Textbook Question
Identify the alcohols that would undergo oxidation to produce the following carbonyl compounds.
(b)
2
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Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
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Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 50
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 50Chapter 12, Problem 50
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 guidance1
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.
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03:20
Benzylic Oxidation
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.
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06:02General Features of Redox
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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03:51Reagents used to oxidize Sulfides.
Related Practice
Textbook Question
Suggest an alkene that, in two steps, could be converted into each of the following ketones. Each sequence should involve a pinacol rearrangement.
(c)
3
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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).
1
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Textbook Question
In Assessment 13.48, identify the individual step that represents the general mechanism for all alcohol oxidation reactions.
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Textbook Question
Identify the alcohols that would undergo oxidation to produce the following carbonyl compounds.
(c)
Textbook Question
Identify the alcohols that would undergo oxidation to produce the following carbonyl compounds.
(a)