Textbook Question
For each compound, show the products obtained from ozonolysis, followed by treatment with dimethyl sulfide.
c.
3
views
Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions
Bruice8th EditionOrganic ChemistryISBN: 9780135213711
Not the one you use?Change textbookSelect a different textbook
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
All textbooks
Bruice 8th EditionCh. 6 - The Reactions of Alkenes • The Stereochemistry of Addition ReactionsProblem 85d
Bruice 8th EditionCh. 6 - The Reactions of Alkenes • The Stereochemistry of Addition ReactionsProblem 85dChapter 7, Problem 85d
For each compound, show the products obtained from ozonolysis, followed by treatment with dimethyl sulfide.
d. 
Verified step by step guidance1
Step 1: Identify the structure of the compound provided. The compound is a cyclic alkene with a double bond at the top of the ring and another double bond within the ring. This is a diene structure.
Step 2: Understand the ozonolysis reaction. Ozonolysis involves the cleavage of double bonds using ozone (O₃), followed by reductive workup with dimethyl sulfide (DMS). Each double bond is cleaved to form carbonyl compounds.
Step 3: Analyze the positions of the double bonds. The double bond at the top of the ring will be cleaved, and the double bond within the ring will also be cleaved. Each cleavage will result in the formation of carbonyl groups (aldehydes or ketones).
Step 4: Predict the products. For the top double bond, cleavage will yield two carbonyl compounds based on the substituents attached to the double bond. For the internal double bond, cleavage will yield two additional carbonyl compounds.
Step 5: Combine the results. After ozonolysis and treatment with dimethyl sulfide, the final products will be a combination of aldehydes and/or ketones depending on the structure of the original compound. Ensure to draw the products based on the positions of the cleaved double bonds.
Verified video answer for a similar problem:
This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
6mWas this helpful?
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 occurs in two steps: first, the alkene reacts with ozone to form a molozonide, which rearranges to form ozonide. The ozonide is then hydrolyzed or treated with a reducing agent to yield the final carbonyl products.
Recommended video:
Guided course
06:30
General properties of ozonolysis.
Dimethyl Sulfide (DMS) Treatment
Dimethyl sulfide (DMS) is often used as a reducing agent in organic reactions, particularly following ozonolysis. After ozonolysis, DMS can convert ozonides into more stable carbonyl compounds, such as aldehydes or ketones, by reducing the ozonide intermediates. This step is crucial for obtaining the desired products in a more manageable form.
Recommended video:
Guided course
03:51Reagents used to oxidize Sulfides.
Mechanism of Ozonolysis
The mechanism of ozonolysis involves the formation of a cyclic molozonide intermediate, which is highly unstable and rearranges to form a more stable ozonide. This ozonide can then undergo cleavage to yield carbonyl compounds. Understanding this mechanism is essential for predicting the products of ozonolysis and the subsequent reactions with DMS, as it determines the structure of the final products.
Recommended video:
Guided course
06:30General properties of ozonolysis.
Related Practice
Textbook Question
For each compound, show the products obtained from ozonolysis, followed by treatment with dimethyl sulfide.
e.
1
views
Textbook Question
For each compound, show the products obtained from ozonolysis, followed by treatment with dimethyl sulfide.
a.
2
views
Textbook Question
Which stereoisomer of 3,4-dimethyl-3-hexene forms (3S,4S)-3,4-dimethylhexane and (3R,4R)-3,4-dimethylhexane when it reacts with H2, Pd/C?
2
views
Textbook Question
Draw the products of the following reactions. If the products can exist as stereoisomers show what stereoisomers are formed.
g. 3,3-dimethyl-1-pentene + HBr
2
views
Textbook Question
For each compound, show the products obtained from ozonolysis, followed by treatment with dimethyl sulfide.
b.
1
views