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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1:19 minutes

Problem 34b

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?
b.

Verified step by step guidance

Step 1: Understand the reaction. Ozonolysis is a reaction where an alkene is cleaved by ozone (O₃), resulting in the formation of carbonyl compounds. When followed by treatment with dimethyl sulfide (DMS), the ozonide intermediate is reduced to aldehydes or ketones.

Step 2: Analyze the product structure. The image shows two ketones: acetone (CH₃COCH₃) on both sides. This indicates that the original alkene was symmetrical and cleaved into two identical fragments.

Step 3: Recall the ozonolysis mechanism. The double bond in the alkene is cleaved, and each carbon of the double bond becomes part of a carbonyl group. Since the product contains two identical ketones, the alkene must have been symmetrical.

Step 4: Deduce the structure of the alkene. To form two molecules of acetone, the original alkene must have been 2,3-dimethyl-2-butene. This is because the cleavage of the double bond in this alkene would yield two identical acetone molecules.

Step 5: Verify the reasoning. The symmetry of the alkene ensures that ozonolysis produces identical fragments. The presence of dimethyl sulfide ensures the reduction of the ozonide intermediate to ketones, confirming the structure of the alkene.

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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 carbonyl compounds, such as aldehydes and ketones. The process 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 reduced to yield the final carbonyl products, providing insight into the structure of the original alkene.

Dimethyl Sulfide (DMS) Reduction

Dimethyl sulfide (DMS) is often used as a reducing agent in organic chemistry, particularly in the context of ozonolysis. After the formation of carbonyl compounds from ozonolysis, DMS can reduce ozonides to yield stable aldehydes or ketones. Understanding this reduction step is crucial for determining the final products and, consequently, the structure of the original alkene.

Alkene Structure and Isomerism

The structure of alkenes is characterized by the presence of a carbon-carbon double bond, which can lead to geometric isomerism (cis/trans) and structural isomerism. Recognizing the possible configurations and substituents around the double bond is essential for deducing the original alkene from the products formed during ozonolysis. This understanding aids in predicting the outcomes of reactions involving alkenes.

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Related Practice

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

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

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)

Textbook Question

(c)

(d)

Textbook Question

Deduce the structure of each compound from the information given. All unknowns in this problem have molecular formula C₈H₁₂.

(c) Upon catalytic hydrogenation, unknown Y gives cyclooctane. Ozonolysis of Y, followed by reduction with dimethyl sulfide, gives a three-carbon dialdehyde and a five-carbon dialdehyde. Draw the structure of Y.

(d) Upon catalytic hydrogenation, unknown Z gives cis-bicyclo[4.2.0]octane. Ozonolysis of Z, followed by reduction with dimethyl sulfide, gives a cyclobutane with a three-carbon aldehyde (–CH₂–CH₂–CHO) group on C1 and a one-carbon aldehyde (–CHO) group on C2. Draw the structure of Z.

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

Key Concepts

Ozonolysis

Dimethyl Sulfide (DMS) Reduction

Alkene Structure and Isomerism

Watch next

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