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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4:13 minutes

Problem 22c(1,2,3)

Textbook Question

What product is obtained from the reaction of each of the following alcohols with
c. the regents required for a Swern oxidation?
1. 3-pentanol
2. 1-pentanol
3. 2-methyl-2-pentanol

Verified step by step guidance

Identify the type of alcohol in each case (primary, secondary, or tertiary) since the Swern oxidation mechanism depends on the type of alcohol.

Recall that Swern oxidation converts primary alcohols to aldehydes and secondary alcohols to ketones, while tertiary alcohols do not undergo oxidation under these conditions.

For 3-pentanol (a secondary alcohol), predict that it will be oxidized to a ketone. The carbon attached to the hydroxyl group will lose a hydrogen, forming a carbonyl group.

For 1-pentanol (a primary alcohol), predict that it will be oxidized to an aldehyde. The hydroxyl group will be replaced by a carbonyl group, and no further oxidation to a carboxylic acid occurs under Swern conditions.

For 2-methyl-2-pentanol (a tertiary alcohol), note that it will not react under Swern oxidation conditions because tertiary alcohols lack a hydrogen atom on the carbon bearing the hydroxyl group, which is necessary for oxidation.

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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 method used to convert alcohols into aldehydes or ketones using a combination of oxalyl chloride, dimethyl sulfoxide (DMSO), and a base such as triethylamine. This reaction is notable for its mild conditions and selectivity, allowing for the oxidation of primary and secondary alcohols without over-oxidation to carboxylic acids.

Alcohol Classification

Alcohols are classified based on the number of carbon atoms bonded to the carbon bearing the hydroxyl (-OH) group. Primary alcohols have one carbon attached, secondary alcohols have two, and tertiary alcohols have three. This classification is crucial for predicting the products of oxidation reactions, as the structure influences the outcome.

Product Formation in Oxidation

The product of an alcohol oxidation depends on its classification. Primary alcohols typically yield aldehydes, secondary alcohols produce ketones, and tertiary alcohols do not oxidize to carbonyls under Swern conditions. Understanding these transformations is essential for determining the expected products from the given alcohols in the question.

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Related Practice

Textbook Question

Predict the product of the following oxidation reactions.

(c)

Textbook Question

Phenol oxidation can be coupled with other reactions to form new C―C bonds using reactions studied previously. Predict the product of the following series of reactions.

(a)

Textbook Question

The intermediates for the Swern oxidation, a reaction introduced in Section 13.9.4, are shown. Provide the arrow-pushing mechanism that rationalizes the formation of each intermediate and the final product(s).

Textbook Question

What product is obtained from the reaction of each of the following alcohols with

a. H₂CrO₄?

1. 3-pentanol

2. 1-pentanol

3. 2-methyl-2-pentanol

Textbook Question

Predict the major products of the following reactions.

(c)

Textbook Question

Which of the following compounds would give a positive Tollens test? (Remember that the Tollens test involves mild basic aqueous conditions.)

(d) CH₃CH₂CH₂CH₂CH(OH)OCH₃

(e) CH₃CH₂CH₂CH₂CH(OCH₃)₂

(f)

Textbook Question

The following reaction involves a starting material with a double bond and a hydroxy group, yet its mechanism resembles a pinacol rearrangement. Propose a mechanism, and point out the part of your mechanism that resembles a pinacol rearrangement.

Textbook Question

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

(c)

(d)

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