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

11. Radical Reactions

Radical Reaction

Organic Chemistry

11. Radical Reactions

Radical Reaction

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5:30 minutes

Problem 46e

Textbook Question

Using cyclohexane as one of your starting materials, show how you would synthesize the following compounds.
(e)

Verified step by step guidance

Step 1: Begin with cyclohexane as the starting material. Cyclohexane is a saturated hydrocarbon with the molecular formula C6H12. To introduce a functional group, you need to activate one of the hydrogens on the ring.

Step 2: Perform a free radical halogenation reaction using bromine (Br2) and light (hv) or heat. This will replace one hydrogen atom on the cyclohexane ring with a bromine atom, forming bromocyclohexane.

Step 3: Prepare a nucleophile for substitution. Use methoxide ion (CH3O⁻), which can be generated from sodium methoxide (NaOCH3) in methanol. Methoxide is a strong nucleophile and will readily participate in a substitution reaction.

Step 4: Perform an SN2 reaction between bromocyclohexane and methoxide ion. The bromine atom will be replaced by the methoxy group (-OCH3), resulting in the formation of methoxycyclohexane.

Step 5: Purify the product using standard organic chemistry techniques such as distillation or recrystallization to isolate methoxycyclohexane.

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Key Concepts

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

Cyclohexane Structure and Reactivity

Cyclohexane is a six-membered carbon ring that is saturated, meaning it contains only single bonds. Its stable chair conformation minimizes steric strain, making it a common starting material in organic synthesis. Understanding its structure is crucial for predicting how it will react in various chemical transformations, including substitution and radical reactions.

Radical Reactions

Radical reactions involve species with unpaired electrons, known as radicals, which can initiate chain reactions. In the context of synthesizing compounds from cyclohexane, radical halogenation can introduce functional groups like methoxy (OCH3) through the abstraction of hydrogen atoms. Mastery of radical mechanisms is essential for designing effective synthetic pathways.

Functional Group Transformation

Functional group transformation refers to the process of converting one functional group into another, which is a key aspect of organic synthesis. In this case, converting cyclohexane into a methoxy-substituted cyclohexane involves introducing an ether group. Understanding the reactivity and compatibility of different functional groups is vital for successful synthesis.

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