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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5:49 minutes

Problem 46e

Textbook Question

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

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 specifically targets allylic positions in the molecule.

Step 2: Identify the allylic positions in the given molecule. The allylic position is the carbon atom adjacent to the double bond. In this case, the allylic positions are the carbons directly connected to the double bond in the cyclohexene ring.

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 an allylic radical. This radical is stabilized by resonance.

Step 4: Draw the resonance structures of the allylic radical. The radical can delocalize over the π-system of the double bond, creating multiple resonance structures. These resonance structures indicate the possible sites for bromine addition.

Step 5: Add bromine to the allylic radical. Bromine will attach to the allylic position, forming the brominated product. Include all possible stereoisomers if the allylic position is chiral or if multiple resonance structures lead to different products.

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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 or alkane, 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 form the brominated product.

Radical Mechanism

A radical mechanism involves the formation and reaction of free radicals, which are species with unpaired electrons. In the context of allylic bromination, the reaction starts with the generation of radicals through the homolytic cleavage of the N–Br bond in NBS, followed by the abstraction of hydrogen from the allylic position, leading to the formation of a new carbon-bromine bond.

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 possibility of forming different configurations at the chiral centers created during the reaction, necessitating the consideration of all possible stereoisomers in the final product.

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

Key Concepts

Allylic Bromination

Radical Mechanism

Stereoisomerism

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