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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Problem 45k(i)

Textbook Question

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

Verified step by step guidance

Step 1: Recognize the type of reaction. The reaction involves an alkene reacting with bromine (Br₂). This is a halogenation reaction, specifically the addition of bromine across the double bond of the alkene.

Step 2: Understand the mechanism. Bromine reacts with the alkene via an electrophilic addition mechanism. The π-electrons of the alkene double bond attack the bromine molecule, forming a bromonium ion intermediate.

Step 3: Analyze the stereochemistry. The bromonium ion intermediate is cyclic and prevents free rotation. Bromine ions (Br⁻) will attack the more accessible side of the bromonium ion, leading to anti-addition (the two bromine atoms will add to opposite sides of the double bond).

Step 4: Predict the product. The final product will be a vicinal dibromide, where two bromine atoms are added to adjacent carbons of the original double bond. If the alkene is symmetrical, only one product will form. If the alkene is asymmetrical, consider regioselectivity and stereochemistry to determine the possible products.

Step 5: Verify the structure. Draw the structure of the product(s) based on the anti-addition mechanism and confirm that the bromine atoms are added to the correct carbons with the appropriate stereochemistry.

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Key Concepts

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

Electrophilic Addition

Electrophilic addition is a fundamental reaction mechanism in organic chemistry where an electrophile reacts with a nucleophile, typically involving alkenes. In the case of alkenes reacting with Br₂, the double bond acts as a nucleophile, attacking the electrophilic bromine molecule, leading to the formation of a cyclic bromonium ion intermediate.

Bromination of Alkenes

Bromination is a specific type of electrophilic addition where bromine (Br₂) adds across the double bond of an alkene. This reaction results in the formation of vicinal dibromides, where bromine atoms are added to adjacent carbon atoms. The stereochemistry of the product can vary, leading to both anti and syn addition products.

Stereochemistry

Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the bromination of alkenes, the formation of a bromonium ion intermediate leads to the possibility of anti-addition, resulting in products that can exhibit different stereochemical configurations, such as enantiomers or diastereomers.

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Related Practice

Textbook Question

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

(d)

Textbook Question

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

(d)

Textbook Question

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

(h)

Textbook Question

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

(h)

Textbook Question

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

(k)

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.

(b)

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?

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