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

Halohydrin

Organic Chemistry

10. Addition Reactions

Halohydrin

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Problem 9

Textbook Question

(••) Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iii) Br₂, H₂O(h)

Verified step by step guidance

Identify the type of reaction: The reaction of an alkene with Br₂ in the presence of H₂O is a halohydrin formation reaction.

Understand the mechanism: The reaction proceeds via the formation of a bromonium ion intermediate, which is then attacked by water.

Determine regioselectivity: The water molecule will attack the more substituted carbon of the bromonium ion, leading to Markovnikov addition.

Consider stereochemistry: The addition of Br and OH will be anti, meaning they will add to opposite sides of the double bond.

Predict the product: The final product will be a halohydrin, with a bromine atom and a hydroxyl group added across the double bond.

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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.

Bromohydrin Formation

Bromohydrin formation occurs when an alkene reacts with bromine in the presence of water. The bromonium ion intermediate is attacked by water, leading to the formation of a bromohydrin, which is a compound containing both a bromine atom and a hydroxyl group (-OH) on adjacent carbon atoms, resulting in a vicinal dibromide.

Regioselectivity

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple products are possible. In the reaction of alkenes with Br₂ and H₂O, the regioselectivity is influenced by the stability of the carbocation intermediates formed during the reaction, often leading to the more substituted alcohol being produced as the major product.

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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.

(a)

Textbook Question

Provide arrow-pushing mechanisms for Assessments 9.10(b) and 9.10(c) that rationalize the regioselective and stereospecific formation of each halohydrin.

(b)

(c)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iii) Br₂, H₂O

(d)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iv) Cl₂, CH₃OH

(d)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iv) Cl₂, CH₃OH

(h)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iii) Br₂, H₂O

(k)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iv) Cl₂, CH₃OH

(k)

Textbook Question

At the beginning of Chapter 9, we stated that after finishing Chapters 8 and 9, we would have the ability to make a large variety of functional groups using related reactions. Show the reagent(s) necessary to convert 1-isobutylcyclohexene into the following molecules.

(c)

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