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

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Enamine Alkylation and Acylation

Organic Chemistry

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Enamine Alkylation and Acylation

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Multiple Choice

Which is NOT a reason why enamines are good nucleophiles.

Nitrogen is less electronegative than oxygen.

The second-best resonance contributor shows an anion on the α-carbon.

Nitrogen is a base.

Nitrogen is a good electron-donating group.

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Verified step by step guidance

Understand the structure of enamines: Enamines are compounds containing a nitrogen atom bonded to a carbon-carbon double bond. This structure allows for resonance, which is key to their nucleophilic behavior.

Consider the electronegativity of nitrogen: Nitrogen is less electronegative than oxygen, which means it holds onto its electrons less tightly, making it more willing to donate electrons and act as a nucleophile.

Analyze resonance contributors: The second-best resonance structure of an enamine places a negative charge on the α-carbon, enhancing its nucleophilicity by stabilizing the negative charge through resonance.

Evaluate the role of nitrogen as a base: While nitrogen can act as a base, this property does not directly contribute to the nucleophilicity of enamines. Instead, it is the electron-donating ability of nitrogen that enhances nucleophilicity.

Assess the electron-donating ability of nitrogen: Nitrogen's ability to donate electrons makes enamines good nucleophiles, as it increases the electron density on the carbon-carbon double bond, facilitating nucleophilic attack.