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Question: Answered & Verified by Expert
Arrange the following in the correct order of reactivity towards nucleophilic substitution reaction.
I. 1-chloro-2-nitrobenzene
II. Chlorobenzene
III. 1-chloro-3-nitrobenzene
ChemistryHaloalkanes and HaloarenesTS EAMCETTS EAMCET 2020 (14 Sep Shift 2)
Options:
  • A II > I > III
  • B III > I > II
  • C I > III > II
  • D II > III > I
Solution:
1750 Upvotes Verified Answer
The correct answer is: I > III > II
Presence of $-\mathrm{NO}_2$ group will favour chlorobenzene towards nucleophilic substitution, $\operatorname{ArS}_{\mathrm{N}} 2$ (via addition elimination mechanism) $-R$ effect of $-\mathrm{NO}_2$ at ortho position (I) will favour the reaction most in comparison to $-I$ effect of $-\mathrm{NO}_2$ at meta position (III).


So,the reactivity order : I > III > II .

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