Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

22. Carboxylic Acid Derivatives: NAS

Nucleophilic Acyl Substitution

Organic Chemistry

22. Carboxylic Acid Derivatives: NAS

Nucleophilic Acyl Substitution

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Multiple Choice

Why are amides less electrophilic/reactive than esters?

Nitrogen is a worse electron-withdrawing group through resonance, making the carbonyl carbon less stable.

Nitrogen is a better electron-donating group through resonance, making the carbonyl carbon more stable.

Nitrogen is a better electron-withdrawing group through resonance, making the carbonyl carbon more stable.

Nitrogen is a worse electron-donating group through resonance, making the carbonyl carbon less stable.

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Verified step by step guidance

Understand the concept of electrophilicity: Electrophilicity refers to the tendency of a molecule to attract electrons. In carbonyl compounds, the carbon atom is electrophilic due to the polarization of the C=O bond.

Examine the role of resonance in amides: In amides, the nitrogen atom can donate its lone pair of electrons to the carbonyl group, enhancing resonance stabilization. This electron donation reduces the electrophilicity of the carbonyl carbon.

Compare resonance effects in esters: Esters have an oxygen atom adjacent to the carbonyl group. Oxygen is less effective at donating electrons through resonance compared to nitrogen, making the carbonyl carbon in esters more electrophilic.

Analyze the electron-donating ability of nitrogen: Nitrogen is a better electron-donating group through resonance compared to oxygen. This increased electron donation stabilizes the carbonyl carbon in amides, reducing its reactivity.

Conclude why amides are less reactive: Due to the strong resonance stabilization provided by nitrogen, the carbonyl carbon in amides is less electrophilic and more stable, making amides less reactive than esters.