Amines
Aniline is a weaker base than cyclohexylamine mainly because:
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About This Question
- Subject
- chemistry
- Chapter
- organic compounds containing nitrogen
- Topic
- amines
- Difficulty
- Hard
- Year
- 2025
Solution
Correct Answer:
Lone pair on nitrogen in aniline is delocalized by resonance
Basicity depends on the availability of the nitrogen lone pair for protonation. In aniline, this lone pair interacts with the aromatic ring and gets delocalized through resonance, reducing electron density on nitrogen and lowering basic strength. In cyclohexylamine, the lone pair remains localized and alkyl +I effect pushes electron density toward nitrogen, making protonation easier. Hence cyclohexylamine is stronger as a base.
This hard difficulty chemistry question is from the chapter organic compounds containing nitrogen, covering the topic of amines. It appeared in the 2025 exam.
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