Textbook Question
What alcohol would you treat with phosphorus oxychloride and pyridine to form each of the following alkenes?
a.
b.
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 22a(1,2,3)
Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 22a(1,2,3)Chapter 11, Problem 22a(1,2,3)
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
Verified step by step guidance1
Step 1: Understand the reagent H₂CrO₄ (chromic acid). It is a strong oxidizing agent commonly used to oxidize alcohols. Primary alcohols are oxidized to carboxylic acids, secondary alcohols are oxidized to ketones, and tertiary alcohols generally do not undergo oxidation under these conditions.
Step 2: Analyze the structure of 3-pentanol. It is a secondary alcohol because the hydroxyl group (-OH) is attached to a carbon atom that is bonded to two other carbon atoms. When treated with H₂CrO₄, secondary alcohols are oxidized to ketones. The product will be a ketone with the same carbon chain length.
Step 3: Analyze the structure of 1-pentanol. It is a primary alcohol because the hydroxyl group (-OH) is attached to a carbon atom that is bonded to only one other carbon atom. When treated with H₂CrO₄, primary alcohols are oxidized first to aldehydes and then further to carboxylic acids. The product will be a carboxylic acid with the same carbon chain length.
Step 4: Analyze the structure of 2-methyl-2-pentanol. It is a tertiary alcohol because the hydroxyl group (-OH) is attached to a carbon atom that is bonded to three other carbon atoms. Tertiary alcohols do not undergo oxidation with H₂CrO₄ because there is no hydrogen atom on the carbon bearing the hydroxyl group to be removed during the oxidation process. Therefore, no reaction occurs.
Step 5: Summarize the expected products: (1) 3-pentanol will yield a ketone (3-pentanone), (2) 1-pentanol will yield a carboxylic acid (pentanoic acid), and (3) 2-methyl-2-pentanol will not react with H₂CrO₄.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Oxidation of Alcohols
Alcohols can undergo oxidation reactions, where they lose electrons and typically gain oxygen or lose hydrogen. The extent of oxidation depends on the type of alcohol: primary alcohols can be oxidized to aldehydes and then to carboxylic acids, secondary alcohols to ketones, and tertiary alcohols generally do not oxidize easily.
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Chromic Acid (H2CrO4) as an Oxidizing Agent
Chromic acid is a strong oxidizing agent commonly used in organic chemistry to oxidize alcohols. It facilitates the conversion of primary and secondary alcohols into their corresponding carbonyl compounds, while tertiary alcohols typically remain unchanged due to steric hindrance and the stability of the tertiary structure.
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Types of Alcohols
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. This classification is crucial for predicting the products of oxidation reactions, as each type reacts differently with oxidizing agents like chromic acid.
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Related Practice
Textbook Question
What stereoisomers are formed in the following reactions? Which stereoisomer is the major product?
b. the acid-catalyzed dehydration of 3,4-dimethyl-3-hexanol to 3,4-dimethyl-3-hexene
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?
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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.
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Textbook Question
What are the major products obtained when the following ether is heated with one equivalent of HI?
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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