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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6:25 minutes

Problem 85d

Textbook Question

For each compound, show the products obtained from ozonolysis, followed by treatment with dimethyl sulfide.
d.

Verified step by step guidance

Step 1: Identify the structure of the compound provided. The compound is a cyclic alkene with a double bond at the top of the ring and another double bond within the ring. This is a diene structure.

Step 2: Understand the ozonolysis reaction. Ozonolysis involves the cleavage of double bonds using ozone (O₃), followed by reductive workup with dimethyl sulfide (DMS). Each double bond is cleaved to form carbonyl compounds.

Step 3: Analyze the positions of the double bonds. The double bond at the top of the ring will be cleaved, and the double bond within the ring will also be cleaved. Each cleavage will result in the formation of carbonyl groups (aldehydes or ketones).

Step 4: Predict the products. For the top double bond, cleavage will yield two carbonyl compounds based on the substituents attached to the double bond. For the internal double bond, cleavage will yield two additional carbonyl compounds.

Step 5: Combine the results. After ozonolysis and treatment with dimethyl sulfide, the final products will be a combination of aldehydes and/or ketones depending on the structure of the original compound. Ensure to draw the products based on the positions of the cleaved double bonds.

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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 occurs in two steps: first, the alkene reacts with ozone to form a molozonide, which rearranges to form ozonide. The ozonide is then hydrolyzed or treated with a reducing agent to yield the final carbonyl products.

Dimethyl Sulfide (DMS) Treatment

Dimethyl sulfide (DMS) is often used as a reducing agent in organic reactions, particularly following ozonolysis. After ozonolysis, DMS can convert ozonides into more stable carbonyl compounds, such as aldehydes or ketones, by reducing the ozonide intermediates. This step is crucial for obtaining the desired products in a more manageable form.

Mechanism of Ozonolysis

The mechanism of ozonolysis involves the formation of a cyclic molozonide intermediate, which is highly unstable and rearranges to form a more stable ozonide. This ozonide can then undergo cleavage to yield carbonyl compounds. Understanding this mechanism is essential for predicting the products of ozonolysis and the subsequent reactions with DMS, as it determines the structure of the final products.

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For each compound, show the products obtained from ozonolysis, followed by treatment with dimethyl sulfide. d.

Key Concepts

Ozonolysis

Dimethyl Sulfide (DMS) Treatment

Mechanism of Ozonolysis

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For each compound, show the products obtained from ozonolysis, followed by treatment with dimethyl sulfide.
d.