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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5:44 minutes

Problem 85b

Textbook Question

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

Verified step by step guidance

Step 1: Identify the functional group in the given compound. The structure provided is a cyclohexene ring with a methyl group attached to one of the carbons. The double bond in the cyclohexene ring is the site of ozonolysis.

Step 2: Understand the ozonolysis reaction. Ozonolysis involves the cleavage of the double bond in the presence of ozone (O₃), forming an ozonide intermediate. This intermediate is then treated with a reducing agent, such as dimethyl sulfide (DMS), to yield carbonyl compounds.

Step 3: Break the double bond in the cyclohexene ring. The double bond will split into two fragments, and each carbon involved in the double bond will form a carbonyl group (either an aldehyde or a ketone).

Step 4: Analyze the structure after cleavage. The double bond in the cyclohexene ring splits into two carbonyl groups. The methyl group remains attached to one of the carbons, and the ring structure is opened.

Step 5: Write the products. The products of ozonolysis followed by treatment with dimethyl sulfide will be two carbonyl compounds. Specifically, one will be a ketone due to the methyl group, and the other will be an aldehyde. Ensure the correct placement of the functional groups based on the original structure.

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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 proceeds through the formation of a molozonide intermediate, which rearranges to form ozonides. This process is crucial for determining the structure of unsaturated compounds and is often followed by reductive workup to yield stable products.

Dimethyl Sulfide (DMS) Treatment

Dimethyl sulfide (DMS) is commonly used as a reducing agent in organic chemistry, particularly following ozonolysis. After ozonolysis, DMS reduces the ozonide intermediates to yield aldehydes or ketones, effectively stabilizing the products. This step is essential for preventing the formation of unwanted byproducts and ensuring that the desired carbonyl compounds are obtained.

Cyclohexane Derivatives

Cyclohexane derivatives are compounds that contain a cyclohexane ring with various substituents. The structure of these derivatives influences their reactivity in reactions such as ozonolysis. Understanding the positioning and nature of substituents on the cyclohexane ring is vital for predicting the products formed during ozonolysis and subsequent reactions, as they can affect sterics and electronic properties.

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

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

Key Concepts

Ozonolysis

Dimethyl Sulfide (DMS) Treatment

Cyclohexane Derivatives

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