlorobenzene with $HO^-$ follows the addition-elimination mechanism (often referred to as $S_NAr$).
When the $-NO_2$ group is at the ortho or para position,the intermediate carbanion has a special resonance structure $(II)$ where the negative charge is delocalized onto the carbon atom attached to the $-NO_2$ group,allowing the nitro group to stabilize the negative charge through its $-I$ and $-M$ effects.
In the case of $m$-nitrochlorobenzene,none of the resonance structures of the intermediate carbanion place the negative charge on the carbon atom directly attached to the $-NO_2$ group. Therefore,the presence of the $-NO_2$ group at the meta position does not significantly enhance the reactivity of the haloarene towards nucleophilic substitution compared to chlorobenzene.
When the $-NO_2$ group is at the ortho or para position,the intermediate carbanion has a special resonance structure $(II)$ where the negative charge is delocalized onto the carbon atom attached to the $-NO_2$ group,allowing the nitro group to stabilize the negative charge through its $-I$ and $-M$ effects.
In the case of $m$-nitrochlorobenzene,none of the resonance structures of the intermediate carbanion place the negative charge on the carbon atom directly attached to the $-NO_2$ group. Therefore,the presence of the $-NO_2$ group at the meta position does not significantly enhance the reactivity of the haloarene towards nucleophilic substitution compared to chlorobenzene.
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