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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6:09 minutes

Problem 85c

Textbook Question

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

Verified step by step guidance

Step 1: Identify the double bonds in the compound. The given structure is a bicyclic compound with two double bonds: one in the six-membered ring and one exocyclic double bond.

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: Predict the cleavage products for the exocyclic double bond. The exocyclic double bond will split into two fragments: one fragment will be a ketone, and the other will be a formaldehyde molecule.

Step 4: Predict the cleavage products for the double bond in the ring. The double bond within the six-membered ring will split into two carbonyl compounds, likely two ketones or aldehydes depending on the substituents.

Step 5: Combine the products from both cleavages. The final products will include the carbonyl compounds formed from both the exocyclic and ring double bonds. Ensure you account for all fragments generated during the reaction.

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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 chemistry, particularly following ozonolysis. After ozonolysis, the carbonyl compounds can be further reduced to their corresponding alcohols or other derivatives when treated with DMS. This step is crucial for converting the ozonolysis products into more stable or functionalized compounds.

Mechanism of Ozonolysis

The mechanism of ozonolysis involves the formation of a cyclic ozonide intermediate, which is unstable and undergoes cleavage to yield carbonyl compounds. Understanding this mechanism is essential for predicting the products of ozonolysis, as the position of the double bond and the structure of the starting alkene influence the resulting carbonyls. This knowledge is vital for accurately determining the products when analyzing the reaction.

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

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.
c.