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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3:32 minutes

Problem 30a

Textbook Question

What products are formed when the following compounds react with ozone and then with dimethyl sulfide?
a.

Verified step by step guidance

Step 1: Recognize that the reaction involves ozonolysis followed by reduction with dimethyl sulfide. Ozonolysis cleaves the double bond in the compound, forming two carbonyl compounds (aldehydes or ketones). Dimethyl sulfide is used to reduce the intermediate ozonide to the final carbonyl products.

Step 2: Identify the double bond in the given compound. The structure shows a double bond between the two central carbon atoms in the molecule. This is the site where ozonolysis will occur.

Step 3: Break the double bond and add oxygen atoms to each carbon involved in the double bond. This forms two fragments, each containing a carbonyl group. Use the structure to determine the substituents attached to each carbon and ensure the correct placement of the carbonyl groups.

Step 4: Analyze the substituents on each fragment to determine whether the products are aldehydes or ketones. If the carbon involved in the double bond is bonded to two other carbons, the product will be a ketone. If it is bonded to one carbon and one hydrogen, the product will be an aldehyde.

Step 5: Write the final products formed after ozonolysis and reduction with dimethyl sulfide. Ensure the products are correctly labeled and match the original substituents from the starting compound.

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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 by ozone (O3) to form ozonides, which can then be further processed. This reaction typically results in the formation of carbonyl compounds, such as aldehydes or ketones, depending on the structure of the starting material. Understanding the mechanism of ozonolysis is crucial for predicting the products formed from the reaction of specific compounds.

Dimethyl Sulfide (DMS) as a Reducing Agent

Dimethyl sulfide (DMS) is often used as a reducing agent in organic reactions, particularly in the workup of ozonolysis. After the formation of ozonides, DMS can reduce these intermediates to yield more stable carbonyl compounds. Recognizing the role of DMS in this context is essential for determining the final products of the reaction sequence.

Functional Group Transformation

Functional group transformation refers to the process of converting one functional group into another through chemical reactions. In the context of ozonolysis followed by reduction with DMS, alkenes are transformed into carbonyl-containing compounds. Understanding how different functional groups react and transform is key to predicting the outcomes of organic reactions.

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What products are formed when the following compounds react with ozone and then with dimethyl sulfide? a.

Key Concepts

Ozonolysis

Dimethyl Sulfide (DMS) as a Reducing Agent

Functional Group Transformation

Watch next

What products are formed when the following compounds react with ozone and then with dimethyl sulfide?
a.