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

Intramolecular Aldol Condensation

Organic Chemistry

25. Condensation Chemistry

Intramolecular Aldol Condensation

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Multiple Choice

How is the Dieckmann reaction different from the Claisen reaction?

The Dieckmann reaction uses lithium diisopropylamide (LDA) as the base, while the Claisen reaction uses an alkoxide as the base.

The Dieckmann reaction is an intramolecular reaction, while the Claisen reaction is intermolecular.

In the Dieckmann reaction, the enolate attacks an aldehyde, while in the Claisen reaction, the enolate attacks an ester.

The Dieckmann is an intramolecular aldol reaction, while the Claisen is an intramolecular Claisen reaction.

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Verified step by step guidance

Understand the basic definitions: The Dieckmann reaction is a type of intramolecular Claisen condensation, where a diester forms a cyclic β-keto ester. The Claisen reaction, on the other hand, is an intermolecular reaction where two ester molecules react to form a β-keto ester.

Identify the type of reaction: The Dieckmann reaction is intramolecular, meaning it occurs within a single molecule, leading to the formation of a ring structure. The Claisen reaction is intermolecular, involving two separate ester molecules.

Examine the role of the base: In the Dieckmann reaction, a strong base like lithium diisopropylamide (LDA) is often used to deprotonate the ester, forming an enolate ion. In the Claisen reaction, an alkoxide base is typically used for the same purpose.

Analyze the nucleophilic attack: In the Dieckmann reaction, the enolate ion generated from one ester group attacks the carbonyl carbon of another ester group within the same molecule, leading to ring closure. In the Claisen reaction, the enolate ion from one ester molecule attacks the carbonyl carbon of a different ester molecule.

Clarify the reaction outcomes: The Dieckmann reaction results in the formation of a cyclic β-keto ester, while the Claisen reaction results in a linear β-keto ester. This difference is due to the intramolecular versus intermolecular nature of the reactions.