Aniline
Aniline is less basic than methylamine because:
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About This Question
- Subject
- chemistry
- Chapter
- organic compounds containing nitrogen
- Topic
- aniline
- Difficulty
- Easy
- Year
- 2025
Solution
Correct Answer:
Lone pair on N is delocalized in benzene ring
Aniline is a weaker base than aliphatic amines (like methylamine) due to the Resonance Effect.
- In aniline (C6H5NH2), the lone pair of electrons on the nitrogen atom is in conjugation with the π-electron system of the benzene ring.
- Through resonance, the electron density is delocalized over the ring, making the lone pair less available for coordination with a proton (H+).
- Furthermore, the anilinium ion formed after protonation has fewer resonance structures than aniline itself, making it comparatively unstable.
- Aliphatic amines have no such resonance and instead benefit from the +I effect of the alkyl group.
This easy difficulty chemistry question is from the chapter organic compounds containing nitrogen, covering the topic of aniline. It appeared in the 2025 exam.
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