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

10. Addition Reactions

Halogenation

Organic Chemistry

10. Addition Reactions

Halogenation

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6:01 minutes

Problem 65b

Textbook Question

Identify A through O:

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Step 1: Analyze the starting material. The given compound is a cyclohexene ring with a methyl group attached to one of the carbons in the ring. The double bond is located between two carbons in the ring.

Step 2: Identify the reagent and reaction type. Bromine (Br₂) is used, which typically reacts with alkenes via an electrophilic addition mechanism. This reaction involves the addition of bromine across the double bond.

Step 3: Predict the intermediate. The double bond in the cyclohexene ring will react with Br₂, forming a bromonium ion intermediate. This intermediate is a three-membered ring structure where bromine is bonded to both carbons of the former double bond.

Step 4: Determine the final products. The bromonium ion is attacked by a bromide ion (Br⁻), leading to the formation of a dibromo product. The bromine atoms will add anti to each other (on opposite sides of the ring) due to the stereochemistry of the reaction.

Step 5: Assign labels A and B. A represents the major product, which is the dibromo compound formed from the addition of bromine across the double bond. B represents the bromide ion (Br⁻) that is released during the reaction.

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Key Concepts

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

Halogenation

Halogenation is a chemical reaction that involves the addition of halogens, such as bromine (Br2), to an organic compound. In this process, the halogen atoms replace hydrogen atoms in alkenes or react with other functional groups, leading to the formation of haloalkanes or other halogenated compounds. Understanding this reaction is crucial for predicting the products formed in the given reaction.

Mechanism of Electrophilic Addition

The mechanism of electrophilic addition describes how electrophiles, like Br2, react with nucleophilic sites in alkenes or cycloalkenes. The reaction typically proceeds through the formation of a cyclic bromonium ion intermediate, which is then attacked by a nucleophile, leading to the formation of the final products. This concept is essential for understanding how compounds A and B are generated from the starting material.

Stereochemistry of Products

Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In halogenation reactions, the formation of products can lead to stereoisomers, such as enantiomers or diastereomers, depending on the configuration of the reactants and the reaction conditions. Recognizing the stereochemical implications is important for identifying the specific structures of compounds A and B.

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Related Practice

Textbook Question

Predict the product(s) of each of the following reactions, making sure to indicate the relative stereochemical outcome. Indicate any racemic mixtures by drawing both enantiomers.

(f)

Textbook Question

In which of the two steps in the alkene halogenation mechanism does a redox reaction occur?

Textbook Question

Bromination of a highly electron-rich alkene such as 2-methoxybut-2-ene has been shown to produce approximately equal mixtures of the trans- and cis-dibromide. Suggest an explanation for this observation.

Textbook Question

In Chapter 19, we discuss the reaction of enols with bromine. This reaction produces α -bromoketones in good yields. Suggest a mechanism for this reaction and justify its deviation from the dibromide product you might have expected.

Textbook Question

Predict the product of the following addition reactions to dienes.

(c)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (i) Br₂ (ii) Cl₂.

(e)

Textbook Question

Provide an arrow-pushing mechanism that rationalizes the stereospecific formation of each dihalide in Assessment 9.6.

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (i) Br₂ (ii) Cl₂

(f)

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