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

Previous problemNext problem

4:01 minutes

Problem 45d(viii)

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)

Verified step by step guidance

Step 1: Recognize the reaction type. The given conditions (1. O₃ and 2. CH₃SCH₃) indicate an ozonolysis reaction, which is used to cleave alkenes at the double bond and form carbonyl compounds.

Step 2: Understand the mechanism. Ozone (O₃) reacts with the alkene to form an unstable intermediate called a molozonide, which rearranges to form an ozonide. The ozonide is then reduced by dimethyl sulfide (CH₃SCH₃) to yield aldehydes and/or ketones.

Step 3: Identify the structure of the alkene. Analyze the given alkene structure to determine the location of the double bond. This will help predict the cleavage points and the resulting fragments.

Step 4: Break the double bond. Split the alkene at the double bond, and add oxygen atoms to each carbon involved in the double bond to form carbonyl groups (C=O).

Step 5: Determine the products. Based on the cleavage and addition of oxygen atoms, identify whether the resulting compounds are aldehydes or ketones. Ensure that the products match the original structure of the alkene.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

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. The process typically occurs in two steps: first, the alkene reacts with ozone to form a molozonide, which rearranges to form ozonide. This ozonide can then be reduced to aldehydes or ketones, depending on the structure of the original alkene.

Thioether Reduction

In the context of organic reactions, thioethers like dimethyl sulfide (CH₃SCH₃) can act as reducing agents. When used in conjunction with ozonolysis, thioethers can help convert the ozonide intermediate into more stable products, often resulting in the formation of alcohols or other functional groups, depending on the reaction conditions.

Regioselectivity

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In ozonolysis, the regioselectivity of the reaction can influence the types of carbonyl compounds formed, as the position of the double bond in the alkene will determine the sites of cleavage and the resulting products.

Watch next

Master General properties of ozonolysis. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

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

(a)

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

(h)

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

(k)

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)

Show more practices