Textbook Question
Draw all possible resonance contributors for the two carbocations in the preceding reaction. Use the resonance contributors to explain why 1-naphthol is the major product of the 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 37
Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 37Chapter 11, Problem 37
How do the major products obtained from rearrangement of the following arene oxides differ?
Verified step by step guidance1
Step 1: Analyze the given arene oxides. The structures provided are two arene oxides with isotopic labels (H and D) on the hydroxyl group and adjacent carbon. These isotopic labels will influence the rearrangement products due to their positions.
Step 2: Understand the rearrangement mechanism. Arene oxides typically undergo rearrangement via a NIH shift, where the substituent (hydrogen or deuterium) migrates to the adjacent carbon during the formation of phenols.
Step 3: Predict the migration pattern. In the first structure, the hydrogen (H) is positioned on the carbon adjacent to the oxygen, while deuterium (D) is on the hydroxyl group. During rearrangement, the hydrogen is likely to migrate to the oxygen-bearing carbon. In the second structure, the positions of H and D are reversed, so the deuterium will migrate instead.
Step 4: Consider the stereochemical implications. The migration of H or D will result in phenols with different isotopic labeling patterns. The major products will differ based on which isotope (H or D) migrates during the rearrangement.
Step 5: Conclude the difference in products. The major products obtained from the rearrangement of the two arene oxides will differ in the placement of isotopic labels (H and D) on the phenol ring, reflecting the migration patterns during the NIH shift.
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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. They typically contain an epoxide structure, where an oxygen atom is incorporated into the aromatic ring. Understanding their formation and reactivity is crucial, as they can undergo various rearrangements leading to different products, depending on the substituents on the aromatic ring and the reaction conditions.
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Rearrangement Reactions
Rearrangement reactions involve the structural reorganization of a molecule to form a different isomer. In the context of arene oxides, these reactions can lead to the formation of different products through mechanisms such as migration of substituents or ring opening. The specific pathways taken during rearrangement can significantly influence the nature and distribution of the final products.
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Product Distribution
Product distribution refers to the relative amounts of different products formed in a chemical reaction. In the case of arene oxide rearrangements, factors such as sterics, electronics, and the stability of intermediates play a critical role in determining which products are favored. Analyzing product distribution helps chemists understand the underlying mechanisms and predict the outcomes of similar reactions.
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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
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.
a. What would be the major product if the NIH shift occurs? (Hint: A C—H bond is easier to break than a C—D bond.)
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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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