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

Previous problemNext problem

3:11 minutes

Problem 1

Textbook Question

Write the initiation, propagation, and termination steps for the monochlorination of cyclohexane.

Verified step by step guidance

Write the initiation step: In this step, the chlorine molecule (Cl₂) undergoes homolytic cleavage under the influence of UV light or heat to form two chlorine radicals. Represent this as: Cl₂ → 2Cl•.

Write the first propagation step: A chlorine radical (Cl•) reacts with cyclohexane (C₆H₁₂), abstracting a hydrogen atom to form hydrogen chloride (HCl) and a cyclohexyl radical (C₆H₁₁•). Represent this as: Cl• + C₆H₁₂ → HCl + C₆H₁₁•.

Write the second propagation step: The cyclohexyl radical (C₆H₁₁•) reacts with another chlorine molecule (Cl₂), forming chlorocyclohexane (C₆H₁₁Cl) and regenerating a chlorine radical (Cl•). Represent this as: C₆H₁₁• + Cl₂ → C₆H₁₁Cl + Cl•.

Write the termination steps: Termination occurs when two radicals combine to form a stable molecule. Examples include: (1) Cl• + Cl• → Cl₂, (2) C₆H₁₁• + Cl• → C₆H₁₁Cl, and (3) C₆H₁₁• + C₆H₁₁• → C₆H₁₁-C₆H₁₁.

Ensure the overall reaction is balanced: Combine the initiation, propagation, and termination steps to confirm that the overall reaction is the substitution of one hydrogen atom in cyclohexane with a chlorine atom, forming chlorocyclohexane and HCl.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

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 alkanes react with halogens to form alkyl halides. This process involves the generation of free radicals, which are highly reactive species with unpaired electrons. The reaction typically occurs in three stages: initiation, propagation, and termination, each playing a crucial role in the overall mechanism.

Initiation Step

The initiation step involves the formation of free radicals from halogen molecules, usually through the application of heat or light. For monochlorination of cyclohexane, chlorine molecules (Cl2) dissociate into two chlorine radicals (Cl•), which are essential for starting the reaction. This step is critical as it sets the stage for the subsequent propagation steps.

Propagation and Termination Steps

Propagation steps involve the reaction of the generated radicals with cyclohexane, leading to the formation of new radicals and the desired product, chlorocyclohexane. This cycle continues until the radicals are consumed. The termination step occurs when two radicals combine to form a stable molecule, effectively stopping the reaction. Understanding these steps is vital for predicting the products and yields of the reaction.

Watch next

Master The one reaction that alkanes will actually undergo. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

What alkyl halide will be obtained in greatest yield? Ignore stereoisomers.

Textbook Question

What hydrocarbon with molecular formula C₄H₁₀ forms only two monochlorinated products? Both products are achiral.

Textbook Question

What hydrocarbon with the same molecular formula as in part a forms three monochlorinated products? One is achiral and two are chiral.

Textbook Question

Explain why iodine (I₂) does not react with ethane, even though I₂ is more easily cleaved homolytically than the other halogens.

Textbook Question

Provide an arrow-pushing mechanism for the following alkane bromination. [Don't forget to use fishhook arrows to represent the movement of single electrons.]

Textbook Question

If a small amount of a moderately nonpolar poisonous compound was added to a pond, why would it be safer to drink the water than it would be to eat the fish that live there?

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)

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap