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

Acetoacetic Ester Synthesis

Organic Chemistry

24. Enolate Chemistry: Reactions at the Alpha-Carbon

Acetoacetic Ester Synthesis

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3:58 minutes

Problem 49

Textbook Question

Show the ketones that would result from hydrolysis and decarboxylation of the following β-keto esters.

Verified step by step guidance

Step 1: Understand the reaction mechanism. Hydrolysis of β-keto esters involves breaking the ester bond in the presence of water and acid/base, forming a β-keto acid. Decarboxylation then removes the carboxyl group as CO₂, leaving behind a ketone.

Step 2: Analyze structure (a). The β-keto ester contains a phenyl group (PhCH₂), a methyl group (CH₃), and an ethyl ester group (COOC₂H₅). Hydrolysis will convert the ester group into a carboxylic acid, and decarboxylation will remove the carboxyl group, leaving a ketone with the phenyl and methyl groups attached to the central carbon.

Step 3: Analyze structure (b). The β-keto ester contains a cyclobutane ring, a methyl group (CH₃), and an ethyl ester group (COOCH₂CH₃). Hydrolysis will convert the ester group into a carboxylic acid, and decarboxylation will remove the carboxyl group, leaving a ketone with the cyclobutane ring and methyl group attached to the central carbon.

Step 4: Analyze structure (c). The β-keto ester contains a cyclopentanone ring and an ethyl ester group (OCH₂CH₃). Hydrolysis will convert the ester group into a carboxylic acid, and decarboxylation will remove the carboxyl group, leaving a ketone with the cyclopentanone ring intact.

Step 5: Summarize the results. For each β-keto ester, the hydrolysis and decarboxylation reactions yield a ketone. The specific ketone depends on the substituents attached to the β-keto ester structure. Ensure you understand how the ester group is hydrolyzed and how the carboxyl group is removed during decarboxylation.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

β-Keto Esters

β-keto esters are organic compounds that contain both a ketone and an ester functional group, with the carbonyl of the ketone located at the β position relative to the ester group. This structure allows for unique reactivity, particularly in reactions involving hydrolysis and decarboxylation, which can lead to the formation of ketones. Understanding the structure and reactivity of β-keto esters is crucial for predicting the products of these reactions.

Hydrolysis

Hydrolysis is a chemical reaction involving the breakdown of a compound by water, often resulting in the formation of an alcohol and a carboxylic acid from esters. In the context of β-keto esters, hydrolysis can lead to the release of the ketone and the corresponding carboxylic acid. This reaction is typically catalyzed by acids or bases and is essential for understanding how β-keto esters can be transformed into simpler ketones.

Decarboxylation

Decarboxylation is the process of removing a carboxyl group from a molecule, releasing carbon dioxide (CO2). In the case of β-keto esters, after hydrolysis, the resulting carboxylic acid can undergo decarboxylation, leading to the formation of a ketone. This reaction is significant in organic synthesis as it allows for the generation of ketones from β-keto esters, which are valuable intermediates in various chemical processes.

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