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 41c
Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 41cChapter 11, Problem 41c
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?
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 epoxidation of the double bonds in the aromatic rings. In phenanthrene, the most reactive positions for epoxidation are typically at the 9,10 positions due to the higher electron density.
Consider the mechanism of arene oxide rearrangement to phenols. Arene oxides can undergo a rearrangement via a 1,2-hydride or 1,2-alkyl shift, leading to the formation of phenols.
Analyze the stability of the possible phenols formed from the rearrangement. The phenol that is more stable due to resonance or steric factors will generally be formed in greater yield.
Evaluate the regioselectivity of the rearrangement process. The phenol formed in greater yield will likely be the one where the rearrangement leads to a more stable carbocation intermediate, facilitating the shift and subsequent formation of the phenol.
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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 are characterized by an epoxide structure, where an oxygen atom is incorporated into the aromatic ring, creating a three-membered cyclic ether. Understanding the formation and reactivity of arene oxides is crucial for predicting the products of subsequent reactions, including the formation of phenols.
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Phenol Formation
Phenols are organic compounds containing a hydroxyl (-OH) group attached to an aromatic ring. The formation of phenols from arene oxides typically involves nucleophilic attack by water or other nucleophiles, leading to ring-opening and rearrangement. The specific conditions and substituents on the aromatic ring can influence which phenol is produced and in what yield, making it essential to analyze the reaction pathways.
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Reaction Mechanisms
Understanding reaction mechanisms is vital in organic chemistry as it explains the step-by-step process by which reactants transform into products. In the context of phenanthrene oxides, the mechanism will detail how the arene oxide can lead to different phenols, including factors that affect the yield of each phenol. Knowledge of mechanisms helps predict the most favorable pathways and the stability of intermediates, guiding the expected outcomes of the reaction.
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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
Explain why the two arene oxides in [PROBLEM 10-38] open in opposite directions.
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Textbook Question
Three arene oxides can be obtained from phenanthrene.
d. Which of the three phenanthrene oxides is most likely to be carcinogenic?
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Textbook Question
How do the major products obtained from rearrangement of the following arene oxides differ?
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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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