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

Allylic Bromination

Organic Chemistry

11. Radical Reactions

Allylic Bromination

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5:23 minutes

Problem 46f

Textbook Question

Draw the products of the following reactions, including all stereoisomers:
f.

Verified step by step guidance

Step 1: Recognize the reaction type. The reaction involves NBS (N-Bromosuccinimide) in the presence of heat (Δ) and peroxide. This is a radical bromination reaction that selectively brominates allylic positions due to the stability of the allylic radical.

Step 2: Identify the allylic position in the given molecule. The allylic position is the carbon atom adjacent to the double bond. In this case, the allylic position is the carbon atom directly connected to the double bond in the side chain.

Step 3: Generate the allylic radical intermediate. The peroxide initiates the formation of a bromine radical, which abstracts a hydrogen atom from the allylic position, forming a stable allylic radical.

Step 4: Add the bromine atom to the allylic radical. The bromine radical reacts with the allylic radical to form the brominated product at the allylic position.

Step 5: Consider stereoisomers. Since the allylic position is not a stereocenter in this molecule, no stereoisomers are formed. The product will be a single brominated compound at the allylic position.

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Key Concepts

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

Allylic Bromination

Allylic bromination is a reaction where bromine is added to the allylic position of an alkene, typically using N-bromosuccinimide (NBS) in the presence of a peroxide. This reaction proceeds via a radical mechanism, where the allylic hydrogen is abstracted, forming a resonance-stabilized radical that can then react with bromine to yield brominated products.

Radical Mechanism

A radical mechanism involves the formation and reaction of free radicals, which are highly reactive species with unpaired electrons. In the context of allylic bromination, the reaction starts with the generation of a radical intermediate through the homolytic cleavage of a bond, allowing for subsequent reactions that lead to the formation of products, including stereoisomers.

Stereoisomerism

Stereoisomerism refers to the existence of compounds with the same molecular formula and connectivity but different spatial arrangements of atoms. In the case of allylic bromination, the formation of stereoisomers occurs due to the different orientations of substituents around the double bond, leading to distinct products that must be accounted for when drawing the final reaction products.

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Draw the products of the following reactions, including all stereoisomers: f.

Key Concepts

Allylic Bromination

Radical Mechanism

Stereoisomerism

Watch next

Draw the products of the following reactions, including all stereoisomers:
f.