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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4:29 minutes

Problem 29c

Textbook Question

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

Verified step by step guidance

Identify the alkene in the given structure. The double bond is located between the two carbon atoms at the top of the structure.

Understand the reaction: Ozonolysis is a reaction where ozone (O₃) cleaves the double bond of an alkene, forming two carbonyl groups. The use of dimethyl sulfide (CH₃SCH₃) as a reducing agent will ensure that the carbonyl groups remain as aldehydes or ketones.

Draw the structure of the alkene with the double bond cleaved. This involves breaking the double bond and adding an oxygen atom to each of the carbon atoms that were originally part of the double bond.

Determine the type of carbonyl groups formed: If the carbon atom is bonded to two other carbon atoms, a ketone is formed. If it is bonded to one carbon and one hydrogen, an aldehyde is formed.

Draw the final products: Based on the structure, identify and draw the aldehyde and/or ketone products that result from the ozonolysis reaction.

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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 reaction involves the formation of an ozonide intermediate, which is then reduced to yield aldehydes or ketones. In this context, the alkene is treated with O₃, followed by a reducing agent like CH₃SCH₃, to break the double bond and form the corresponding carbonyl products.

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 or other oxidized products, ensuring that the reaction yields aldehydes or ketones, depending on the structure of the original alkene.

Alkene Structure and Reactivity

The structure of the alkene determines the products formed during ozonolysis. In the given image, the alkene has a terminal double bond and a cyclopentene ring. The ozonolysis will cleave the double bond, resulting in the formation of a ketone from the terminal alkene and an aldehyde from the cyclopentene, reflecting the positions of the double bonds in the original structure.

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Related Practice

Textbook Question

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

(b)

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

What alkenes would give only an aldehyde with four carbons as a product of oxidative cleavage

Textbook Question

What are the products of the following reactions? Indicate whether each reaction is an oxidation or a reduction.

Textbook Question

What are the products of the following reactions? Indicate whether each reaction is an oxidation or a reduction.

Textbook Question

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

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

Key Concepts

Ozonolysis

Reductive Workup

Alkene Structure and Reactivity

Watch next

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