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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5:07 minutes

Problem 36d

Textbook Question

Predict the products of self-condensation of the following esters.
(d)

Verified step by step guidance

Step 1: Recognize that the reaction involves self-condensation of esters, which typically occurs via the Claisen condensation mechanism. This reaction requires a base (NaOEt) and an ester with an α-hydrogen.

Step 2: Identify the α-hydrogen in the ester molecule. The α-hydrogen is located on the carbon adjacent to the carbonyl group. In this case, the ester has α-hydrogens available for deprotonation.

Step 3: The base (NaOEt) deprotonates the α-hydrogen, forming an enolate ion. The enolate ion is nucleophilic and can attack the carbonyl carbon of another ester molecule.

Step 4: The nucleophilic enolate ion attacks the carbonyl carbon of another ester molecule, leading to the formation of a tetrahedral intermediate. This intermediate then collapses, expelling the ethoxide ion (EtO⁻) as a leaving group.

Step 5: The final product of the self-condensation reaction is a β-keto ester. The structure of the β-keto ester will include the original ester group and a ketone group separated by one carbon atom.

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Key Concepts

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

Self-Condensation of Esters

Self-condensation of esters involves the reaction of an ester with itself in the presence of a base, leading to the formation of β-keto esters or other products. This reaction typically occurs through the formation of an enolate ion, which then attacks another ester molecule, resulting in a new carbon-carbon bond. Understanding this mechanism is crucial for predicting the products of the reaction.

Enolate Ion Formation

Enolate ions are formed when a base abstracts a proton from the α-carbon of an ester, creating a resonance-stabilized anion. This ion is highly nucleophilic and can attack electrophiles, such as another ester molecule. The stability of the enolate ion is influenced by the structure of the ester and the strength of the base used, which is essential for predicting the outcome of the self-condensation reaction.

Synthesis of β-Keto Esters

The synthesis of β-keto esters is a common outcome of ester self-condensation reactions. In this process, the nucleophilic enolate ion attacks the carbonyl carbon of another ester, leading to the formation of a β-keto ester. This compound features a carbonyl group at the β-position relative to the original ester, and understanding its formation is key to predicting the products of the given reaction.

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