Aryl Halides
Chlorobenzene is less reactive than chloroethane towards nucleophilic substitution mainly because:
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About This Question
- Subject
- chemistry
- Chapter
- organic compounds containing halogens
- Topic
- aryl halides
- Difficulty
- Hard
- Year
- 2025
Solution
Correct Answer:
C-Cl bond in chlorobenzene has partial double bond character
In chlorobenzene, lone pair interaction with the aromatic ring gives resonance and partial double bond character to the C-Cl bond. This shortens and strengthens the bond, making cleavage difficult in both SN1 and SN2 pathways. Therefore chlorobenzene is much less reactive than chloroethane toward nucleophilic substitution.
This hard difficulty chemistry question is from the chapter organic compounds containing halogens, covering the topic of aryl halides. It appeared in the 2025 exam.
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