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Haloarenes

Mediumchemistry

Chlorobenzene is less reactive than chloroethane toward nucleophilic substitution because:

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About This Question

Subject
chemistry
Chapter
organic compounds containing halogens
Topic
haloarenes
Difficulty
Medium
Year
2025
Tags
HaloarenesResonanceLow Reactivity

Solution

Correct Answer:

Both stronger C-Cl bond and resonance

Haloarenes (like chlorobenzene) are remarkably unreactive toward nucleophilic substitution compared to haloalkanes due to several factors:

  1. Resonance Effect: lone pairs on Chlorine are conjugated with the electrons of the benzene ring. This gives the bond partial double bond character, making it shorter and stronger.
  2. Hybridization: The Carbon in is hybridized (more electronegative), while in it is . The carbon holds the electron pair of more tightly.
  3. Repulsion: The electron-rich benzene ring repels incoming nucleophiles.
  4. Phenyl Cation Instability: is impossible as the phenyl cation is highly unstable.

This medium difficulty chemistry question is from the chapter organic compounds containing halogens, covering the topic of haloarenes. It appeared in the 2025 exam.

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