Aromatic Amine Basicity
Mediumchemistry
Aniline is less basic than methylamine due to:
Select the correct option:
Solution
Incorrect! Answer:
Resonance delocalization of lone pair into ring
- Definition: Basicity depends on the availability of the lone pair of electrons on the Nitrogen atom.
- Methylamine: The methyl group increases electron density on Nitrogen via the +I effect.
- Aniline: The lone pair on Nitrogen is in conjugation with the π-electrons of the benzene ring.
- Mechanism: Through resonance, the lone pair is delocalized into the ortho and para positions of the ring.
- Consequence: The electrons are 'busy' within the ring and are less available for protonation. Additionally, the anilinium ion (C6H5NH3+) lacks resonance stabilization, making it less stable compared to the parent aniline.
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About This Question
- Subject
- chemistry
- Chapter
- nitrogen organics
- Topic
- aromatic amine basicity
- Difficulty
- Medium
- Year
- 2025
Solution
Correct Answer:
Resonance delocalization of lone pair into ring
- Definition: Basicity depends on the availability of the lone pair of electrons on the Nitrogen atom.
- Methylamine: The methyl group increases electron density on Nitrogen via the +I effect.
- Aniline: The lone pair on Nitrogen is in conjugation with the π-electrons of the benzene ring.
- Mechanism: Through resonance, the lone pair is delocalized into the ortho and para positions of the ring.
- Consequence: The electrons are 'busy' within the ring and are less available for protonation. Additionally, the anilinium ion (C6H5NH3+) lacks resonance stabilization, making it less stable compared to the parent aniline.
This medium difficulty chemistry question is from the chapter nitrogen organics, covering the topic of aromatic amine basicity. It appeared in the 2025 exam.
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