Which of the following compounds has difficulty in breaking of $\mathrm{C}-\mathrm{X}$ bond during…

Which of the following compounds has difficulty in breaking of $\mathrm{C}-\mathrm{X}$ bond during nucleophilic substitution reaction?
  1. o-Nitrochlorobenzene
  2. p-Nitrochlorobenzene
  3. m-Nitrochlorobenzene
  4. 2,4,6-Trinitrochlorobenzene

Solution

Greater the number of electron withdrawing groups at $\mathrm{o} / \mathrm{p}$ position, greater is the reactivity towards nucleophilic substitution reaction. Electron withdrawing group at meta position has practically no effect on reactivity. Hence, among the given, m-nitrochlorobenzene has difficulty in breaking of $\mathrm{C}-\mathrm{X}$ bond during nucleophilic substitution.

Asked in: MHT CET 2023 (12 May Shift 2)

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