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 32a,b
Bruice 8th EditionCh. 19 - More About Amines • Reactions of Heterocyclic CompoundsProblem 32a,bChapter 20, Problem 32a,b
What products are obtained when the following tertiary amines react with hydrogen peroxide followed by heat?
a. 
b. 
Verified step by step guidance1
Step 1: Recognize the reaction type. The reaction involves tertiary amines reacting with hydrogen peroxide followed by heat. This is known as the Cope elimination reaction, where tertiary amines are oxidized to amine oxides, which then undergo elimination to form alkenes.
Step 2: Analyze the structure of the first compound (a). The tertiary amine has the structure (CH3)2NCH2CH2CH3. Upon reaction with hydrogen peroxide, the nitrogen atom is oxidized to form an amine oxide. The heat then induces elimination, leading to the formation of an alkene.
Step 3: Predict the elimination product for compound (a). The elimination occurs via a syn-elimination mechanism, where the hydrogen atom on the β-carbon (adjacent to the nitrogen) and the leaving group (oxygen bonded to nitrogen) are removed. This results in the formation of an alkene between the α and β carbons.
Step 4: Analyze the structure of the second compound (b). The tertiary amine has the structure CH3NCH2CH2CH3 with a phenyl group attached to the nitrogen. Similar to compound (a), the nitrogen is oxidized to an amine oxide, and heat induces elimination to form an alkene.
Step 5: Predict the elimination product for compound (b). The elimination follows the same syn-elimination mechanism. The phenyl group remains intact, and the alkene forms between the α and β carbons adjacent to the nitrogen. The product will be a phenyl-substituted alkene.
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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 nucleophiles due to the lone pair of electrons on the nitrogen. Understanding their structure and reactivity is crucial for predicting the products of reactions, especially with 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. In the context of tertiary amines, it can lead to the formation of N-oxides, which are important intermediates in organic synthesis. Recognizing the role of hydrogen peroxide in these reactions is essential for predicting the outcome.
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Thermal Decomposition of N-Oxides
When N-oxides are subjected to heat, they can undergo thermal decomposition, leading to the formation of various products, including alkenes and other nitrogen-containing compounds. This process is significant in understanding the final products of the reaction between tertiary amines and hydrogen peroxide, as heat can drive the reaction towards specific pathways.
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Related Practice
Textbook Question
Name the following:
a.
b.
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Textbook Question
What products are obtained when the following tertiary amines react with hydrogen peroxide followed by heat?
d.
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Textbook Question
Name the following:
c.
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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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