Textbook Question
What products are obtained when the following tertiary amines react with hydrogen peroxide followed by heat?
d.
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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 32c
Bruice 8th EditionCh. 19 - More About Amines • Reactions of Heterocyclic CompoundsProblem 32cChapter 20, Problem 32c
What products are obtained when the following tertiary amines react with hydrogen peroxide followed by heat?
c. 
Verified step by step guidance1
Step 1: Recognize the structure of the given compound. The molecule is a tertiary amine with the nitrogen atom bonded to three alkyl groups: two ethyl groups and one isopropyl group.
Step 2: Understand the reaction mechanism. When a tertiary amine reacts with hydrogen peroxide (H₂O₂), it undergoes oxidation to form an amine oxide. This is a nucleophilic substitution reaction where the lone pair of electrons on the nitrogen attacks the oxygen atom of hydrogen peroxide.
Step 3: Write the intermediate product. The tertiary amine reacts with hydrogen peroxide to form a tertiary amine oxide. The nitrogen atom in the amine oxide has a positive charge, and the oxygen atom bonded to it has a negative charge.
Step 4: Apply heat to the amine oxide. Upon heating, the amine oxide undergoes a Cope elimination reaction. This reaction involves the elimination of an alkyl group adjacent to the nitrogen atom, forming an alkene and a hydroxylamine.
Step 5: Determine the final products. The Cope elimination results in the formation of two products: an alkene (from the eliminated alkyl group) and a hydroxylamine. Analyze the structure to identify the specific alkene formed based on the alkyl groups attached to the nitrogen.
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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 atoms. 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 various transformations, including oxidation and elimination, depending on the reagents and conditions used.
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Hydrogen Peroxide as an Oxidizing Agent
Hydrogen peroxide (H2O2) is a powerful oxidizing agent commonly used in organic chemistry. When tertiary amines react with hydrogen peroxide, they can be oxidized to form N-oxides or other products, depending on the reaction conditions. This oxidation can lead to the formation of reactive intermediates that may further participate in elimination reactions.
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Cope Elimination
Cope elimination is a specific type of elimination reaction that typically occurs with tertiary amines and involves the removal of a leaving group and a hydrogen atom from adjacent carbon atoms, resulting in the formation of an alkene. This reaction is often facilitated by heat and can lead to the formation of double bonds, which are important in the synthesis of various organic compounds.
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Related Practice
Textbook Question
Name the following:
c.
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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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