Textbook Question
Give the products expected when the following tertiary amines are treated with a peroxyacid and heated.
(b) N,N-diethylhexan-2-amine
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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 21c
Give the products expected when the following tertiary amines are treated with a peroxyacid and heated.
(c) cyclohexyldimethylamine
Verified step by step guidance1
Understand the reaction: The reaction involves the oxidation of a tertiary amine using a peroxyacid. This process is known as the Cope elimination, where the tertiary amine is converted into an N-oxide intermediate, which then undergoes elimination upon heating to form an alkene.
Step 1: Identify the structure of the given tertiary amine. Cyclohexyldimethylamine consists of a cyclohexyl group attached to a nitrogen atom, which is also bonded to two methyl groups.
Step 2: React the tertiary amine with a peroxyacid (e.g., m-chloroperoxybenzoic acid, MCPBA). The peroxyacid oxidizes the nitrogen atom of the tertiary amine to form an N-oxide. The structure of the N-oxide will have a cyclohexyl group, two methyl groups, and an oxygen atom bonded to the nitrogen.
Step 3: Heat the N-oxide intermediate. Heating induces the Cope elimination, where the N-oxide undergoes a concerted elimination reaction. A hydrogen atom from the β-carbon (relative to the nitrogen) and the N-oxide group are eliminated, forming a double bond in the process.
Step 4: Determine the product. The elimination will result in the formation of an alkene. In this case, the product will be cyclohexene, as the β-hydrogen is removed from the cyclohexyl group, leading to the formation of a double bond in the cyclohexane ring.
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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 oxidation, which is relevant when treated with peroxyacids, leading to the formation of N-oxides.
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Naming Secondary and Tertiary Amines
Peroxyacids
Peroxyacids, also known as peracids, are organic compounds that contain a peroxy group (-O-O-) bonded to a carbon atom. They are strong oxidizing agents and can react with various substrates, including amines, to introduce oxygen functionalities. When tertiary amines react with peroxyacids, they can form N-oxides, which are important intermediates in organic synthesis.
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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 leads to 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 like peroxyacids.
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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
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.
(b) Some Zaitsev product is also formed. It has the (E) configuration. When the same amine is treated with mCPBA and heated, the Zaitsev product has the (Z) configuration. Use stereochemical drawings of the transition states to explain these observations.
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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
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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