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

25. Condensation Chemistry

Claisen Condensation

Organic Chemistry

25. Condensation Chemistry

Claisen Condensation

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Problem 38c

Textbook Question

Show what esters would undergo Claisen condensation to give the following β-keto esters.
(c)

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Identify the β-keto ester product structure. A β-keto ester contains a ketone group (C=O) at the β-position relative to the ester group (-COOR). Analyze the given β-keto ester to determine the two fragments that could combine during the Claisen condensation.

Recall the mechanism of the Claisen condensation. It involves the reaction of two ester molecules in the presence of a strong base (commonly an alkoxide base) to form a β-keto ester. One ester acts as the nucleophile, and the other acts as the electrophile.

Determine the nucleophilic ester. The nucleophile is the ester that loses an α-hydrogen to form an enolate ion. Identify the ester fragment in the β-keto ester that could form the enolate ion by deprotonation at the α-carbon.

Determine the electrophilic ester. The electrophile is the ester that undergoes nucleophilic acyl substitution. Identify the ester fragment in the β-keto ester that could act as the electrophile during the condensation reaction.

Combine the nucleophilic and electrophilic esters. Write the structures of the two esters that would react in the Claisen condensation to form the given β-keto ester. Ensure that the α-carbon of the nucleophilic ester aligns with the carbonyl carbon of the electrophilic ester in the product.

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Key Concepts

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

Claisen Condensation

Claisen condensation is a reaction between two esters or an ester and a carbonyl compound in the presence of a strong base, typically sodium ethoxide. This reaction results in the formation of a β-keto ester or a β-diketone. The mechanism involves the deprotonation of an alpha hydrogen, leading to the formation of an enolate ion, which then attacks the carbonyl carbon of another ester.

β-Keto Esters

β-Keto esters are organic compounds that contain both a ketone and an ester functional group, with the ketone located at the beta position relative to the ester. They are important intermediates in organic synthesis and can undergo further reactions, such as decarboxylation or hydrolysis, to yield various useful products. Understanding their structure helps in predicting their reactivity in Claisen condensation.

Enolate Ion

An enolate ion is a resonance-stabilized anion formed by the deprotonation of an alpha carbon adjacent to a carbonyl group. This species is crucial in nucleophilic addition reactions, such as Claisen condensation, where it acts as a nucleophile. The stability of the enolate ion influences the reaction pathway and the products formed, making it essential to understand in the context of ester reactions.

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Show what esters would undergo Claisen condensation to give the following β-keto esters. (c)

Key Concepts

Claisen Condensation

β-Keto Esters

Enolate Ion

Watch next

Show what esters would undergo Claisen condensation to give the following β-keto esters.
(c)