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

Free Radical Halogenation

Organic Chemistry

11. Radical Reactions

Free Radical Halogenation

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7:39 minutes

Problem 14

Textbook Question

Provide a mechanism for the chlorination of cyclohexane. Be sure to include initiation, propagation, and three possible termination steps.

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Initiation: The chlorination of cyclohexane begins with the homolytic cleavage of the chlorine molecule (Cl₂) under the influence of heat or light. This results in the formation of two chlorine radicals. The reaction can be represented as: Cl₂ → 2Cl•.

Propagation Step 1: A chlorine radical abstracts a hydrogen atom from cyclohexane, forming hydrochloric acid (HCl) and a cyclohexyl radical. This step can be represented as: Cl• + C₆H₁₂ → HCl + C₆H₁₁•.

Propagation Step 2: The cyclohexyl radical reacts with another chlorine molecule to form chlorocyclohexane and regenerate a chlorine radical. This step can be represented as: C₆H₁₁• + Cl₂ → C₆H₁₁Cl + Cl•.

Termination Step 1: Two chlorine radicals can combine to form chlorine gas, effectively removing radicals from the reaction mixture. This step can be represented as: Cl• + Cl• → Cl₂.

Termination Step 2: A cyclohexyl radical can combine with a chlorine radical to form chlorocyclohexane, terminating the radical chain. This step can be represented as: C₆H₁₁• + Cl• → C₆H₁₁Cl.

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Key Concepts

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

Free Radical Halogenation

Free radical halogenation is a reaction mechanism where halogens, such as chlorine, react with alkanes to form alkyl halides. This process involves the generation of free radicals, which are highly reactive species with unpaired electrons. The mechanism consists of three main stages: initiation, propagation, and termination, each playing a crucial role in the overall reaction.

Initiation Step

The initiation step involves the formation of free radicals, typically through the homolytic cleavage of a chlorine molecule (Cl2) under heat or light. This generates two chlorine radicals, which are essential for starting the chlorination process. The presence of these radicals sets the stage for the subsequent propagation steps, where they will react with cyclohexane.

Propagation and Termination Steps

Propagation steps involve the reaction of chlorine radicals with cyclohexane to form alkyl radicals, which can further react with chlorine molecules to produce alkyl halides and regenerate chlorine radicals. Termination steps occur when two radicals combine to form a stable product, effectively stopping the chain reaction. These steps are crucial for controlling the reaction and determining the final products.

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Related Practice

Textbook Question

Predict the major monohalogenation product(s) of the following reactions. Indicate whether you think the reaction will be selective and justify your position.

(c)

Textbook Question

Predict the product(s) of the following halogenation reactions. Only one equivalent of the halogen is used in each case. If the reaction proceeds selectively, indicate this by only drawing the major product. If the reaction is not selective, draw all possible products.

(e)

Textbook Question

(f)

Textbook Question

We have studied the following reactions in previous chapters. For each, (i) indicate which reaction sheets they should appear on, (ii) show the best structure to use to represent them, and (iii) write the notes you could put in the margin so that the mechanism is implied.

(b) Radical halogenation of an alkane

Textbook Question

For the following reaction, answer questions (a)–(d).

(a) Give an arrow-pushing mechanism, including the initiation step and two propagation steps.

Textbook Question

Predict the major products of the following alkane halogenation reactions. [The number of products shown ignores the formation of racemic mixtures.]

(c)

Textbook Question

Other molecules can be used as initiators in radical reactions. One such molecule is 2, 2'-azobisisobutyronitrile (AIBN). Show an arrow-pushing mechanism that rationalizes the formation of the following radical species. What are the driving forces of this reaction?

Textbook Question

Cyclizations can be carried out under radical conditions involving Bu₃SnH and a catalytic amount of AIBN. Suggest a mechanism for this reaction. [Pay close attention to the bonds formed and broken in developing your mechanism. It may be helpful to number the carbons.]

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