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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Problem 29d

Textbook Question

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

Verified step by step guidance

Identify the alkenes in the given structure. In the image, there are two double bonds present in the molecule.

Understand the reaction conditions: Ozonolysis involves the reaction of alkenes with ozone (O₃) followed by a reductive workup with dimethyl sulfide (CH₃SCH₃). This process cleaves the double bonds and forms carbonyl compounds.

For each alkene, draw the ozonolysis intermediate, which is a molozonide that rearranges to an ozonide. However, for simplicity, focus on the final products after reductive workup.

Determine the products formed from each double bond. The first double bond will be cleaved to form two carbonyl compounds, typically aldehydes or ketones, depending on the substituents attached to the double bond.

Repeat the process for the second double bond. Draw the carbonyl compounds formed from the cleavage of the second double bond. Ensure to consider the position of the hydroxyl group in the molecule, as it may affect the final product 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 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. In this question, the alkene undergoes ozonolysis, breaking the double bonds and forming carbonyl groups at the cleavage sites.

Reductive Workup

Reductive workup is a step following ozonolysis where a reducing agent, such as dimethyl sulfide (CH₃SCH₃), is used to convert ozonides into stable carbonyl compounds. This step prevents the formation of carboxylic acids, ensuring that aldehydes or ketones are the final products. In this scenario, CH₃SCH₃ is used to achieve this transformation.

Alkene Structure

Understanding the structure of the alkene is crucial for predicting the ozonolysis products. The given alkene has two double bonds, which will be cleaved during ozonolysis. Each cleavage results in the formation of carbonyl compounds, and the presence of an alcohol group may influence the stability and reactivity of the resulting products.

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Related Practice

Textbook Question

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

(e)

Textbook Question

Propose a synthesis of the carbonyl(s) using the (i) ozonolysis pathways.

(a)

Textbook Question

Propose a synthesis of the carbonyl(s) using the (i) ozonolysis pathways.

(b)

Textbook Question

Predict the reagents or reactant(s) necessary to complete the following syntheses.

(b)

Textbook Question

Predict the product of ozonolysis of the triglyceride shown.

Open Question

Predict the product of the following aldehyde/ketone syntheses.

(a) <IMAGE>

Textbook Question

Predict the product of the following aldehyde/ketone syntheses.

(a)

Textbook Question

Ozonolysis of an unknown alkene A gives the products shown. Predict the product that results from hydrogenation of alkene A. [There are multiple answers, but only show the one with the 6-membered ring.]

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

Key Concepts

Ozonolysis

Reductive Workup

Alkene Structure

Watch next

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