Haloarenes
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
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:
- Resonance Effect: lone pairs on Chlorine are conjugated with the π electrons of the benzene ring. This gives the C−Cl bond partial double bond character, making it shorter and stronger.
- Hybridization: The Carbon in Ph−Cl is sp2 hybridized (more electronegative), while in R−Cl it is sp3. The sp2 carbon holds the electron pair of C−Cl more tightly.
- Repulsion: The electron-rich benzene ring repels incoming nucleophiles.
- Phenyl Cation Instability: SN1 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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