Textbook Question
What are the products of the following reactions? Indicate whether each reaction is an oxidation or a reduction.
a.
10. Addition Reactions
Ozonolysis
1:23 minutesProblem 94c
Textbook Question
What alkene gives the product shown after reaction first with ozone and then with dimethyl sulfide?
c. 
Verified step by step guidance1
Step 1: Understand the reaction mechanism. Ozonolysis is a reaction where an alkene reacts with ozone (O₃) to form an ozonide intermediate, which is then reduced by a reducing agent such as dimethyl sulfide (DMS) to yield carbonyl compounds (aldehydes or ketones).
Step 2: Analyze the product structure. The image shows two aldehyde groups (H-C=O) attached to a cyclopentane ring. This indicates that the original alkene was cleaved at the double bond, forming these two aldehyde groups.
Step 3: Determine the location of the double bond in the original alkene. Since the product contains two aldehyde groups, the double bond in the original alkene must have been located between the two carbons that now bear the aldehyde groups.
Step 4: Reconstruct the original alkene. To form the observed product, the original alkene must have been cyclopentene, with the double bond located between the two carbons that were cleaved during ozonolysis.
Step 5: Verify the reasoning. When cyclopentene undergoes ozonolysis followed by reduction with dimethyl sulfide, the double bond is cleaved, and the two carbons involved in the double bond are converted into aldehyde groups, matching the product shown in the image.
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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 using ozone (O3) to form carbonyl compounds, such as aldehydes or ketones. The reaction typically proceeds through the formation of a cyclic ozonide intermediate, which is then reduced to yield the final products. Understanding this process is crucial for predicting the products formed from a given alkene.
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Dimethyl Sulfide (DMS) as a Reducing Agent
Dimethyl sulfide (DMS) is commonly used as a reducing agent in organic reactions, particularly in the workup of ozonolysis. After the formation of ozonides, DMS reduces these intermediates to yield stable carbonyl compounds. Recognizing the role of DMS helps in understanding how the final products are derived from the ozonolysis reaction.
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Alkene Structure and Reactivity
The structure of alkenes, characterized by a carbon-carbon double bond, significantly influences their reactivity in chemical reactions. Factors such as sterics, substitution patterns, and the presence of functional groups determine how alkenes will react with ozone and other reagents. A solid grasp of alkene structure is essential for predicting the outcomes of ozonolysis and subsequent reactions.
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