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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2:26 minutes

Problem 30c,d

Textbook Question

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

Verified step by step guidance

Step 1: Understand the reaction mechanism. Ozonolysis is a reaction where ozone (O₃) cleaves double bonds in alkenes to form ozonides. These ozonides are then reduced by dimethyl sulfide (DMS) to yield carbonyl compounds (aldehydes or ketones).

Step 2: Analyze the first compound (cyclohexene). Cyclohexene contains one double bond in a six-membered ring. Ozone will cleave this double bond, splitting the ring into two fragments. Each fragment will form a carbonyl group.

Step 3: Predict the products for cyclohexene. After ozonolysis and reduction with dimethyl sulfide, the two fragments will be converted into two molecules of formaldehyde (CH₂O).

Step 4: Analyze the second compound (methylcyclohexene). Methylcyclohexene contains a double bond in a six-membered ring with a methyl group attached. Ozone will cleave the double bond, splitting the ring into two fragments. One fragment will contain the methyl group, and the other will not.

Step 5: Predict the products for methylcyclohexene. After ozonolysis and reduction with dimethyl sulfide, the fragment with the methyl group will form acetaldehyde (CH₃CHO), and the other fragment will form formaldehyde (CH₂O).

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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 ozonides. These ozonides can then be hydrolyzed or treated with a reducing agent, such as dimethyl sulfide, to yield the final carbonyl products.

Dimethyl Sulfide as a Reducing Agent

Dimethyl sulfide (DMS) is often used as a reducing agent in organic reactions, particularly in the reduction of ozonides formed during ozonolysis. DMS can effectively convert ozonides into stable carbonyl compounds by reducing them, thus preventing the formation of potentially unstable intermediates. This step is crucial for obtaining the desired products from the ozonolysis reaction.

Carbonyl Compounds

Carbonyl compounds, which include aldehydes and ketones, are characterized by the presence of a carbonyl group (C=O). The formation of these compounds is a key outcome of ozonolysis reactions. Understanding the structure and reactivity of carbonyl compounds is essential for predicting the products of reactions involving ozone and dimethyl sulfide, as they play a significant role in various organic transformations.

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Related Practice

Textbook Question

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

Textbook Question

What alkene gives the product shown after reaction first with ozone and then with dimethyl sulfide?

Textbook Question

What alkene gives the product shown after reaction first with ozone and then with dimethyl sulfide?

Textbook Question

The following products were obtained from the oxidative cleavage of a diene. What is the structure of the diene?

Textbook Question

The following product was obtained from the ozonolysis of an alkene followed by treatment with dimethyl sulfide. What is the structure of the alkene?

Textbook Question

The following product was obtained from the ozonolysis of an alkene followed by treatment with dimethyl sulfide. What is the structure of the alkene?

Textbook Question

One of the constituents of turpentine is α-pinene, formula C₁₀H₆. The following scheme (called a “road map”) gives some reactions of α-pinene. Determine the structure of α-pinene and of the reaction products of A through E.

Textbook Question

Problem 8-54 describes a new method to perform ozonolysis reactions that used pyridine (py) to generate the final aldehydes and ketones in a non-aqueous reaction medium. In a subsequent publication (J. Org. Chem., 2013, 78, 42), Professor Dussault (U. of Nebraska at Lincoln) described a “tandem” process in which two reactions are performed sequentially without having to isolate the intermediate aldehyde or ketone. Show the final product from each sequence. (Hint: The isolated products were from the larger part of the structure. Ignore stereochemistry.)

(a)

(b)

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

Key Concepts

Ozonolysis

Dimethyl Sulfide as a Reducing Agent

Carbonyl Compounds

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