Textbook Question
Identify the alcohols that would undergo oxidation to produce the following carbonyl compounds.
(b)
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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 51c
Mullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 51cChapter 12, Problem 51c
Identify the alcohols that would undergo oxidation to produce the following carbonyl compounds.
(c) 
Verified step by step guidance1
Identify the carbonyl compound in the image. The structure shown is a ketone, specifically a phenyl-2-propanone.
Recall that ketones are typically formed by the oxidation of secondary alcohols. Therefore, the alcohol precursor must be a secondary alcohol.
Examine the structure of the ketone. The carbonyl group is attached to a phenyl group and a propyl group, indicating that the secondary alcohol must have a hydroxyl group on the carbon that is bonded to both the phenyl and propyl groups.
Determine the structure of the alcohol. The secondary alcohol that would oxidize to form this ketone is 1-phenyl-2-propanol, where the hydroxyl group is on the second carbon of the propyl chain.
Understand the oxidation process. During oxidation, the hydroxyl group of the secondary alcohol is converted into a carbonyl group, resulting in the formation of the ketone shown in the image.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Alcohol Classification
Alcohols are classified into three categories: primary, secondary, and tertiary, based on the number of carbon atoms attached to the carbon bearing the hydroxyl (-OH) group. Primary alcohols can be oxidized to aldehydes, secondary alcohols to ketones, and tertiary alcohols generally do not oxidize to carbonyl compounds due to the lack of a hydrogen atom on the carbon bearing the -OH group.
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Structural Classification
Oxidation Reactions
Oxidation in organic chemistry refers to the process of increasing the oxidation state of a molecule, often involving the addition of oxygen or the removal of hydrogen. In the case of alcohols, oxidation typically converts them into carbonyl compounds, such as aldehydes or ketones, depending on the type of alcohol being oxidized.
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Reagents for Oxidation
Common reagents used for the oxidation of alcohols include potassium dichromate (K2Cr2O7), chromium trioxide (CrO3), and pyridinium chlorochromate (PCC). The choice of reagent can influence the extent of oxidation, with some reagents selectively oxidizing primary alcohols to aldehydes while others may further oxidize them to carboxylic acids.
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Related Practice
Textbook Question
Every oxidation is accompanied by a reduction. Identify the species that is reduced in the Swern oxidation in Assessment 13.48.
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Textbook Question
Predict the product of the oxidation reactions shown.
(a)
Textbook Question
Identify the alcohols that would undergo oxidation to produce the following carbonyl compounds.
(d)
1
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Textbook Question
Predict the product of the oxidation reactions shown.
(b)
5
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Textbook Question
Identify the alcohols that would undergo oxidation to produce the following carbonyl compounds.
(a)