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 29b

Textbook Question

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

Verified step by step guidance

Identify the alkene in the given structure. The double bond is located between the two carbon atoms connecting the isopropyl group and the cyclohexane ring.

Understand that ozonolysis involves the cleavage of the carbon-carbon double bond. Ozone (O₃) will react with the alkene to form an ozonide intermediate.

Recognize that the ozonide intermediate will be reduced by dimethyl sulfide (CH₃SCH₃) to form carbonyl compounds. Each carbon of the former double bond will become a carbonyl group.

Draw the products by replacing the double-bonded carbons with carbonyl groups. The isopropyl group will be attached to an aldehyde, and the cyclohexane ring will be attached to a ketone.

Ensure that the final structures are correctly drawn, showing an aldehyde and a ketone as the products of the ozonolysis reaction followed by reduction with dimethyl sulfide.

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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. This reaction is useful for breaking down complex alkenes into simpler, identifiable fragments.

Reductive Workup

Reductive workup in ozonolysis involves using a reducing agent, such as dimethyl sulfide (CH₃SCH₃), to convert the ozonide intermediate into stable carbonyl compounds. This step prevents the formation of carboxylic acids, ensuring that aldehydes are produced instead, which is crucial for maintaining the integrity of the original carbon skeleton.

Alkene Structure

Understanding the structure of the alkene is essential for predicting the products of ozonolysis. The alkene in the image is a cyclohexene with an isopropyl group attached, indicating that ozonolysis will cleave the double bond, resulting in two carbonyl compounds: an aldehyde from the isopropyl group and a ketone from the cyclohexene ring.

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Related Practice

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.]

Textbook Question

Suggest reagents to carry out the following transformation.

Textbook Question

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

(b)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vii) 1. mCPBA 2. H₂SO₄, H₂O (viii) 1. O₃ 2. CH₃SCH₃

(l)

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

(f)

Textbook Question

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

(c)

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