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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6:06 minutes

Problem 45d

Textbook Question

Show how Claisen condensations could be used to make the following compounds.
(d)

Verified step by step guidance

Step 1: Identify the target molecule and recognize that it contains a β-keto ester functional group, which is characteristic of a Claisen condensation product. The molecule has a cyclic ketone and an ester group connected to the same carbon.

Step 2: Determine the starting materials for the Claisen condensation. A Claisen condensation typically involves two esters or one ester and one ketone. In this case, the cyclic ketone (cyclohexanone) and ethyl acetate (CH3COOCH2CH3) are suitable starting materials.

Step 3: Outline the reaction mechanism. The Claisen condensation begins with the deprotonation of the α-hydrogen of ethyl acetate by a strong base, such as sodium ethoxide (NaOEt), to form an enolate ion. This enolate ion then attacks the carbonyl carbon of cyclohexanone, forming a new carbon-carbon bond.

Step 4: Describe the intermediate formed. After the nucleophilic attack, a tetrahedral intermediate is formed, which subsequently collapses to expel the ethoxide ion (CH3CH2O−), resulting in the β-keto ester product.

Step 5: Highlight the final step. The reaction is typically followed by an acidic workup to neutralize the base and stabilize the product. The final compound is the β-keto ester shown in the image, formed through the Claisen condensation of cyclohexanone and ethyl acetate.

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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, leading to the formation of a β-keto ester or a β-dicarbonyl compound. This reaction is crucial for forming carbon-carbon bonds and is widely used in organic synthesis to create complex molecules.

Carbonyl Compounds

Carbonyl compounds, which include aldehydes and ketones, contain a carbon atom double-bonded to an oxygen atom. Their reactivity is significant in organic chemistry, particularly in nucleophilic addition reactions and condensation reactions, such as the Claisen condensation, where they can act as electrophiles.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In the context of the compound shown, the presence of carbonyl groups (C=O) and an ethoxy group (–OCH2CH3) indicates potential sites for reactivity and transformation, which are essential for understanding how to synthesize the compound through Claisen condensation.

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Related Practice

Textbook Question

Show how crossed Claisen condensations could be used to prepare the following esters.

(b)

Textbook Question

Show how Claisen condensations could be used to make the following compounds.

(a)

Textbook Question

Show how Claisen condensations could be used to make the following compounds.

(b)

Textbook Question

Show how Claisen condensations could be used to make the following compounds.

(c)

Textbook Question

Predict the products of the following Claisen condensations.

(a)

(b)

Textbook Question

There are other condensation reactions similar to the aldol and Claisen condensations:

a. The Perkin condensation is the condensation of an aromatic aldehyde and acetic anhydride. Draw the product obtained from the following Perkin condensation:

Textbook Question

What product is obtained when the product of a Knoevenagel condensation is heated in an aqueous acidic solution?

Textbook Question

There are other condensation reactions similar to the aldol and Claisen condensations:

c. The Knoevenagel condensation is the condensation of an aldehyde or a ketone that has no a-hydrogens and a compound such as diethyl malonate that has an a-carbon flanked by two electron-withdrawing groups. Draw the product obtained from the following Knoevenagel condensation:

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Show how Claisen condensations could be used to make the following compounds.(d)

Key Concepts

Claisen Condensation

Carbonyl Compounds

Functional Groups

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Show how Claisen condensations could be used to make the following compounds.
(d)