Textbook Question
What is the major product(s) of each of the following reactions?
d.
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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 63h
Bruice 8th EditionCh. 10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 63hChapter 11, Problem 63h
What is the major product(s) of each of the following reactions?
h. 
Verified step by step guidance1
Step 1: Identify the type of reaction. The reagents NaOCl (sodium hypochlorite) in CH3COOH (acetic acid) at 0°C indicate an oxidation reaction. Specifically, this is a hypochlorite oxidation, which is commonly used to convert secondary alcohols into ketones.
Step 2: Analyze the structure of the starting material. The molecule contains a secondary alcohol group (-OH) attached to a cyclopentane ring with an isopropyl substituent.
Step 3: Predict the site of oxidation. Secondary alcohols are oxidized to ketones. The hydroxyl group (-OH) will lose two hydrogen atoms: one from the oxygen and one from the carbon it is attached to, forming a carbonyl group (C=O).
Step 4: Consider the stereochemistry and regioselectivity. Since the reaction involves oxidation of the secondary alcohol, the product will retain the same carbon skeleton and substituents as the starting material, but the hydroxyl group will be replaced by a ketone group.
Step 5: Write the structure of the major product. The major product will be a cyclopentane ring with an isopropyl substituent and a ketone group at the position where the secondary alcohol was originally located.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Oxidation of Alcohols
Alcohols can undergo oxidation reactions, where they are converted into carbonyl compounds such as aldehydes or ketones. The oxidizing agent, in this case, sodium hypochlorite (NaOCl), facilitates this transformation. The reaction conditions, including temperature and solvent, can influence the product formed, with primary alcohols typically yielding aldehydes and secondary alcohols yielding ketones.
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Mechanism of Reaction
Understanding the mechanism of the oxidation reaction is crucial for predicting the major product. The reaction typically involves the formation of a chlorinated intermediate, followed by the loss of a water molecule, leading to the formation of the carbonyl compound. The specific pathway taken can depend on the structure of the alcohol and the reaction conditions.
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Role of Solvent
The choice of solvent can significantly affect the outcome of a chemical reaction. In this case, acetic acid (CH3COOH) serves as a solvent that can stabilize intermediates and influence the reactivity of the oxidizing agent. The solvent can also participate in the reaction, potentially leading to different products based on its properties, such as polarity and acidity.
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Related Practice
Textbook Question
Explain why the acid-catalyzed dehydration of an alcohol is a reversible reaction, whereas the base-promoted dehydrohalogenation of an alkyl halide is an irreversible reaction.
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Textbook Question
In Section 10.12, we saw that S-adenosylmethionine (SAM) methylates the nitrogen atom of noradrenaline to form adrenaline, a more potent hormone. If SAM methylates an OH group attached to the benzene ring instead, it completely destroys noradrenaline's activity.
b. Which reaction is more apt to occur, methylation on nitrogen or methylation on oxygen?
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Textbook Question
What is the major product(s) of each of the following reactions?
g.
Textbook Question
An unknown alcohol with a molecular formula of C7H14O was oxidized to an aldehyde with HOCl. When an acidic solution of the alcohol was distilled, two alkenes were obtained. The alkene formed in greater yield was determined to be 1-methylcyclohexene. The other alkene formed the original un-known alcohol when treated with BH3/THF followed by H2O2, HO-, and H2O. Identify the unknown alcohol.
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Textbook Question
What is the major product(s) of each of the following reactions?
c.
1
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