Textbook Question
Identify each of the following reactions as an oxidation reaction, a reduction reaction, or neither.
a.
b.
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Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions
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. 6 - The Reactions of Alkenes • The Stereochemistry of Addition ReactionsProblem 30b
Bruice 8th EditionCh. 6 - The Reactions of Alkenes • The Stereochemistry of Addition ReactionsProblem 30bChapter 7, Problem 30b
What products are formed when the following compounds react with ozone and then with dimethyl sulfide?
b. 
Verified step by step guidance1
Step 1: Recognize the reaction type. The problem involves ozonolysis, a reaction where ozone (O₃) cleaves double bonds in alkenes to form carbonyl compounds. The second step involves treatment with dimethyl sulfide (DMS), which reduces the ozonide intermediate to aldehydes or ketones.
Step 2: Analyze the structure of the given compound. The compound contains a cyclohexane ring with a double bond attached to a methyl group. The double bond is the reactive site for ozonolysis.
Step 3: Predict the cleavage of the double bond. Ozone will cleave the double bond into two fragments. Each carbon involved in the double bond will form a carbonyl group (either an aldehyde or ketone).
Step 4: Consider the role of dimethyl sulfide (DMS). DMS reduces the ozonide intermediate formed during ozonolysis into stable carbonyl compounds. This ensures that the products are aldehydes or ketones rather than carboxylic acids.
Step 5: Identify the products. The cleavage of the double bond will yield two carbonyl compounds: one from the methyl group side (a formaldehyde molecule) and one from the cyclohexane ring side (a ketone with the cyclohexane ring attached).
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Ozonolysis
Ozonolysis is a reaction involving the cleavage of alkenes or alkynes using ozone (O3) to form carbonyl compounds, such as aldehydes and ketones. The reaction typically proceeds through the formation of a molozonide intermediate, which rearranges to yield ozonides. This process is crucial for determining the structure of organic compounds and is often followed by reductive workup, commonly using dimethyl sulfide (DMS) to convert ozonides into stable products.
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General properties of ozonolysis.
Dimethyl Sulfide (DMS) as a Reductant
Dimethyl sulfide (DMS) is frequently used as a reducing agent in organic chemistry, particularly in the reductive workup of ozonolysis reactions. It effectively reduces ozonides to aldehydes or ketones, facilitating the formation of stable products. DMS is favored for its mild reaction conditions and ability to selectively reduce ozonides without further oxidation of the carbonyl products.
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Reaction Mechanism
Understanding the reaction mechanism of ozonolysis is essential for predicting the products formed. The mechanism involves the initial formation of a cyclic molozonide, which then rearranges to form a more stable ozonide. The subsequent reaction with DMS leads to the cleavage of the ozonide, resulting in the formation of carbonyl compounds. Familiarity with these steps allows chemists to anticipate the outcome of reactions involving ozone and various organic substrates.
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Related Practice
Textbook Question
What alkene would you treat with a peroxyacid in order to obtain each of the epoxides in Problem 27?
c. 2,2,3,3-tetramethyloxirane
d. 2,3-epoxy-2-methylpentane
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Textbook Question
What products are formed when the following compounds react with ozone and then with dimethyl sulfide?
c.
d.
1
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Textbook Question
What products are formed when the following compounds react with ozone and then with dimethyl sulfide?
a.
1
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Textbook Question
What alkene would give only a ketone with three carbons as a product of oxidative cleavage?
Textbook Question
What products are formed when the following compounds react with ozone and then with dimethyl sulfide?
e.
f.
2
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