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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4:10 minutes

Problem 68b

Textbook Question

Show how you would use an aldol, Claisen, or another type of condensation to make each compound.
(b)

Verified step by step guidance

Step 1: Identify the target molecule and analyze its structure. The compound contains a β-keto ester functional group, which suggests it can be synthesized using a Claisen condensation reaction. The two cyclopentyl groups indicate that the starting materials should include cyclopentanone and ethyl acetate.

Step 2: Select the starting materials. For a Claisen condensation, you need an ester with an α-hydrogen (ethyl acetate) and a ketone (cyclopentanone) that can act as the nucleophile.

Step 3: Set up the reaction conditions. Use a strong base, such as sodium ethoxide (NaOEt), to deprotonate the α-hydrogen of ethyl acetate, forming an enolate ion. This enolate will act as the nucleophile in the reaction.

Step 4: Perform the Claisen condensation. The enolate ion attacks the carbonyl carbon of cyclopentanone, forming a new C-C bond. After the reaction, protonation restores the β-keto ester functional group.

Step 5: Purify the product. After the reaction is complete, the mixture is acidified to neutralize the base and isolate the β-keto ester product. Techniques such as recrystallization or distillation can be used to purify the compound.

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Key Concepts

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

Aldol Condensation

Aldol condensation is a reaction between aldehydes or ketones that contain alpha-hydrogens, leading to the formation of β-hydroxy aldehydes or ketones. This reaction involves the nucleophilic addition of an enolate ion to a carbonyl compound, followed by dehydration to yield an α,β-unsaturated carbonyl compound. It is a key method for forming carbon-carbon bonds and is widely used in organic synthesis.

Claisen Condensation

Claisen condensation is a reaction between two esters or an ester and a carbonyl compound in the presence of a strong base, resulting in the formation of a β-keto ester or a β-diketone. The reaction involves the formation of an enolate ion from one ester, which then attacks the carbonyl carbon of the other ester. This reaction is significant for building complex molecules and is a fundamental reaction in organic chemistry.

Condensation Reactions

Condensation reactions are a class of reactions where two molecules combine to form a larger molecule, typically with the loss of a small molecule such as water or alcohol. In organic chemistry, these reactions are crucial for synthesizing larger, more complex structures from simpler precursors. Understanding the mechanisms and conditions for these reactions is essential for effective synthesis in organic chemistry.

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Show how you would use an aldol, Claisen, or another type of condensation to make each compound. (b)

Key Concepts

Aldol Condensation

Claisen Condensation

Condensation Reactions

Watch next

Show how you would use an aldol, Claisen, or another type of condensation to make each compound.
(b)