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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4:58 minutes

Problem 40b

Textbook Question

Starting with cyclohexane, how could the following compounds be prepared?
b.

Verified step by step guidance

Step 1: Begin with cyclohexane as the starting material. Cyclohexane is a saturated hydrocarbon with no double bonds or functional groups.

Step 2: Perform a bromination reaction to introduce a bromine atom onto the cyclohexane ring. This can be achieved using Br₂ in the presence of UV light, which facilitates a free radical substitution reaction. This step will yield bromocyclohexane.

Step 3: Dehydrohalogenation is required to introduce a double bond into the ring structure. Treat bromocyclohexane with a strong base, such as KOH or NaOH, in an alcoholic solution. The base will abstract a proton from a β-carbon, leading to the elimination of HBr and forming cyclohexene.

Step 4: Bromination of cyclohexene is necessary to add a bromine atom to the allylic position (the carbon adjacent to the double bond). Use NBS (N-bromosuccinimide) in the presence of light or heat to selectively brominate the allylic position, yielding the desired compound.

Step 5: Verify the structure of the final product, which should be 3-bromocyclohexene, ensuring the bromine atom is at the allylic position relative to the double bond.

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Key Concepts

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

Radical Reactions

Radical reactions involve the formation and reaction of free radicals, which are highly reactive species with unpaired electrons. In the context of bromocyclohexane synthesis, a radical halogenation reaction can be initiated by heat or light, leading to the substitution of a hydrogen atom in cyclohexane with a bromine atom, resulting in bromocyclohexane.

Electrophilic Substitution

Electrophilic substitution is a key mechanism in organic chemistry where an electrophile replaces a hydrogen atom in an aromatic compound. Although cyclohexane is not aromatic, understanding this concept is crucial for recognizing how similar mechanisms can apply to cyclic compounds, especially when considering the reactivity of substituted cyclohexanes in further reactions.

Mechanism of Halogenation

The mechanism of halogenation typically involves the generation of a halogen radical, which then abstracts a hydrogen atom from the alkane, forming a new radical. This new radical can then react with another halogen molecule to form the halogenated product. Understanding this stepwise process is essential for predicting the outcome of reactions starting from cyclohexane to bromocyclohexane.

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Textbook Question

Show how you would synthesize each compound, starting with alkenes or cycloalkenes that contain no more than six carbon atoms. You may use any additional reagents you need.

(a)