Textbook Question
If a quaternary ammonium ion can undergo an elimination reaction with a strong base, why can’t a protonated tertiary amine undergo the same reaction?
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Ch. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing 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. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 41d
Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 41dChapter 11, Problem 41d
Three arene oxides can be obtained from phenanthrene.
d. Which of the three phenanthrene oxides is most likely to be carcinogenic?
Verified step by step guidance1
Identify the structure of phenanthrene and locate the positions where epoxidation can occur to form arene oxides. Phenanthrene is a polycyclic aromatic hydrocarbon with three fused benzene rings.
Understand that arene oxides are formed by the addition of an oxygen atom across a double bond in the aromatic ring, creating an epoxide group. In phenanthrene, this can occur at different positions, leading to different arene oxides.
Consider the stability and reactivity of each arene oxide. The most stable arene oxide is typically less reactive, while less stable ones may be more reactive and potentially more harmful.
Evaluate the potential for each arene oxide to form a reactive intermediate that can interact with biological molecules, such as DNA. This interaction is often a key factor in carcinogenicity.
Determine which arene oxide is most likely to form a stable carbocation or other reactive species that can lead to DNA adduct formation, a common mechanism for carcinogenicity. This typically involves analyzing the electronic and steric effects at each epoxidation site.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Arene Oxides
Arene oxides are reactive intermediates formed from the oxidation of aromatic compounds, such as phenanthrene. They typically contain an epoxide functional group, which can undergo further reactions, including rearrangements and hydrolysis. Understanding the structure and reactivity of arene oxides is crucial for assessing their biological activity and potential toxicity.
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Carcinogenicity
Carcinogenicity refers to the ability of a substance to cause cancer in living tissue. This property is often linked to the formation of DNA adducts, where reactive metabolites bind to DNA, leading to mutations. Evaluating the carcinogenic potential of compounds, such as phenanthrene oxides, involves understanding their metabolic pathways and the stability of their reactive intermediates.
Phenanthrene Metabolism
The metabolism of phenanthrene involves its biotransformation into various metabolites, including arene oxides, through enzymatic processes primarily in the liver. Cytochrome P450 enzymes play a significant role in this conversion, and the resulting metabolites can exhibit different levels of toxicity and carcinogenicity. Knowledge of these metabolic pathways is essential for predicting the health risks associated with phenanthrene and its derivatives.
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Related Practice
Textbook Question
Three arene oxides can be obtained from phenanthrene.
a. Draw the structures of the three phenanthrene oxides.
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Textbook Question
What are the major products of the following reaction?
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Textbook Question
Explain why the two arene oxides in [PROBLEM 10-38] open in opposite directions.
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Textbook Question
Explain why the half-life (the time it takes for one-half of the compound to be metabolized) of Xylocaine is longer than that of Novocaine.
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Textbook Question
Three arene oxides can be obtained from phenanthrene.
c. If a phenanthrene oxide can lead to the formation of more than one phenol, which phenol will be obtained in greater yield?
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