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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4:32 minutes

Problem 45h(i)

Textbook Question

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

Verified step by step guidance

Step 1: Recognize the type of reaction. The reaction involves an alkene and bromine (Br₂), which is a halogenation reaction. This reaction typically proceeds via an electrophilic addition mechanism.

Step 2: Understand the mechanism. When Br₂ reacts with an alkene, the π-electrons of the double bond attack one of the bromine atoms, forming a cyclic bromonium ion intermediate. This intermediate is positively charged and highly reactive.

Step 3: Determine the nucleophilic attack. The bromide ion (Br⁻), which is generated when Br₂ splits, attacks the more substituted carbon of the bromonium ion (if applicable, based on Markovnikov's rule). This results in the anti-addition of bromine atoms across the double bond.

Step 4: Predict the stereochemistry. Since the bromonium ion intermediate is cyclic, the attack by the bromide ion occurs from the opposite side of the ring, leading to anti-addition. This means the two bromine atoms will be added to opposite faces of the former double bond.

Step 5: Draw the product(s). The final product will be a vicinal dibromide (two bromine atoms attached to adjacent carbons). If the starting alkene is symmetrical, a single product will form. If the alkene is asymmetrical, consider the possibility of stereoisomers (e.g., enantiomers or diastereomers).

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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 typically 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 of Addition Reactions

Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the bromination of alkenes, the addition of bromine can lead to different stereoisomers, such as enantiomers or diastereomers, depending on whether the addition occurs from the same or opposite sides of the double bond, influencing the final product's configuration.

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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.

(c)

Textbook Question

What is the major product of each of the following reactions, assuming that one equivalent of each reagent is used in each reaction?

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: (ii) Cl₂

(h)

Textbook Question

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

(k)

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)

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

Key Concepts

Electrophilic Addition

Bromination of Alkenes

Stereochemistry of Addition Reactions

Watch next

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