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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Problem 50

Textbook Question

Every oxidation is accompanied by a reduction. Identify the species that is reduced in the Swern oxidation in Assessment 13.48.

Verified step by step guidance

Understand the Swern oxidation: It is a chemical reaction used to convert primary and secondary alcohols to aldehydes and ketones, respectively, using dimethyl sulfoxide (DMSO) and oxalyl chloride (COCl₂) in the presence of a base like triethylamine.

Identify the role of DMSO: In the Swern oxidation, DMSO acts as the oxidizing agent. It is converted to a sulfonium ion intermediate during the reaction.

Recognize the reduction process: During the Swern oxidation, DMSO is reduced to dimethyl sulfide (DMS), which is the species that is reduced in this reaction.

Consider the overall reaction: The alcohol is oxidized to an aldehyde or ketone, while DMSO is reduced to DMS. This demonstrates the principle that every oxidation is accompanied by a reduction.

Review the mechanism: The mechanism involves the formation of an activated DMSO complex, which facilitates the transfer of oxygen from DMSO to the alcohol, resulting in the reduction of DMSO to DMS.

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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 into aldehydes and ketones, respectively. It involves the use of dimethyl sulfoxide (DMSO) activated by oxalyl chloride, followed by the addition of a base like triethylamine. Understanding the reagents and the mechanism is crucial for identifying the species involved in the oxidation and reduction processes.

Oxidation-Reduction (Redox) Reactions

Redox reactions involve the transfer of electrons between two species, where one species is oxidized (loses electrons) and the other is reduced (gains electrons). In the context of Swern oxidation, identifying the species that undergoes reduction is essential, as it complements the oxidation of the alcohol substrate. Recognizing electron transfer and changes in oxidation states is key to understanding these reactions.

Role of Dimethyl Sulfoxide (DMSO)

In Swern oxidation, DMSO acts as the oxidizing agent, facilitating the conversion of alcohols to carbonyl compounds. During the reaction, DMSO is reduced to dimethyl sulfide, which is the species that gains electrons. Understanding the transformation of DMSO and its role in the mechanism helps in identifying the reduced species in the reaction.

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Related Practice

Textbook Question

Give the structure of the principal product(s) when each of the following alcohols reacts with (1) Na₂Cr₂O₇/H₂SO₄, (2) PCC, (3) DMP, and (4) 1 equiv NaOCl-TEMPO.

a. octan-1-ol

b. octan-3-ol

Textbook Question

Predict the products you expect when the following starting material undergoes oxidation with an excess of each of the reagents shown below.

a. chromic acid

b. PCC (pyridinium chlorochromate)

c. sodium hypochlorite/acetic acid

Textbook Question

Predict the products formed by periodic acid cleavage of the following diols.

(a) CH₃CH(OH)CH(OH)CH₃

(b)

Textbook Question

Predict the product of the oxidation reactions shown.

(a)

Textbook Question

Although trans-diols in rings cannot be cleaved using HIO₄ acyclic trans-diols can. Explain this discrepancy.

Textbook Question

Predict the product of the following oxidation reactions.

(b)

Textbook Question

δ-Hydroxyaldehydes are in equilibrium with their hemiacetal form. Predict the product that would form upon treatment of the hemiacetal with Dess–Martin periodinane.

Textbook Question

Tertiary (3°)alcohols are not oxidized by chromic acid. Why?

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