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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3:33 minutes

Problem 9a

Textbook Question

Predict the reagents or reactant(s) necessary to complete the following syntheses.
(a)

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Identify the target molecule and the functional groups present. The target molecule is an aldehyde with a fluorine substituent and an isopropyl ether group.

Recognize the reagents used in the reaction: DMSO (dimethyl sulfoxide), oxalyl chloride (ClCOCOCl), and triethylamine (Et3N) in dichloromethane (CH2Cl2). This combination is characteristic of the Swern oxidation, which is used to oxidize alcohols to aldehydes or ketones.

Determine the starting material needed for the Swern oxidation. Since the product is an aldehyde, the starting material should be a primary alcohol with the same carbon skeleton as the product.

Analyze the structure of the product to deduce the structure of the starting alcohol. The starting alcohol should have the same carbon framework, with a hydroxyl group replacing the aldehyde group in the product.

Conclude that the starting material is a primary alcohol with the structure: (2R)-2-fluoro-3-methylbutan-1-ol. This alcohol will undergo Swern oxidation to form the desired aldehyde product.

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Key Concepts

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

Swern Oxidation

Swern oxidation is a chemical reaction used to convert primary and secondary alcohols to aldehydes and ketones, respectively. It involves the use of DMSO (dimethyl sulfoxide) activated by oxalyl chloride, followed by a base such as triethylamine (Et3N). This reaction is mild and avoids the use of heavy metals, making it suitable for sensitive substrates.

Stereochemistry

Stereochemistry refers to the spatial arrangement of atoms in molecules and its impact on chemical reactions. In the given synthesis, the presence of a chiral center with a fluorine atom indicates the importance of stereochemical control. Understanding stereochemistry is crucial for predicting the configuration of products in reactions involving chiral centers.

Reagent Selection

Reagent selection is critical in organic synthesis to achieve desired transformations. The choice of DMSO and oxalyl chloride suggests a Swern oxidation, while Et3N acts as a base to neutralize acidic byproducts. Selecting appropriate reagents ensures the reaction proceeds efficiently and yields the intended product with the correct functional groups.

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