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

Provide the major product after each step for the following reaction.

Major product of enamine alkylation showing an alcohol functional group.

Intermediate product of enamine alkylation with a carbonyl group.

Final product of enamine alkylation with a carbonyl group.

Product of enamine alkylation with a hydroxyl group.

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Verified step by step guidance

Step 1: Analyze the first reaction where acetone reacts with an amine in the presence of an acid catalyst (H⁺). This is a typical example of imine formation. The carbonyl group of acetone will react with the amine to form an imine, with the loss of water.

Step 2: In the second step, the imine formed will react with an alkyl halide (bromopentane) in a nucleophilic substitution reaction. The nitrogen of the imine acts as a nucleophile and attacks the electrophilic carbon of the alkyl halide, leading to the formation of a new carbon-nitrogen bond.

Step 3: The final step involves hydrolysis of the imine under acidic conditions (H₃O⁺). This will convert the imine back to a carbonyl compound, specifically a ketone, by breaking the carbon-nitrogen bond and adding water across it.

Step 4: Consider the structure of the final ketone product. The hydrolysis will result in the formation of a ketone with the alkyl group from the alkyl halide attached to the carbonyl carbon.

Step 5: Review the overall transformation from acetone to the final ketone product, ensuring that the alkyl group from the alkyl halide is correctly positioned in the final structure.