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 20e
Predict the major products formed when the following amines undergo exhaustive methylation, treatment with Ag2O, and heating.
(e) 
Verified step by step guidance1
Step 1: Identify the starting material. The given compound is a secondary amine with a bicyclic structure containing a nitrogen atom. The nitrogen is bonded to one hydrogen atom and part of the bicyclic ring system.
Step 2: Understand the reaction sequence. Exhaustive methylation involves treating the amine with excess methyl iodide (CH3I), which converts the amine into a quaternary ammonium salt. The nitrogen atom will be fully methylated, forming a positively charged quaternary ammonium ion.
Step 3: Treatment with Ag2O. Silver oxide (Ag2O) is used to replace the iodide ion in the quaternary ammonium salt with a hydroxide ion, forming a quaternary ammonium hydroxide. This step prepares the compound for elimination.
Step 4: Heating the quaternary ammonium hydroxide. Upon heating, the hydroxide ion acts as a base, facilitating an elimination reaction (Hofmann elimination). This results in the formation of an alkene. The elimination typically follows the Hofmann rule, favoring the formation of the less substituted alkene.
Step 5: Predict the major product. Analyze the bicyclic structure to determine the possible positions for double bond formation. The major product will be the less substituted alkene formed via elimination, considering steric and electronic factors in the bicyclic system.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Exhaustive Methylation
Exhaustive methylation is a chemical process where amines are treated with methylating agents, such as methyl iodide, to convert them into quaternary ammonium salts. This reaction typically involves the complete substitution of hydrogen atoms in the amine with methyl groups, leading to the formation of a stable quaternary ammonium compound. Understanding this process is crucial for predicting the products of amines when subjected to methylation.
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Provide the Major Product
Ag2O Treatment
Silver oxide (Ag2O) is often used in organic chemistry to facilitate the oxidation of amines. When quaternary ammonium salts are treated with Ag2O, they can undergo dealkylation, where one or more alkyl groups are removed, leading to the formation of amines and other products. This step is essential for understanding how the structure of the initial amine changes during the reaction sequence.
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Heating in Organic Reactions
Heating is a common technique in organic chemistry that can drive reactions to completion or promote rearrangements. In the context of amines and their derivatives, heating can facilitate the elimination of small molecules, such as methyl groups, and promote the formation of more stable products. Recognizing the role of heat in these reactions is vital for predicting the final products formed after exhaustive methylation and Ag2O treatment.
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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
Give the products expected when the following tertiary amines are treated with a peroxyacid and heated.
(a) N,N-dimethylhexan-2-amine
Textbook Question
Show how you would use the same sulfonyl chloride as used in the sulfanilamide synthesis to make sulfathiazole and sulfapyridine.
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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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