Q36 / 150 · MHT CET 2022 (08 Aug Shift 1) · Chemistry

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

  • A
    O-nitrochlorobenzene
  • B
    P - nitrochlorobenzene
  • Correct answer
    C
    m-nitrochlorobenzene
  • D
    2, 4, 6-trinitrochlorobenzene

Solution

In aryl halide, $\mathrm{X}$ atom is attached with $\mathrm{sp}^2(\mathrm{C})$, the $\mathrm{C}-\mathrm{X}$ bond in aryl halide is shorter than in alkyl halides. This makes $\mathrm{C}-\mathrm{X}$ bond stronger in aryl halides. Under normal conditions, halobenzene's are inert to nucleophiles. However, Chlorobenzene can be made to react if the experimental conditions are: 1. High temperature and high pressure. 2. In presence of strong electron-withdrawing $\left(-\mathrm{NO}_2\right)$ substituent at ortho and/or para positions. Thus, $\mathrm{m}-$ nitrochlorobenzene has difficulty in breaking $\mathrm{C}-\mathrm{X}$ bond.

Hence, the correct answer is option: 'C'.

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