Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

10. Addition Reactions

Ozonolysis

Organic Chemistry

10. Addition Reactions

Ozonolysis

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6:18 minutes

Problem 34c

Textbook Question

The following product was obtained from the ozonolysis of an alkene followed by treatment with dimethyl sulfide. What is the structure of the alkene?
c.

Verified step by step guidance

Analyze the product structure obtained from ozonolysis. The image shows a cyclic compound with two carbonyl groups (C=O) located on opposite ends of the ring. This indicates that the original alkene was cleaved at the double bond, forming two carbonyl groups.

Recall the mechanism of ozonolysis. Ozone (O₃) reacts with an alkene to form an ozonide intermediate, which is then reduced by dimethyl sulfide (DMS) to yield aldehydes or ketones. In this case, the product contains two ketones, suggesting the original alkene was symmetrical.

Determine the structure of the original alkene. Since the product is a cyclic compound with two ketones on opposite ends, the original alkene must have been a cyclic compound with a double bond connecting the two carbons that now bear the ketones.

Consider the ring size and connectivity. The product is an 8-membered ring, so the original alkene must also have been an 8-membered ring with a double bond positioned symmetrically to yield the observed ketones upon cleavage.

Draw the structure of the original alkene. The double bond should be placed between the two carbons that correspond to the positions of the ketones in the product. This ensures that ozonolysis followed by reduction with DMS produces the observed product.

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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 cyclic ozonide intermediate, which is then reduced to yield the final products. Understanding ozonolysis is crucial for determining the structure of the original alkene based on the products formed.

Dimethyl Sulfide (DMS) Reduction

Dimethyl sulfide (DMS) is commonly used as a reducing agent in organic chemistry, particularly in the context of ozonolysis. After the formation of ozonides, DMS can reduce these intermediates to yield carbonyl compounds. Recognizing the role of DMS in the reaction helps in predicting the final structure of the products and, consequently, the original alkene structure.

Alkene Structure and Reactivity

The structure of alkenes, characterized by a carbon-carbon double bond, significantly influences their reactivity in various chemical reactions, including ozonolysis. The position and substitution of the double bond determine the products formed during ozonolysis. A solid grasp of alkene structures, including stereochemistry and functional groups, is essential for deducing the original alkene from the ozonolysis products.

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The following product was obtained from the ozonolysis of an alkene followed by treatment with dimethyl sulfide. What is the structure of the alkene?c.

Key Concepts

Ozonolysis

Dimethyl Sulfide (DMS) Reduction

Alkene Structure and Reactivity

Watch next

The following product was obtained from the ozonolysis of an alkene followed by treatment with dimethyl sulfide. What is the structure of the alkene?
c.