Textbook Question
Draw the product(s) you'd expect when each of these alkenes is treated first with O3, then with CH3SCH3
(c)
10. Addition Reactions
Ozonolysis
4:04 minutesProblem 85e
Textbook Question
For each compound, show the products obtained from ozonolysis, followed by treatment with dimethyl sulfide.
e. 
Verified step by step guidance1
Step 1: Identify the double bonds in the given compound. In the provided structure, there are two double bonds: one within the ring and one outside the ring.
Step 2: Understand the ozonolysis reaction. Ozonolysis involves the cleavage of double bonds by ozone (O₃), forming ozonides as intermediates. These ozonides are then reduced to carbonyl compounds (aldehydes or ketones) using a reducing agent such as dimethyl sulfide (DMS).
Step 3: Break each double bond symmetrically. For the double bond within the ring, split it into two carbonyl groups. For the double bond outside the ring, split it into two carbonyl groups as well. Each carbon involved in the double bond will form a carbonyl group (C=O).
Step 4: Assign the products based on the cleavage. For the double bond within the ring, the two carbons will form ketones or aldehydes depending on their substituents. For the double bond outside the ring, the two carbons will form aldehydes or ketones as well.
Step 5: Draw the final products. After ozonolysis and treatment with dimethyl sulfide, the compound will yield specific carbonyl compounds. Ensure that the products are consistent with the positions of the original double bonds in the structure.
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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, typically aldehydes or ketones. The reaction proceeds through the formation of a cyclic ozonide intermediate, which is then hydrolyzed to yield the final carbonyl products. Understanding the structure of the starting alkene is crucial, as it determines the nature and position of the resulting carbonyl groups.
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Dimethyl Sulfide (DMS) Treatment
After ozonolysis, the treatment with dimethyl sulfide (DMS) serves to reduce the ozonide intermediate, converting it into stable carbonyl compounds. DMS acts as a nucleophile, attacking the electrophilic carbon of the ozonide, which helps in the stabilization of the products. This step is essential for completing the reaction sequence and obtaining the final products in a more manageable form.
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Product Identification
Identifying the products of ozonolysis followed by DMS treatment requires a solid understanding of the starting material's structure and the reaction mechanisms involved. The products can vary significantly based on the substitution pattern of the alkene, leading to different aldehydes or ketones. Familiarity with functional group transformations and the ability to predict the outcomes based on the reaction conditions is vital for accurately determining the final products.
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