Textbook Question
Give the products expected when the following tertiary amines are treated with a peroxyacid and heated.
(c) cyclohexyldimethylamine
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Ch. 19 - Amines
Wade9th EditionOrganic ChemistryISBN: 9780135213728
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Table of contents
- Ch.1 - Structure and Bonding107
- Ch. 2 - Acids and Bases; Functional Groups115
- Ch.3 - Structure and Stereochemistry of Alkanes100
- Ch.4 - The Study of Chemical Reactions99
- Ch.5 - Stereochemistry93
- Ch.6 - Alkyl Halides; Nucleophilic Substitution118
- Ch. 7 - Structure and Synthesis of Alkenes; Elimination158
- Ch.8 - Reactions of Alkenes171
- Ch.9 - Alkynes91
- Ch.10 - Structure and Synthesis of Alcohols143
- Ch.11 - Reactions of Alcohols104
- Ch. 12 - Infrared Spectroscopy and Mass Spectrometry22
- Ch. 13 - Nuclear Magnetic Resonance Spectroscopy45
- Ch. 14 - Ethers, Epoxides, and Thioethers72
- Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy89
- Ch. 16 - Aromatic Compounds74
- Ch. 17 - Reactions of Aromatic Compounds126
- Ch. 18 - Ketones and Aldehydes193
- Ch. 19 - Amines129
- Ch. 20 - Carboxylic Acids77
- Ch. 21 - Carboxylic Acid Derivatives141
- Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds175
- Ch. 23 - Carbohydrates and Nucleic Acids93
- Ch. 24 - Amino Acids, Peptides, and Proteins54
Chapter 19, Problem 21b
Give the products expected when the following tertiary amines are treated with a peroxyacid and heated.
(b) N,N-diethylhexan-2-amine
Verified step by step guidance1
Identify the reaction type: The reaction involves a tertiary amine being treated with a peroxyacid. This is a Cope elimination reaction, where the tertiary amine is oxidized to an amine oxide, followed by elimination to form an alkene.
Oxidation step: The tertiary amine, N,N-diethylhexan-2-amine, reacts with the peroxyacid to form the corresponding amine oxide. The structure of the amine oxide will have an oxygen atom bonded to the nitrogen atom, creating a positively charged nitrogen and a negatively charged oxygen.
Analyze the structure of the amine oxide: The amine oxide will have a β-hydrogen (a hydrogen atom on the carbon adjacent to the carbon bonded to the nitrogen). This β-hydrogen is crucial for the elimination step.
Elimination step: Upon heating, the amine oxide undergoes a syn-elimination (both the β-hydrogen and the leaving group are eliminated from the same side of the molecule). This results in the formation of an alkene. Identify the β-hydrogens in the structure and determine the possible alkenes that can form.
Determine the major product: Based on Zaitsev's rule, the more substituted alkene is typically the major product. Analyze the possible alkenes formed and identify the one with the highest degree of substitution as the major product.
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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 nucleophiles due to the lone pair of electrons on the nitrogen. In reactions, tertiary amines can undergo various transformations, including oxidation, which is relevant when treated with peroxyacids.
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Naming Secondary and Tertiary Amines
Peroxyacids
Peroxyacids are organic compounds that contain a peroxy group (-O-O-) bonded to a carbon atom. They are strong oxidizing agents and can facilitate the oxidation of amines to form N-oxides. When tertiary amines react with peroxyacids, they can lead to the formation of N-oxide products, which are important in various organic synthesis processes.
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Oxidation Reactions
Oxidation reactions involve the loss of electrons or an increase in oxidation state by a molecule. In the context of tertiary amines and peroxyacids, the oxidation process typically results in the formation of N-oxides. Understanding the mechanism of these reactions is crucial for predicting the products formed when tertiary amines are treated with oxidizing agents.
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Related Practice
Textbook Question
Give the products expected when the following tertiary amines are treated with a peroxyacid and heated.
(a) N,N-dimethylhexan-2-amine
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Textbook Question
Give the products expected when the following tertiary amines are treated with a peroxyacid and heated.
(d) N-ethylpiperidine
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Textbook Question
Predict the major products formed when the following amines undergo exhaustive methylation, treatment with Ag2O, and heating.
(e)
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Textbook Question
Predict the major products formed when the following amines undergo exhaustive methylation, treatment with Ag2O, and heating.
(a) hexan-2-amine
(b) 2-methylpiperidine
(c) N-ethylpiperidine
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Textbook Question
When the (R,R) isomer of the amine shown is treated with an excess of methyl iodide, then silver oxide, then heated, the major product is the Hofmann product.
(a) Draw the structure of the major (Hofmann) product.
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