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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3:47 minutes

Problem 51d

Textbook Question

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

(d)

Verified step by step guidance

Step 1: Begin with methylenecyclohexane as the starting material. This compound contains a double bond, which can be used for functional group transformations.

Step 2: Perform an ozonolysis reaction on methylenecyclohexane. Ozonolysis involves the cleavage of the double bond using ozone (O₃), followed by a reductive workup (e.g., using zinc and acetic acid or dimethyl sulfide). This reaction will yield a ketone and/or aldehyde depending on the structure of the alkene.

Step 3: In this case, ozonolysis of methylenecyclohexane will produce cyclohexanone. The double bond is cleaved, and the carbon attached to the double bond is oxidized to a ketone functional group.

Step 4: Verify the product structure. Cyclohexanone is a six-membered ring with a ketone group at one of the carbons. Ensure the reaction conditions are optimized to avoid overoxidation or side reactions.

Step 5: Purify the cyclohexanone product using techniques such as distillation or recrystallization, depending on the reaction scale and purity requirements.

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Key Concepts

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

Synthesis of Organic Compounds

The synthesis of organic compounds involves creating complex molecules from simpler ones through various chemical reactions. Understanding the mechanisms of these reactions, such as addition, elimination, and substitution, is crucial for designing synthetic pathways. In this context, starting from methylenecyclohexane, one must consider how to manipulate its double bond and ring structure to form the desired products.

Ozonolysis

Ozonolysis is a reaction involving the cleavage of alkenes or alkynes using ozone (O3), resulting in the formation of carbonyl compounds such as aldehydes or ketones. This reaction is particularly useful for synthesizing compounds with functional groups from unsaturated hydrocarbons. In the context of the question, ozonolysis can be applied to methylenecyclohexane to generate intermediates that can be further transformed into the target compounds.

Functional Group Transformation

Functional group transformation refers to the process of converting one functional group into another through chemical reactions. This concept is essential in organic synthesis as it allows chemists to modify the reactivity and properties of molecules. In synthesizing compounds from methylenecyclohexane, understanding how to effectively change functional groups, such as converting alkenes to carbonyls, is key to achieving the desired structures.

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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.

(d)

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

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

(c)

(d)

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?

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