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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1:04 minutes

Problem 29a

Textbook Question

Draw the product(s) you'd expect when each of these alkenes is treated first with O₃, then with CH₃SCH₃
(a)

Verified step by step guidance

Step 1: Understand the reaction mechanism. The process described involves ozonolysis, a reaction where ozone (O₃) is used to cleave alkenes, followed by a reductive workup with dimethyl sulfide (CH₃SCH₃). This sequence typically results in the formation of carbonyl compounds.

Step 2: Identify the structure of the alkene. Begin by examining the structure of the alkene provided in the problem. Determine the position of the double bond, as this will dictate where the cleavage occurs.

Step 3: Apply ozonolysis. When the alkene is treated with ozone, the double bond is cleaved, and each carbon atom involved in the double bond is converted into a carbonyl group. This results in the formation of two separate fragments, each containing a carbonyl group.

Step 4: Consider the reductive workup. The use of dimethyl sulfide (CH₃SCH₃) in the second step is crucial for the reductive workup. It helps to convert any ozonide intermediates into stable carbonyl compounds, typically aldehydes or ketones, depending on the structure of the original alkene.

Step 5: Draw the final products. Based on the cleavage of the double bond and the formation of carbonyl groups, draw the expected products. Ensure that each fragment from the original alkene is represented as a separate carbonyl compound, reflecting the transformation that occurs during ozonolysis followed by reductive workup.

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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 where ozone (O₃) cleaves alkenes to form carbonyl compounds. The process involves the formation of an ozonide intermediate, which is then reduced to yield aldehydes or ketones, depending on the substitution pattern of the alkene. This reaction is useful for determining the position of double bonds in alkenes.

Reductive Workup

Reductive workup refers to the treatment of ozonolysis intermediates with a reducing agent, such as dimethyl sulfide (Ch₃SCH₃), to convert ozonides into stable carbonyl compounds. This step prevents the formation of carboxylic acids or other oxidized products, ensuring the generation of aldehydes or ketones from the ozonolysis process.

Alkene Structure

The structure of the alkene, including the position and substitution of the double bond, determines the type and number of carbonyl products formed during ozonolysis. Terminal alkenes typically yield aldehydes, while internal alkenes can produce ketones. Understanding the alkene's structure is crucial for predicting the ozonolysis products accurately.

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Related Practice

Textbook Question

Limonene is one of the compounds that give lemons their tangy odor. Show the structures of the products expected when limonene reacts with an excess of each of these reagents.

Textbook Question

Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate.

(l)

Textbook Question

Predict the major products of the following reactions.

(a) (E)-3-methyloct-3-ene + ozone, then (CH₃)₂S

Textbook Question

When compound Z is treated with ozone, followed by dimethyl sulfide and washing with water, the products are formic acid, 3-oxobutanoic acid, and hexanal.

Propose a structure for compound Z. What uncertainty is there in the structure you have proposed?

Textbook Question

Formation of the molozonide can be expected to proceed stereospecifically. Why is this the case? Show the two different molozonides you would expect to get from ozonolysis of (E)- and (Z)-3,4-dimethylhept-3-ene.

Textbook Question

In Solved Assessment 9.30(b), we came up with an alkene that under the conditions of ozonolysis would produce acetophenone and acetaldehyde. There is one other alkene that should produce the same compounds under these conditions. Which is it?

Textbook Question

Suggest a synthesis of the following aldehydes or ketones using the ozonolysis reaction of an alkene.

(a)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (viii) 1. O₃ 2. CH₃SCH₃

(d)

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Draw the product(s) you'd expect when each of these alkenes is treated first with O3, then with CH3SCH3 (a)

Key Concepts

Ozonolysis

Reductive Workup

Alkene Structure

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Draw the product(s) you'd expect when each of these alkenes is treated first with O₃, then with CH₃SCH₃
(a)