Textbook Question
What alkene gives the product shown after reaction first with ozone and then with dimethyl sulfide?
b.
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10. Addition Reactions
Ozonolysis
2:57 minutesProblem 103b
Textbook Question
Ozonolysis of an alkene, followed by treatment with dimethyl sulfide, forms the following product(s). Identify the alkene in each case.
b. 
Verified step by step guidance1
Step 1: Understand the reaction. Ozonolysis is a reaction where an alkene reacts with ozone (O₃) to form an ozonide intermediate. This intermediate is then reduced using a reducing agent, such as dimethyl sulfide (DMS), to yield carbonyl compounds (aldehydes or ketones).
Step 2: Analyze the given product(s). Identify the carbonyl compounds (aldehydes or ketones) formed after the ozonolysis and reduction steps. These products will help you deduce the structure of the original alkene.
Step 3: Reconstruct the alkene. Combine the carbonyl compounds by 'reversing' the cleavage process. Connect the carbon atoms of the carbonyl groups at the positions where the double bond was originally present in the alkene.
Step 4: Ensure the correct structure. Verify that the reconstructed alkene has the correct number of carbons and matches the connectivity implied by the carbonyl products. Also, ensure that the stereochemistry (if applicable) is consistent with the reaction conditions.
Step 5: Confirm the answer. Double-check the reaction mechanism to ensure that the proposed alkene would indeed produce the given carbonyl products upon ozonolysis followed by reduction with dimethyl sulfide.
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Video duration:
2mKey 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 ozonides, which can then be further reduced. This reaction typically results in the formation of carbonyl compounds, such as aldehydes or ketones, depending on the structure of the alkene. Understanding ozonolysis is crucial for predicting the products formed from specific alkenes.
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General properties of ozonolysis.
Dimethyl Sulfide (DMS) Reduction
Dimethyl sulfide (DMS) is commonly used as a reducing agent in organic chemistry, particularly in the reduction of ozonides formed during ozonolysis. The treatment of ozonides with DMS converts them into more stable carbonyl compounds, allowing for the identification of the original alkene. Recognizing the role of DMS is essential for understanding the final products of ozonolysis.
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Alkene Structure and Reactivity
The structure of alkenes, characterized by a carbon-carbon double bond, significantly influences their reactivity in reactions like ozonolysis. Factors such as substitution patterns (e.g., whether the alkene is terminal or internal) affect the products formed during ozonolysis. A solid grasp of alkene structures is necessary to deduce the original alkene from the products generated in the reaction.
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