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

16. Conjugated Systems

Claisen Rearrangement

Organic Chemistry

16. Conjugated Systems

Claisen Rearrangement

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15:27 minutes

Problem 41c

Textbook Question

Predict the product of the Claisen reactions shown.
(c)

Verified step by step guidance

Identify the reactants involved in the Claisen reaction. Typically, a Claisen condensation involves two ester molecules or an ester and a ketone.

Determine the base used in the reaction. Commonly, a strong base like sodium ethoxide (NaOEt) is used to deprotonate the alpha hydrogen of the ester.

Recognize the formation of the enolate ion. The base abstracts an alpha hydrogen from the ester, forming an enolate ion, which is a key intermediate in the Claisen condensation.

Consider the nucleophilic attack. The enolate ion acts as a nucleophile and attacks the carbonyl carbon of another ester molecule, leading to the formation of a tetrahedral intermediate.

Identify the final product. The tetrahedral intermediate collapses, resulting in the elimination of an alkoxide ion and forming a β-keto ester as the final product of the Claisen condensation.

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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 where two esters or one ester and a ketone react in the presence of a strong base to form a β-keto ester or a β-diketone. The reaction involves the formation of an enolate ion from one of the ester molecules, which then attacks the carbonyl carbon of another ester, leading to the formation of a new carbon-carbon bond.

Enolate Ion Formation

Enolate ions are formed when a strong base deprotonates the α-hydrogen of an ester or ketone, resulting in a resonance-stabilized anion. This ion is nucleophilic and can attack electrophilic centers, such as the carbonyl carbon in Claisen condensation, facilitating the formation of new carbon-carbon bonds.

Product Prediction in Claisen Reaction

Predicting the product of a Claisen reaction involves identifying the nucleophilic enolate ion and the electrophilic carbonyl carbon. The enolate ion attacks the carbonyl carbon, forming a new C-C bond and resulting in a β-keto ester or β-diketone. Understanding the structure of reactants and the mechanism helps in predicting the final product accurately.

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Related Practice

Textbook Question

Only after working Assessment 22.53, predict the product of the following reactions.

(b)

Textbook Question

The Johnson–Claisen reaction is a variant of the Claisen reaction studied in this chapter. (a) Suggest a mechanism for the first step. (b) Predict the product (B) that would result from heating intermediate A.

Textbook Question

The Eschenmoser–Claisen reaction is a variant of the Claisen reaction studied in this chapter. Based on your answers to Assessments 22.53–22.55, predict a product of this reaction.

Multiple Choice

Predict the major, organic product for the following reaction.

Textbook Question

Predict the product of the Claisen reactions shown.

(b)

Textbook Question

Propose a mechanism for the following reaction:

Textbook Question

If the terminal sp² carbon of the substituent attached to the benzene ring is labeled with ¹⁴C, where will the label be in the product?

Textbook Question

Draw the product of the following reaction:

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