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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1:58 minutes

Problem 65b

Textbook Question

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

b. What compound is formed if water is added to the product of a Perkin condensation?

Verified step by step guidance

Step 1: Understand the Perkin condensation reaction. It involves the reaction of an aromatic aldehyde with an anhydride in the presence of a base to form an α,β-unsaturated carboxylic acid derivative.

Step 2: Analyze the product of the Perkin condensation shown in the image. The product is an α,β-unsaturated carboxylic acid derivative with a conjugated double bond system.

Step 3: Consider the addition of water to the product. Water can hydrolyze the double bond in the α,β-unsaturated system under certain conditions, leading to hydration at the β-carbon.

Step 4: The hydration reaction typically forms a β-hydroxy carboxylic acid. This occurs because water adds across the double bond, with the hydroxyl group attaching to the β-carbon and the hydrogen attaching to the α-carbon.

Step 5: The final compound formed after water addition is a β-hydroxy derivative of the original α,β-unsaturated carboxylic acid. This transformation is a key step in understanding the reactivity of α,β-unsaturated systems in organic chemistry.

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Key Concepts

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

Perkin Condensation

The Perkin condensation is a reaction between an aromatic aldehyde and an anhydride, typically yielding α,β-unsaturated carboxylic acids. This reaction involves the formation of a carbon-carbon bond through the nucleophilic attack of the enolate ion derived from the anhydride on the carbonyl carbon of the aldehyde, followed by dehydration to form the final product.

Hydrolysis

Hydrolysis is a chemical reaction involving the breaking of a bond in a molecule using water. In the context of the Perkin condensation product, adding water can lead to the conversion of the α,β-unsaturated carboxylic acid into its corresponding carboxylic acid and alcohol, effectively reversing the condensation process and yielding more stable products.

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. In organic chemistry, these reactions are crucial for forming complex structures and are foundational in synthesizing various organic compounds, including those formed in aldol and Claisen condensations, as well as the Perkin reaction.

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