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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4:56 minutes

Problem 30e,f

Textbook Question

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

Verified step by step guidance

Step 1: Understand the reaction mechanism. Ozonolysis is a reaction where ozone (O₃) cleaves double bonds in alkenes to form carbonyl compounds. When followed by dimethyl sulfide (DMS), the reaction reduces the intermediate ozonide to aldehydes or ketones.

Step 2: Analyze the first compound (image e). The structure contains a cyclohexene ring with one double bond and a methyl group attached. The double bond will be cleaved by ozone, splitting the molecule into two fragments.

Step 3: Predict the cleavage products for compound e. The double bond in the cyclohexene ring will break, forming two carbonyl groups. The methyl group remains attached to one of the fragments. Use the position of the double bond to determine the exact products.

Step 4: Analyze the second compound (image f). This structure contains a cyclohexene ring with two double bonds, one in the ring and one in the exocyclic position. Both double bonds will undergo cleavage during ozonolysis.

Step 5: Predict the cleavage products for compound f. The cleavage of the double bond in the ring will produce two carbonyl fragments, while the cleavage of the exocyclic double bond will yield additional carbonyl compounds. Consider the positions of the double bonds to determine the exact products.

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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 involving the cleavage of alkenes or alkynes using ozone (O3) to form carbonyl compounds, such as aldehydes and ketones. The reaction typically occurs in two steps: first, the alkene reacts with ozone to form a molozonide, which rearranges to form ozonides. These ozonides can then be hydrolyzed or treated with a reducing agent, such as dimethyl sulfide, to yield the final carbonyl products.

Dimethyl Sulfide as a Reducing Agent

Dimethyl sulfide (DMS) is often used as a reducing agent in organic reactions, particularly in the reduction of ozonides formed during ozonolysis. DMS can effectively convert ozonides into stable carbonyl compounds by reducing them, which helps to prevent the formation of unwanted byproducts. This step is crucial for obtaining the desired aldehydes or ketones from the ozonolysis process.

Mechanism of Ozone Reaction

The mechanism of the reaction between ozone and alkenes involves the formation of a cyclic intermediate, which is a key step in ozonolysis. This intermediate undergoes rearrangement and cleavage, leading to the formation of carbonyl compounds. Understanding this mechanism is essential for predicting the products of the reaction, as it determines how the original alkene structure is transformed into the final products.

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Related Practice

Textbook Question

Show how you would synthesize each compound using methylenecyclohexane as your starting material.

(d)

Textbook Question

Ozonolysis can be applied selectively to different types of carbon–carbon double bonds. The compound shown below contains two vinyl ether double bonds, which are electron-rich because of the electron-donating alkoxy groups. Ozone reacts more quickly with electron-rich double bonds and more slowly with hindered double bonds. At −78 °C, this compound quickly adds two equivalents of ozone. Immediate reduction of the ozonide gives a good yield of a single product. Show the expected ozonolyis product, and label the functional groups produced, some of which are not typical from ozonolysis of simple alkenes.

Textbook Question

Professor Patrick Dussault (University of Nebraska at Lincoln) has developed an alternative to the standard two-step ozonolysis procedure requiring reduction of the ozonide in a second step. He uses 2 to 3 equivalents of pyridine, a mildly basic organic solvent, in a one-step process (Organic Letters, 2012, 14, 2242). Show the products you expect from the following examples.

(c)

(d)

Textbook Question

Predict the major products of the following reactions.

(c)

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

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