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

14. Synthetic Techniques

Moving Functionality

Organic Chemistry

14. Synthetic Techniques

Moving Functionality

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3:24 minutes

Problem 51i

Textbook Question

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

(i)

Verified step by step guidance

Step 1: Analyze the target compound. The target compound is a ketone, specifically 1-methylcyclohexanone. This indicates that the double bond in methylenecyclohexane must undergo oxidation to form a ketone functional group.

Step 2: Select an appropriate oxidation reaction. To convert the alkene in methylenecyclohexane to a ketone, use an ozonolysis reaction followed by reductive workup. Ozonolysis cleaves the double bond and forms a ketone at the terminal carbon.

Step 3: Perform ozonolysis. React methylenecyclohexane with ozone (O₃) in the presence of a solvent like dichloromethane at low temperatures. This will generate an intermediate ozonide.

Step 4: Carry out reductive workup. Treat the ozonide intermediate with a reducing agent such as zinc (Zn) in acetic acid or dimethyl sulfide (DMS). This step will yield the desired ketone, 1-methylcyclohexanone.

Step 5: Verify the product. Confirm the structure of the synthesized compound using spectroscopic techniques such as IR (to identify the carbonyl group) and NMR (to confirm the methyl group and cyclohexane ring).

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Key Concepts

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

Synthetic Pathways

Synthetic pathways refer to the series of chemical reactions that transform a starting material into a desired product. Understanding these pathways is crucial for planning the synthesis of compounds, as it involves selecting appropriate reagents and conditions to achieve the desired transformations while considering factors like yield and selectivity.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Identifying and manipulating functional groups in methylenecyclohexane is essential for synthesizing new compounds, as they dictate the reactivity and properties of the resulting products.

Reagents and Reaction Conditions

Reagents are substances used to bring about a chemical reaction, while reaction conditions include factors such as temperature, pressure, and solvent choice. Selecting the right reagents and optimizing reaction conditions are vital for successful synthesis, as they influence the efficiency and outcome of the reactions involving methylenecyclohexane.

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