Amide Vs Amine Basicity
Mediumchemistry
Amides are far less basic than amines because:
Select the correct option:
Solution
Incorrect! Answer:
Lone pair delocalized by resonance with carbonyl
- Amine Basicity: In an amine (R−NH2), the lone pair on Nitrogen is localized and available for donation.
- Amide Structure: In an amide (R−CO−NH2), the Nitrogen atom is adjacent to a carbonyl group (C=O).
- Resonance: The lone pair on Nitrogen can be delocalized through resonance into the Oxygen atom (N+=C−O−).
- Consequence: This resonance delocalization significantly reduces the electron density on the Nitrogen atom.
- Basicity: As a result, amides are very weak bases; in fact, they behave as amphoteric substances or very weak acids in certain conditions.
🔒 Solution Hidden from View
Submit your answer to unlock the detailed step-by-step solution.
About This Question
- Subject
- chemistry
- Chapter
- nitrogen organics
- Topic
- amide vs amine basicity
- Difficulty
- Medium
- Year
- 2025
Solution
Correct Answer:
Lone pair delocalized by resonance with carbonyl
- Amine Basicity: In an amine (R−NH2), the lone pair on Nitrogen is localized and available for donation.
- Amide Structure: In an amide (R−CO−NH2), the Nitrogen atom is adjacent to a carbonyl group (C=O).
- Resonance: The lone pair on Nitrogen can be delocalized through resonance into the Oxygen atom (N+=C−O−).
- Consequence: This resonance delocalization significantly reduces the electron density on the Nitrogen atom.
- Basicity: As a result, amides are very weak bases; in fact, they behave as amphoteric substances or very weak acids in certain conditions.
This medium difficulty chemistry question is from the chapter nitrogen organics, covering the topic of amide vs amine basicity. It appeared in the 2025 exam.
Looking for more practice? Explore all chemistry questions or browse nitrogen organics questions on RankGuru.