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JEE Main levelOne or more correct optionsDifficulty 2 of 3hx102

Which of the following factors contribute to the low reactivity of chlorobenzene toward nucleophilic substitution (SN1 or SN2)?

  1. AResonance gives the C-Cl bond partial double bond character.
  2. BThe C-Cl bond involves an carbon and is shorter and stronger than in an alkyl chloride.
  3. CThe phenyl cation that SN1 would need is very unstable.
  4. DThe effect of chlorine makes the ring carbons electron rich and repels nucleophiles strongly.

Answer: A, B, C

Resonance and hybridisation strengthen the C-Cl bond, and the phenyl cation has an empty orbital in the plane of the ring, not stabilised by the pi system. The effect of Cl withdraws, not donates, electron density, so the fourth statement is false.
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