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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2:03 minutes

Problem 32

Textbook Question

What aspect of the structure of the alkene does ozonolysis not tell you?

Verified step by step guidance

Ozonolysis is a reaction where an alkene is cleaved by ozone (O₃) to form carbonyl compounds (aldehydes or ketones). This reaction is useful for determining the positions of double bonds in an alkene.

When an alkene undergoes ozonolysis, the double bond is broken, and each carbon atom of the double bond is converted into a carbonyl group. The products provide information about the connectivity of the carbon atoms around the double bond.

However, ozonolysis does not provide information about the stereochemistry of the alkene. Specifically, it does not reveal whether the original alkene was in the cis (Z) or trans (E) configuration.

This limitation arises because the cleavage of the double bond during ozonolysis eliminates any stereochemical information. The products are the same regardless of whether the starting alkene was cis or trans.

To determine the stereochemistry of an alkene, other methods such as spectroscopic techniques (e.g., NMR) or reactions that preserve stereochemistry would need to be used.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Alkene Structure

Alkenes are hydrocarbons characterized by at least one carbon-carbon double bond (C=C). This double bond influences their reactivity and geometry, leading to unique properties such as cis-trans isomerism. Understanding the specific arrangement of substituents around the double bond is crucial for predicting the outcomes of reactions involving alkenes.

Ozonolysis

Ozonolysis is a reaction involving the cleavage of carbon-carbon double bonds using ozone (O3), resulting in the formation of carbonyl compounds such as aldehydes and ketones. While this reaction provides information about the products formed from the alkene, it does not reveal the stereochemistry or the specific arrangement of substituents around the double bond, which are essential for understanding the alkene's structure.

Stereochemistry

Stereochemistry refers to the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the context of alkenes, stereochemistry is important because the configuration of substituents around the double bond can lead to different isomers with distinct properties. Ozonolysis does not provide information about these configurations, which are critical for understanding the reactivity and characteristics of the alkene.

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Related Practice

Textbook Question

Predict the major products of the following reactions.

(c)

(d) 1-ethylcycloheptene + ozone, then (CH₃)₂S

Textbook Question

What products are formed when the following compounds react with ozone and then with dimethyl sulfide?

Textbook Question

Ozonolysis of an alkene, followed by treatment with dimethyl sulfide, forms the following product(s). Identify the alkene in each case.

Textbook Question

What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?

d. O₃, −78 °C, followed by (CH₃)₂S

Textbook Question

What reagents are needed to carry out the following syntheses?

Textbook Question

In contact with a platinum catalyst, an unknown alkene reacts with three equivalents of hydrogen gas to give 1-isopropyl-4-methylcyclohexane. When the unknown alkene is ozonized and reduced, the products are the following:

Deduce the structure of the unknown alkene.

Multiple Choice

Predict the products of the following reaction.

Multiple Choice

Suggest a starting material that will form the following products upon ozonolysis.

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