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-Schmidt Condensation

Organic Chemistry

25. Condensation Chemistry

Claisen-Schmidt Condensation

Previous problemNext problem

3:12 minutes

Problem 26

Textbook Question

What two carbonyl compounds are required for the synthesis of morachalcone A, via a Claisen–Schmidt condensation?
<IMAGE>

Verified step by step guidance

Understand the Claisen–Schmidt condensation: This reaction involves the condensation of an aldehyde or ketone with another carbonyl compound in the presence of a base to form an α,β-unsaturated carbonyl compound. Typically, one of the reactants lacks an α-hydrogen to prevent self-condensation.

Analyze the structure of morachalcone A: Morachalcone A is a chalcone, which is an α,β-unsaturated ketone. It has a conjugated system with a double bond between the α and β carbons and a ketone group on the β carbon. Identify the two fragments that could combine to form this structure.

Determine the aromatic aldehyde: The aromatic ring attached to the α-carbon in morachalcone A suggests that one of the starting materials is an aromatic aldehyde. Identify the specific aldehyde based on the substituents on the aromatic ring in morachalcone A.

Determine the ketone: The ketone group in morachalcone A indicates that the second starting material is a ketone. The structure of morachalcone A will help you identify the specific ketone required for the reaction.

Combine the two carbonyl compounds: Write the reaction mechanism for the Claisen–Schmidt condensation, showing the base-catalyzed deprotonation of the ketone to form an enolate ion, followed by nucleophilic attack on the aldehyde, and finally dehydration to form the α,β-unsaturated ketone (morachalcone A).

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Claisen–Schmidt Condensation

The Claisen–Schmidt condensation is a reaction between an aldehyde and a ketone in the presence of a base, leading to the formation of an α,β-unsaturated carbonyl compound. This reaction involves the nucleophilic attack of the enolate ion derived from one carbonyl compound on the carbonyl carbon of the other, followed by dehydration. Understanding this mechanism is crucial for identifying the specific carbonyl compounds needed for synthesizing morachalcone A.

Carbonyl Compounds

Carbonyl compounds are organic molecules that contain a carbon atom double-bonded to an oxygen atom (C=O). They include aldehydes, ketones, and carboxylic acids, each with distinct reactivity patterns. In the context of the Claisen–Schmidt condensation, recognizing the types of carbonyl compounds involved is essential for predicting the products and understanding the synthesis of complex molecules like morachalcone A.

Morachalcone A

Morachalcone A is a specific type of flavonoid compound known for its biological activity and potential therapeutic applications. Its synthesis often involves strategic reactions, such as the Claisen–Schmidt condensation, to construct its carbon skeleton. Identifying the correct carbonyl precursors is vital for successfully synthesizing morachalcone A and understanding its structural features and functions.

Previous problemNext problem

2:10m

Watch next

Master Claisen-Schmidt Reaction with a bite sized video explanation from Johnny

Start learning