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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2:57 minutes

Problem 103b

Textbook Question

Ozonolysis of an alkene, followed by treatment with dimethyl sulfide, forms the following product(s). Identify the alkene in each case.
b.

Verified step by step guidance

Step 1: Understand the reaction. Ozonolysis is a reaction where an alkene reacts with ozone (O₃) to form an ozonide intermediate. This intermediate is then reduced using a reducing agent, such as dimethyl sulfide (DMS), to yield carbonyl compounds (aldehydes or ketones).

Step 2: Analyze the given product(s). Identify the carbonyl compounds (aldehydes or ketones) formed after the ozonolysis and reduction steps. These products will help you deduce the structure of the original alkene.

Step 3: Reconstruct the alkene. Combine the carbonyl compounds by 'reversing' the cleavage process. Connect the carbon atoms of the carbonyl groups at the positions where the double bond was originally present in the alkene.

Step 4: Ensure the correct structure. Verify that the reconstructed alkene has the correct number of carbons and matches the connectivity implied by the carbonyl products. Also, ensure that the stereochemistry (if applicable) is consistent with the reaction conditions.

Step 5: Confirm the answer. Double-check the reaction mechanism to ensure that the proposed alkene would indeed produce the given carbonyl products upon 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 ozonides, which can then be further reduced. This reaction typically results in the formation of carbonyl compounds, such as aldehydes or ketones, depending on the structure of the alkene. Understanding ozonolysis is crucial for predicting the products formed from specific alkenes.

Dimethyl Sulfide (DMS) Reduction

Dimethyl sulfide (DMS) is commonly used as a reducing agent in organic chemistry, particularly in the reduction of ozonides formed during ozonolysis. The treatment of ozonides with DMS converts them into more stable carbonyl compounds, allowing for the identification of the original alkene. Recognizing the role of DMS is essential for understanding the final products of ozonolysis.

Alkene Structure and Reactivity

The structure of alkenes, characterized by a carbon-carbon double bond, significantly influences their reactivity in reactions like ozonolysis. Factors such as substitution patterns (e.g., whether the alkene is terminal or internal) affect the products formed during ozonolysis. A solid grasp of alkene structures is necessary to deduce the original alkene from the products generated in the reaction.

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Master General properties of ozonolysis. with a bite sized video explanation from Johnny

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Ozonolysis of an alkene, followed by treatment with dimethyl sulfide, forms the following product(s). Identify the alkene in each case. b.

Key Concepts

Ozonolysis

Dimethyl Sulfide (DMS) Reduction

Alkene Structure and Reactivity

Watch next

Ozonolysis of an alkene, followed by treatment with dimethyl sulfide, forms the following product(s). Identify the alkene in each case.
b.