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Q.

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

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a

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b

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c

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d

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answer is A.

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Detailed Solution

In SN Ar reactions, acarbanion is formed as an intermediate, so any substituent that increases the stability of carbanion and hence the transition state leading to its formation will enhance the SNAr reactions. To compare the rates of substitution in chlorobenzene, chlorobenzene having electron-withdrawing group, and chlorobenzene having electron-releasing group, we compare the structures carbanion I (from chlorobenzene), II (from chlorobenzene containing electron-withdrawing group) and III (from chlorobenzene containing electron-releasing group). 

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G withdraws electrons, neutralises (disperses) —ve charge of the ring, stabilises carbanion, facilitates SN, reaction (activation effect) 

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G releases electrons, intensifies —ve charge, destabilizes carbanion, retards SN reaction (deactivation) NO2 is activating group and CH3, and OCH3, are deactiving group.Hence, the correct order of nucleophilic substitution reactions 

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