Amide Vs Amine Basicity
Amides are far less basic than amines because:
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More nitrogen organics Practice Questions
Gas phase basicity order (strongest base first) is typically:
Gas phase basicity order (strongest base first) is typically:
Aniline is less basic than methylamine due to:
Aniline is less basic than methylamine due to:
Diazotization of aniline performed at low temperature (~0–5°C) because:
Diazotization of aniline performed at low temperature (~0–5°C) because:
Hofmann bromamide reaction converts an amide to:
Hofmann bromamide reaction converts an amide to:
Carbylamine test requires chloroform and alcoholic KOH; characteristic product is:
Carbylamine test requires chloroform and alcoholic KOH; characteristic product is:
Reduction of nitrobenzene with Sn/HCl gives initially:
Reduction of nitrobenzene with Sn/HCl gives initially:
Treatment of benzenediazonium chloride with CuCN (Sandmeyer) yields:
Treatment of benzenediazonium chloride with CuCN (Sandmeyer) yields:
Gabriel phthalimide synthesis is used to prepare:
Gabriel phthalimide synthesis is used to prepare:
Diazonium salts couple with phenols in alkaline solution to form:
Diazonium salts couple with phenols in alkaline solution to form:
Primary aliphatic amine treated with nitrous acid evolves:
Primary aliphatic amine treated with nitrous acid evolves:
Primary amine protecting group often formed as sulfonamide using reagent:
Primary amine protecting group often formed as sulfonamide using reagent:
Replacement of diazonium with –OH occurs by heating aqueous solution yielding:
Replacement of diazonium with –OH occurs by heating aqueous solution yielding:
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.
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