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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Problem 62c

Textbook Question

A halogenation intended to make compound A formed B instead.

(c) Given the two mechanisms you drew, why might B have formed selectively?

Verified step by step guidance

Step 1: Begin by reviewing the mechanisms you have drawn for the halogenation reactions of compound A. Ensure you understand the pathway for both the intended product (compound A) and the actual product (compound B).

Step 2: Consider the stability of the intermediates formed in each mechanism. Often, the formation of a more stable intermediate can lead to the selective formation of a particular product. Compare the stability of intermediates in the pathways leading to compounds A and B.

Step 3: Analyze the regioselectivity and stereoselectivity of the reaction. These factors can influence which product is formed preferentially. Look for any steric or electronic effects that might favor the formation of compound B over compound A.

Step 4: Evaluate the reaction conditions, such as temperature, solvent, and concentration of reagents. These can affect the rate and selectivity of the reaction, potentially favoring the formation of compound B.

Step 5: Consider any kinetic versus thermodynamic control in the reaction. Sometimes, the product formed is the result of kinetic control (faster formation) rather than thermodynamic control (more stable product). Determine if this is the case for compound B.

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Key Concepts

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

Halogenation Reaction

Halogenation is a chemical reaction that involves the addition of halogens to a compound, typically an alkane or alkene. This process can occur via radical or electrophilic mechanisms, depending on the substrate and conditions. Understanding the specific mechanism is crucial for predicting the product formed during halogenation.

Reaction Mechanism

A reaction mechanism outlines the step-by-step sequence of elementary reactions by which overall chemical change occurs. It includes the formation and breaking of bonds, intermediates, and transition states. Analyzing mechanisms helps in understanding why certain products are favored over others, as seen in the selective formation of compound B.

Selectivity in Chemical Reactions

Selectivity refers to the preference of a chemical reaction to yield one product over others. Factors influencing selectivity include steric effects, electronic effects, and the stability of intermediates. In the context of halogenation, selectivity might arise from the stability of the radical or carbocation intermediates formed during the reaction.

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Related Practice

Textbook Question

Suggest a mechanism for the following reactions.

(a)

Textbook Question

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

(b) Which is the weakest bond in molecule A?

Textbook Question

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

(d) Given your choice in (b), why is it the weakest bond?

Textbook Question

A halogenation intended to make compound A formed B instead.

(a) Suggest a mechanism for the intended formation of A.

Textbook Question

In the following reaction, which C―H bond would be most likely to react with a bromine radical?

Textbook Question

Tributyltin hydride (Bu₃SnH) is often used as a 'radical carrier' in radical reactions. Which bond would you expect to be weaker, Sn–H or C–H? How might this relate to radical stability? Explain your answer.

Textbook Question

Haloalkanes can be reduced to alkanes using radical reactions 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.]

Textbook Question

What are the product(s) of each of the following reactions? Disregard stereoisomers.

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A halogenation intended to make compound A formed B instead. (c) Given the two mechanisms you drew, why might B have formed selectively?

Key Concepts

Halogenation Reaction

Reaction Mechanism

Selectivity in Chemical Reactions

Watch next

A halogenation intended to make compound A formed B instead.

(c) Given the two mechanisms you drew, why might B have formed selectively?