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
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Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
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Table of contents
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 1)31
- Ch. 1 - Remembering General Chemistry: Electronic Structure and Bonding (Part 2)65
- Ch. 2 - Acids and Bases: Central to Understanding Organic Chemistry84
- Ch. 3 - An Introduction to Organic Compounds:Nomenclature, Physical Properties, and Structure183
- Ch. 4 - Isomers: The Arrangement of Atoms in Space121
- Ch. 5 - Alkenes: Structure, Nomenclature, and an Introduction to Reactivity • Thermodynamics and Kinetics83
- Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions175
- Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis119
- Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene148
- Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides212
- Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds131
- Ch. 11 - Organometallic Compounds60
- Ch. 12 - Radicals90
- Ch. 13 - Mass Spectrometry; Infrared Spectroscopy; UV/Vis Spectroscopy62
- Ch. 14 - NMR Spectroscopy95
- Ch. 15 - Reactions of Carboxylic Acids and Carboxylic Acid Derivatives123
- Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives141
- Ch. 17 - Reactions at the Alpha-Carbon101
- Ch. 18 - Reactions of Benzene and Substituted Benzenes144
- Ch. 19 - More About Amines • Reactions of Heterocyclic Compounds49
- Ch. 20 - The Organic Chemistry of Carbohydrates80
- Ch. 21 - Amino Acids, Peptides, and Proteins57
- Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions35
- Ch. 23 - The Organic Chemistry of the Coenzymes—Compounds Derived from Vitamins1
- Ch. 28 - Pericyclic Reactions58
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Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 22c(1,2,3)
Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 22c(1,2,3)Chapter 11, Problem 22c(1,2,3)
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 guidance1
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.
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Strong oxidizing agents
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.
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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
What alcohol would you treat with phosphorus oxychloride and pyridine to form each of the following alkenes?
a.
b.
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Textbook Question
What are the major products obtained when each of the following ethers is heated with one equivalent of HI?
e.
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Textbook Question
If the compound shown in the margin is heated in the presence of H2SO4,
a. what constitutional isomer would be formed in greatest yield?
b. what stereoisomer would be formed in greater yield?
1557
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Textbook Question
What are the major products obtained when each of the following ethers is heated with one equivalent of HI?
c.
d.
1128
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Textbook Question
What are the major products obtained when the following ether is heated with one equivalent of HI?
861
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