The compound which will have the lowest rate towards nucleophilic aromatic substitution on treatment with \(\mathrm{OH^-}\) is
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The Correct Option is B
Solution and Explanation
The rate depends on how well this negative charge is delocalised. An electron-withdrawing \(\mathrm{-NO_2}\) group stabilises the charge by resonance only when it is at the ortho or para position to Cl.
(A) o-nitro: charge delocalised onto \(\mathrm{-NO_2}\) - fast.
(B) m-nitro: the \(\mathrm{-NO_2}\) is meta, so there is no resonance delocalisation onto it (only a weak inductive effect) - slowest.
(C) p-nitro: charge delocalised onto \(\mathrm{-NO_2}\) - fast.
(D) 2,4-dinitro: two groups (ortho and para) stabilise the intermediate - fastest.
Order of rate: D > C, A > B. The lowest rate is for the meta isomer, compound (B).
Answer: (2) 1-chloro-3-nitrobenzene (compound B)
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