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

Malonic Ester Synthesis

Organic Chemistry

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Malonic Ester Synthesis

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Multiple Choice

Provide the major product for the following reaction

Structure of a beta-hydroxy acid intermediate in malonic ester synthesis.

Structure of a beta-keto acid intermediate in malonic ester synthesis.

Structure of a different beta-keto acid intermediate in malonic ester synthesis.

Structure of another beta-keto acid intermediate in malonic ester synthesis.

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Verified step by step guidance

The reaction begins with the deprotonation of the alpha carbon of the diethyl malonate by sodium ethoxide (NaOEt) in ethanol (EtOH), forming an enolate ion.

The enolate ion then acts as a nucleophile and attacks the electrophilic carbon in 1-bromopropane (CH3CH2CH2Br), resulting in an alkylation reaction. This step adds a propyl group to the alpha carbon of the diethyl malonate.

Next, the diethyl malonate undergoes hydrolysis in the presence of sodium hydroxide (NaOH) and water (H2O), converting the ester groups into carboxylic acids.

The resulting dicarboxylic acid is then subjected to decarboxylation under acidic conditions (H3O+) and heat, which removes one of the carboxyl groups as carbon dioxide (CO2), leaving behind a mono-carboxylic acid.

The final product is a carboxylic acid with a propyl group attached to the alpha carbon, which is the major product of this reaction sequence.