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 21d
Give the products expected when the following tertiary amines are treated with a peroxyacid and heated.
(d) N-ethylpiperidine
Verified step by step guidance1
Identify the reaction type: The reaction involves a tertiary amine (N-ethylpiperidine) being treated with a peroxyacid. This is a Cope elimination reaction, which occurs when an amine oxide undergoes thermal decomposition to form an alkene and a hydroxylamine.
Oxidation of the tertiary amine: Treat the tertiary amine (N-ethylpiperidine) with a peroxyacid (e.g., mCPBA). This step oxidizes the nitrogen atom in the amine to form an amine oxide. The structure of the amine oxide will have 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 nitrogen). This β-hydrogen is crucial for the elimination step.
Perform the Cope elimination: Upon heating, the amine oxide undergoes a concerted elimination reaction. The β-hydrogen is removed, and a double bond forms between the α- and β-carbons, while the nitrogen-oxygen bond breaks to form a hydroxylamine.
Determine the final products: The products of the reaction will be an alkene (formed by the elimination) and a hydroxylamine (derived from the amine oxide). For N-ethylpiperidine, the alkene will be a cyclic compound with a double bond in the piperidine ring, and the hydroxylamine will retain the ethyl group.
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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 and acylation, which are relevant when discussing their behavior with peroxyacids.
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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 amines to form N-oxides or other oxidized products. Understanding the reactivity of peroxyacids is crucial for predicting the products formed when they interact with tertiary amines like N-ethylpiperidine.
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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 reacting with peroxyacids, oxidation can lead to the formation of N-oxides, which are stable products resulting from the addition of an oxygen atom to the nitrogen. Recognizing the nature of these reactions helps in predicting the expected products when heating tertiary amines with 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.
(c) cyclohexyldimethylamine
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Textbook Question
Predict the products from the reactions of the following amines with sodium nitrite in dilute HCl.
(b) N-ethylhexan-2-amine
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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
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
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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