Haloalkanes and Haloarenes · Class 12 · CBSE · Science Chemistry

Chlorobenzene is extremely less reactive towards nucleophilic substitution compared to chloromethane. Which of the following is NOT a valid reason fo…

Practice question from Haloalkanes and Haloarenes (Class 12 · CBSE · Science Chemistry), with the correct answer and a step-by-step solution.

hard · MCQ · Q-9BB267

Chlorobenzene is extremely less reactive towards nucleophilic substitution compared to chloromethane. Which of the following is NOT a valid reason for this?

  1. A.Resonance stabilization of chlorobenzene
  2. B.sp2sp^2 hybridized carbon attached to chlorine in chlorobenzene
  3. C.Instability of the phenyl cation formed during SN1S_N1 mechanism
  4. D.Repulsion between the approaching nucleophile and the positively charged carbon atomCorrect answer

Solution

In haloarenes, the carbon atom attached to chlorine is actually neutral or carries a partial positive charge, and nucleophiles are attracted to it, not repelled by a positively charged carbon. The true reasons for low reactivity include resonance effect (partial double bond character of C-Cl), sp2sp^2 hybridization of carbon (stronger C-Cl bond), and instability of the phenyl cation.

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