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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2:20 minutes

Problem 22c

Textbook Question

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

Verified step by step guidance

Identify the type of reaction: This is a free radical halogenation reaction involving chlorine (Cl₂) and heat, which typically leads to the substitution of hydrogen atoms in alkanes with chlorine atoms.

Analyze the structure of the alkane: The given alkane is 2-methylbutane, which has primary, secondary, and tertiary hydrogen atoms available for substitution.

Determine the reactivity of hydrogen atoms: In free radical halogenation, tertiary hydrogens are the most reactive, followed by secondary, and then primary hydrogens. This is due to the stability of the resulting free radicals.

Predict the major products: The reaction will likely produce three different chlorinated products based on the substitution at different hydrogen sites. Consider the formation of products from the substitution at tertiary, secondary, and primary positions.

Consider the number of products: Since the problem specifies three products, focus on the most likely sites for chlorine substitution that would lead to distinct products, ignoring any racemic mixtures that might form.

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Key Concepts

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

Alkane Halogenation

Alkane halogenation is a substitution reaction where an alkane reacts with a halogen (like Cl2 or Br2) to form alkyl halides. This process typically involves the generation of free radicals through the homolytic cleavage of the halogen bond, followed by a series of radical propagation steps that lead to the substitution of hydrogen atoms in the alkane with halogen atoms.

Free Radical Mechanism

The free radical mechanism is a multi-step process that includes initiation, propagation, and termination steps. In the initiation step, halogen molecules dissociate into free radicals. During propagation, these radicals react with alkanes to form new radicals and alkyl halides. The process continues until termination occurs, where two radicals combine to form a stable product, effectively ending the reaction.

Regioselectivity

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple products are possible. In alkane halogenation, the formation of products is influenced by the stability of the resulting radicals; more stable tertiary radicals are favored over primary ones, leading to a higher yield of products derived from more substituted carbon centers.

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Related Practice

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.

(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

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

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

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.]

Textbook Question

What alkane, with molecular formula C₅H₁₂, forms only one monochlorinated product when it is heated with Cl₂?

Textbook Question

Explain why the rate of bromination of methane decreases if HBr is added to the reaction mixture.

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

Key Concepts

Alkane Halogenation

Free Radical Mechanism

Regioselectivity

Watch next

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