Textbook Question
Explain why the two arene oxides in [PROBLEM 10-38] open in opposite directions.
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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 41a
Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 41aChapter 11, Problem 41a
Three arene oxides can be obtained from phenanthrene.
a. Draw the structures of the three phenanthrene oxides.
Verified step by step guidance1
Step 1: Phenanthrene is a polycyclic aromatic hydrocarbon composed of three fused benzene rings. To form arene oxides, an epoxide group (-O-) is introduced into one of the double bonds in the aromatic rings.
Step 2: Identify the three double bonds in phenanthrene that can undergo epoxidation. These are located in the central ring and the two outer rings. Each double bond can form an arene oxide.
Step 3: Draw the first phenanthrene oxide by epoxidizing the double bond in the central ring. This involves adding an oxygen atom to form a three-membered epoxide ring.
Step 4: Draw the second phenanthrene oxide by epoxidizing one of the double bonds in the left outer ring. Again, add an oxygen atom to form a three-membered epoxide ring.
Step 5: Draw the third phenanthrene oxide by epoxidizing one of the double bonds in the right outer ring. Add an oxygen atom to form a three-membered epoxide ring.
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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, where an oxygen atom is incorporated into a three-membered ring structure. Understanding the formation and reactivity of arene oxides is crucial for predicting the products of reactions involving aromatic compounds.
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Phenanthrene Structure
Phenanthrene is a polycyclic aromatic hydrocarbon consisting of three fused benzene rings. Its structure is essential for understanding how different oxidation positions can lead to the formation of various arene oxides. The specific arrangement of carbon atoms in phenanthrene influences the stability and reactivity of the resulting oxides.
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Epoxidation Reaction
Epoxidation is a chemical reaction that converts alkenes or aromatic compounds into epoxides, which are cyclic ethers with a three-membered ring. In the context of phenanthrene, epoxidation can occur at different positions on the aromatic rings, leading to the formation of distinct arene oxides. Familiarity with the mechanisms and regioselectivity of epoxidation is vital for accurately drawing the structures of the phenanthrene oxides.
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Related Practice
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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Textbook Question
The existence of the NIH shift was established by determining the major product obtained from rearrangement of the following arene oxide, in which a hydrogen has been replaced by a deuterium.
b. What would be the major product if the carbocation forms phenol by losing H+ or D+, rather than by going through the NIH shift?
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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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