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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2:50 minutes

Problem 31

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?

Verified step by step guidance

Understand the process of ozonolysis: Ozonolysis is a reaction where alkenes are cleaved by ozone (O₃) to form carbonyl compounds. The double bond in the alkene is broken, and each carbon atom of the double bond is converted into a carbonyl group.

Identify the products: The problem states that the products of ozonolysis are acetophenone and acetaldehyde. Acetophenone is a ketone with the formula C₆H₅C(O)CH₃, and acetaldehyde is an aldehyde with the formula CH₃CHO.

Determine the structure of the original alkene: To produce acetophenone and acetaldehyde, the alkene must have a structure that, when cleaved, results in these two carbonyl compounds. Consider the carbon atoms that form the double bond in the alkene and how they relate to the carbonyl groups in the products.

Consider alternative alkene structures: The problem suggests there is another alkene that can produce the same products. Think about different ways to arrange the carbon atoms in the alkene that would still result in acetophenone and acetaldehyde upon ozonolysis. This involves considering different positions for the double bond and the surrounding carbon atoms.

Verify the alternative structure: Once you have proposed an alternative alkene structure, ensure that when it undergoes ozonolysis, it indeed produces acetophenone and acetaldehyde. This involves checking that the cleavage of the double bond leads to the correct carbonyl groups.

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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. Understanding the mechanism of ozonolysis is crucial for predicting the products formed from specific alkenes.

Alkene Structure

The structure of an alkene, including its substituents and position of double bonds, determines the products formed during ozonolysis. Identifying the correct alkene involves understanding how different structural isomers can lead to the same set of carbonyl compounds, such as acetophenone and acetaldehyde.

Carbonyl Compound Formation

Carbonyl compounds, such as ketones and aldehydes, are the typical products of ozonolysis. Acetophenone and acetaldehyde are specific examples, and recognizing how these compounds can be derived from different alkenes is essential. This involves understanding the cleavage of the double bond and the subsequent rearrangement of atoms.

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Related Practice

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

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

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)

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)

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