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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7:37 minutes

Problem 33

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.

Verified step by step guidance

Understand the concept of ozonolysis: Ozonolysis is a reaction where ozone (O₃) cleaves alkenes to form carbonyl compounds. The initial step involves the formation of a molozonide, which is a cyclic intermediate.

Recognize stereospecificity: Stereospecific reactions lead to different stereoisomers depending on the configuration of the starting material. In this case, the stereochemistry of the alkene affects the stereochemistry of the molozonide formed.

Identify the starting materials: The problem involves (E)- and (Z)-3,4-dimethylhept-3-ene. The (E)-isomer has the two methyl groups on opposite sides of the double bond, while the (Z)-isomer has them on the same side.

Predict the molozonide formation: For the (E)-isomer, the molozonide will form with the substituents on opposite sides, maintaining the stereochemistry. For the (Z)-isomer, the molozonide will form with the substituents on the same side.

Draw the structures: Use the stereochemistry of the starting alkenes to draw the two different molozonides. Ensure that the cyclic structure reflects the stereochemistry of the original alkene, with the oxygen atoms forming a five-membered ring with the carbon atoms from the double bond.

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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. It involves the formation of an intermediate called molozonide, which rearranges to form ozonide before breaking down into aldehydes or ketones. Understanding the mechanism of ozonolysis is crucial for predicting the stereochemistry of the products formed from different alkenes.

Stereospecificity

Stereospecificity refers to a reaction where the stereochemistry of the reactant determines the stereochemistry of the product. In the context of ozonolysis, the stereochemistry of the alkene (E or Z configuration) influences the formation of molozonide, leading to different stereochemical outcomes. This concept is essential for predicting the stereochemical nature of the molozonides formed from (E)- and (Z)-3,4-dimethylhept-3-ene.

E/Z Isomerism

E/Z isomerism is a type of stereoisomerism found in alkenes, where the spatial arrangement of substituents around the double bond differs. E (entgegen) isomers have substituents on opposite sides, while Z (zusammen) isomers have them on the same side. This isomerism affects the stereospecific formation of molozonides during ozonolysis, as the initial geometry of the alkene dictates the stereochemistry of the resulting products.

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Related Practice

Textbook Question

Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate.

(l)

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

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

(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)

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