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

13. Alcohols and Carbonyl Compounds

Oxidizing Agent

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Oxidizing Agent

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3:41 minutes

Problem 36c

Textbook Question

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).
(c) but-2-enal → but-2-enoic acid

Verified step by step guidance

Identify the functional group transformation: The problem involves converting an aldehyde group (-CHO) in but-2-enal to a carboxylic acid group (-COOH) in but-2-enoic acid. This is an oxidation reaction.

Choose an appropriate oxidizing agent: Aldehydes can be oxidized to carboxylic acids using oxidizing agents such as potassium permanganate (KMnO₄), chromium-based reagents (e.g., Jones reagent), or silver oxide (Ag₂O) in aqueous conditions.

Write the reaction mechanism: The aldehyde group in but-2-enal reacts with the oxidizing agent. The carbonyl carbon of the aldehyde is oxidized to form the carboxylic acid group. The double bond in the molecule remains unaffected because the oxidizing agents used are selective for aldehydes.

Ensure reaction conditions are mild: Use aqueous or slightly acidic conditions to facilitate the oxidation without affecting the double bond in the molecule. For example, KMnO₄ in a dilute solution under neutral or slightly basic conditions can be used.

Verify the product: The final product is but-2-enoic acid, which retains the double bond in the molecule while the aldehyde group is converted to a carboxylic acid group. Confirm the structure of the product to ensure the synthesis is complete.

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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 key reaction in organic chemistry where aldehydes or ketones with alpha-hydrogens react in the presence of a base to form β-hydroxy aldehydes or ketones. This reaction can lead to the formation of larger carbon skeletons and is crucial for synthesizing compounds like but-2-enoic acid from but-2-enal through subsequent dehydration.

Oxidation-Reduction Reactions

Oxidation-reduction (redox) reactions involve the transfer of electrons between species, resulting in changes in oxidation states. In the context of converting but-2-enal to but-2-enoic acid, understanding how aldehydes can be oxidized to carboxylic acids is essential, as this transformation typically requires an oxidizing agent.

Reagents and Reaction Conditions

The choice of reagents and reaction conditions is critical in organic synthesis. For the conversion of but-2-enal to but-2-enoic acid, reagents such as potassium permanganate or chromium-based oxidants can be used to facilitate the oxidation process. Understanding the reactivity and selectivity of these reagents helps in designing efficient synthetic pathways.

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