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Question

In the question arrange the compounds in increasing order of rate of reaction towards nucleophilic substitution.

(a) (i) < (ii) < (iii) (b) (iii) < (ii) < (i) (c) (i) < (iii) < (ii) (d) (iii) < (i) < (ii)

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Solution

The bond formed between C of the benzene ring and halogen is more stable because of resonance it has partial double bond character. So, the rate of reaction towards nucleophilic substitution is slow. This substitution is facilitated by the presence of electron withdrawing group at ortho and para position because electron density is high at these positions.

Compound (i) and (iii) both have one electron withdrawing group but in compound (ii) electron withdrawing (NO2) group is present at ortho position, so rate of reaction in compound (ii) is more than that of (iii) while (i) has no electron withdrawing group. Hence, the correct option is (c).


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