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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4:04 minutes

Problem 50

Textbook Question

Identify the two different alkenes that undergo allylic halogenation to prepare the compound shown.

Verified step by step guidance

Step 1: Understand the concept of allylic halogenation. Allylic halogenation involves the substitution of a hydrogen atom at the allylic position (the carbon atom adjacent to a double bond) with a halogen atom, typically using reagents like N-bromosuccinimide (NBS) in the presence of light or heat.

Step 2: Analyze the structure of the target compound. Identify the location of the halogen atom and the allylic position relative to the double bond in the compound.

Step 3: Determine the possible alkenes that could lead to the target compound through allylic halogenation. Consider the position of the double bond and the allylic carbon that would be halogenated.

Step 4: Draw the structures of the potential alkenes. Ensure that each alkene has a double bond in a position that allows for allylic halogenation to produce the target compound.

Step 5: Verify the structures by considering the mechanism of allylic halogenation. Ensure that the halogenation of each proposed alkene leads to the formation of the target compound, taking into account the stability of the allylic radical intermediates.

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Key Concepts

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

Allylic Halogenation

Allylic halogenation is a reaction where a halogen is introduced at the allylic position of an alkene, which is the carbon atom adjacent to the double bond. This reaction typically involves the use of N-bromosuccinimide (NBS) in the presence of light or heat, facilitating the formation of a radical intermediate that leads to the substitution of a hydrogen atom with a halogen.

Alkene Structure

Alkenes are hydrocarbons containing at least one carbon-carbon double bond, characterized by the general formula CnH2n. The structure of an alkene influences its reactivity and the position of the double bond determines the possible sites for allylic substitution. Understanding the structure is crucial for identifying potential alkenes that can undergo allylic halogenation to form a specific compound.

Radical Mechanism

Radical mechanisms involve species with unpaired electrons, which are highly reactive. In allylic halogenation, radicals are generated by the homolytic cleavage of bonds, often initiated by light or heat. These radicals facilitate the substitution process by abstracting hydrogen atoms from the allylic position, allowing halogens to attach and form the desired product.

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Related Practice

Textbook Question

Using 1,2-dimethylcyclohexene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) If a chiral product is shown, assume that it is part of a racemic mixture.

(a)