Haloalkanes and Haloarenes - Result Question 43

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

[2011 M] (a)O=N+c1ccc(Cl)cc1

(c)COc1ccc(Cl)cc1

(b)Cc1ccc(Cl)cc1

(d)Clc1ccccc1

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Solution:

  1. (a) To compare the rates of substitution, in chlorobenzene, 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 electronreleasing group). G withdraws electrons, neutralises (disperses)ve charge of the ring, stabilises carbanion, facilitates SN reaction (activation effect)

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 reaction is :

In SN reactions, a carbanion 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 SN reactions.



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