Textbook Question
What products are obtained when the following tertiary amines react with hydrogen peroxide followed by heat?
c.
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Ch. 19 - More About Amines • Reactions of Heterocyclic 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. 19 - More About Amines • Reactions of Heterocyclic CompoundsProblem 32d
Bruice 8th EditionCh. 19 - More About Amines • Reactions of Heterocyclic CompoundsProblem 32dChapter 20, Problem 32d
What products are obtained when the following tertiary amines react with hydrogen peroxide followed by heat?
d. 
Verified step by step guidance1
Step 1: Recognize the structure of the given compound. The molecule is a tertiary amine with a nitrogen atom bonded to three alkyl groups: an ethyl group, a methyl group, and a cyclohexyl group.
Step 2: Understand the reaction mechanism. When tertiary amines react with hydrogen peroxide (H₂O₂), the nitrogen undergoes oxidation to form an amine oxide. This is a nucleophilic substitution reaction where the lone pair on nitrogen attacks the oxygen of H₂O₂.
Step 3: After the formation of the amine oxide, heating the compound leads to a Cope elimination reaction. In this reaction, the amine oxide undergoes a syn-elimination to produce an alkene and a hydroxylamine.
Step 4: Identify the possible products of the Cope elimination. The elimination occurs in such a way that the hydrogen atom and the leaving group (amine oxide) are removed from adjacent carbon atoms, forming a double bond in the cyclohexane ring.
Step 5: Predict the final products. The major product will be the alkene formed in the cyclohexane ring, and the hydroxylamine (CH₂CH₃-N-OH) will be the byproduct. The position of the double bond in the cyclohexane ring depends on the stereochemistry and the most stable configuration.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Tertiary Amines
Tertiary amines are organic compounds that contain a nitrogen atom bonded to three carbon-containing groups. They are characterized by their ability to act as bases and nucleophiles due to the lone pair of electrons on the nitrogen. In reactions, tertiary amines can undergo oxidation, which is relevant when considering their behavior in the presence of oxidizing agents like hydrogen peroxide.
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Naming Secondary and Tertiary Amines
Hydrogen Peroxide as an Oxidizing Agent
Hydrogen peroxide (H2O2) is a powerful oxidizing agent that can facilitate various chemical reactions, including the oxidation of amines. When tertiary amines react with hydrogen peroxide, they can form N-oxides, which are important intermediates in organic synthesis. Understanding this reaction is crucial for predicting the products formed when heat is applied.
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Cope Elimination
Cope elimination is a reaction mechanism that involves the elimination of a leaving group from a tertiary amine, typically resulting in the formation of an alkene. This process often occurs under heat and can lead to the generation of double bonds in the product. Recognizing the conditions that favor Cope elimination is essential for predicting the final products of the reaction involving the tertiary amine and hydrogen peroxide.
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Related Practice
Textbook Question
The chemical shifts of the C-2 hydrogen in the spectra of pyrrole, pyridine, and pyrrolidine are 2.82 ppm, 6.42 ppm, and 8.50 ppm. Match each heterocycle with its chemical shift.
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Textbook Question
b. At what position does pyridine-N-oxide undergo electrophilic aromatic substitution?
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Textbook Question
What products are obtained when the following tertiary amines react with hydrogen peroxide followed by heat?
a.
b.
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Textbook Question
A tertiary amine reacts with hydrogen peroxide to form a tertiary amine oxide.
Tertiary amine oxides undergo a reaction similar to the Hofmann elimination reaction (Section 10.10), called a Cope elimination. In this reaction, a tertiary amine oxide, rather than a quaternary ammonium ion, undergoes elimination. A strong base is not needed for a Cope elimination because the amine oxide acts as its own base.
Does the Cope elimination have an alkene-like transition state or a carbanion-like transition state?
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Textbook Question
a. Draw resonance contributors to show why pyridine-N-oxide is more reactive than pyridine toward electrophilic aromatic substitution.
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