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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5:47 minutes

Problem 94b

Textbook Question

What alkene gives the product shown after reaction first with ozone and then with dimethyl sulfide?
b.

Verified step by step guidance

Step 1: Understand the reaction mechanism. Ozonolysis is a reaction where an alkene reacts with ozone (O₃) to form an ozonide intermediate. This intermediate is then reduced by dimethyl sulfide (DMS) to yield carbonyl compounds (aldehydes or ketones). The product structure provided shows two ketones, indicating the cleavage of a double bond in the original alkene.

Step 2: Analyze the product structure. The product contains two ketones: one is part of a cyclohexanone ring, and the other is a ketone group attached to a cyclopentane ring. This suggests that the original alkene was part of a cyclic structure that was cleaved into these two fragments.

Step 3: Reconstruct the original alkene. To determine the alkene, reverse the ozonolysis process. Connect the two carbonyl carbons in the product structure with a double bond. This double bond represents the original alkene that underwent ozonolysis.

Step 4: Verify the connectivity. Ensure that the reconstructed alkene matches the product after ozonolysis and reduction. The double bond should be positioned such that cleavage yields the observed ketones.

Step 5: Draw the original alkene. Based on the analysis, the original alkene is a cyclic structure with a double bond connecting the two carbonyl carbons. This alkene would yield the given product after ozonolysis followed by reduction with dimethyl sulfide.

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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. The process typically occurs in two steps: first, the alkene reacts with ozone to form a molozonide, which rearranges to form ozonide. This ozonide is then reduced, often using a reagent like dimethyl sulfide (DMS), to yield aldehydes or ketones, depending on the structure of the original alkene.

Dimethyl Sulfide (DMS)

Dimethyl sulfide is a common reducing agent used in organic chemistry, particularly in the reduction of ozonides formed during ozonolysis. DMS effectively converts the ozonide into stable carbonyl compounds, such as aldehydes or ketones, by donating electrons and facilitating the removal of the ozone-derived functional groups. Its use is favored due to its mildness and ability to produce fewer side products.

Alkene Structure and Reactivity

The structure of alkenes, characterized by a carbon-carbon double bond, significantly influences their reactivity in chemical reactions. The position and substitution of the double bond determine how the alkene will react with ozone and other reagents. Understanding the stereochemistry and the electronic effects of substituents on the alkene is crucial for predicting the products of ozonolysis and other reactions.

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What alkene gives the product shown after reaction first with ozone and then with dimethyl sulfide? b.

Key Concepts

Ozonolysis

Dimethyl Sulfide (DMS)

Alkene Structure and Reactivity

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What alkene gives the product shown after reaction first with ozone and then with dimethyl sulfide?
b.