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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4:55 minutes

Problem 75

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.

Verified step by step guidance

Step 1: Analyze the structure of the compound provided. The molecule contains two vinyl ether double bonds, which are electron-rich due to the electron-donating alkoxy groups (-OCH3). These double bonds are more reactive toward ozone compared to hindered or less electron-rich double bonds.

Step 2: Understand the reaction conditions. Ozonolysis involves the addition of ozone (O3) to the double bonds at low temperatures (-78 °C). The reaction proceeds by forming an ozonide intermediate, which is then reduced using dimethyl sulfide ((CH3)2S) to yield the final products.

Step 3: Predict the cleavage of the double bonds. Ozone cleaves the carbon-carbon double bonds, resulting in the formation of carbonyl-containing products. For vinyl ethers, ozonolysis typically produces aldehydes or ketones, along with other functional groups depending on the substituents.

Step 4: Identify the products formed. Each double bond in the molecule will be cleaved, and the electron-donating alkoxy groups will influence the type of carbonyl compounds formed. The expected products will include aldehydes and/or ketones, and the functional groups should be labeled accordingly.

Step 5: Summarize the functional groups in the product. After ozonolysis and reduction, the molecule will yield a single product containing multiple carbonyl groups (aldehydes and/or ketones). These functional groups are characteristic of ozonolysis reactions, but the presence of alkoxy groups may lead to atypical products compared to simple alkenes.

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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 carbon-carbon double bonds (alkenes) using ozone (O3). This reaction typically results in the formation of ozonides, which can be further reduced to yield carbonyl compounds such as aldehydes or ketones. The reaction is particularly useful for transforming alkenes into more functionalized products, and the selectivity of ozonolysis can vary based on the electronic and steric properties of the double bonds involved.

Electron-Rich Double Bonds

Electron-rich double bonds, such as those found in vinyl ethers, are more reactive towards ozone due to the presence of electron-donating groups. These groups enhance the nucleophilicity of the double bond, facilitating a faster reaction with ozone compared to electron-poor or hindered double bonds. Understanding the reactivity of different double bonds is crucial for predicting the products of ozonolysis and the overall reaction mechanism.

Functional Group Transformation

Ozonolysis often leads to the formation of functional groups that are not typically associated with simple alkenes. In this reaction, the cleavage of the double bond can produce carbonyl compounds, such as aldehydes and ketones, as well as other functional groups depending on the substituents present. Recognizing these transformations is essential for accurately predicting the final products of ozonolysis and understanding the implications for further chemical reactivity.

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Related Practice

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.

(a)

(b)

Textbook Question

Give structures of the alkenes that would give the following products upon ozonolysis–reduction.

(c)

Textbook Question

Using 1,2-dimethylcyclohexene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) If a chiral product is shown, assume that it is part of a racemic mixture.

(i)

Textbook Question

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

(d)

Textbook Question

(c)

(d)

Textbook Question

Predict the major products of the following reactions.

(c)

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

Textbook Question