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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3:02 minutes

Problem 45k(iv)

Textbook Question

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

Verified step by step guidance

Identify the type of reaction: The reaction involves an alkene reacting with Cl₂ in the presence of CH₃OH. This is an example of a halohydrin formation reaction, where the alkene undergoes electrophilic addition.

Understand the mechanism: The reaction begins with the alkene attacking Cl₂, forming a cyclic chloronium ion intermediate. This intermediate is highly reactive and will be attacked by a nucleophile.

Determine the nucleophile: In this reaction, CH₃OH (methanol) acts as the nucleophile. Methanol will attack the more substituted carbon of the cyclic chloronium ion due to the stability of the resulting carbocation-like transition state.

Add the nucleophile: The methanol (CH₃OH) adds to the more substituted carbon, while the chlorine (Cl⁻) ends up on the less substituted carbon. This results in a halohydrin product, where one carbon has a chlorine atom and the other has a methoxy group (-OCH₃).

Consider stereochemistry: The addition of Cl₂ and CH₃OH to the alkene is anti-addition, meaning the chlorine and the methoxy group will be added to opposite faces of the alkene. This should be reflected in the stereochemistry of the product(s).

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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 this process, the double bond of the alkene acts as a nucleophile, attacking the electrophile, leading to the formation of a more stable product. This mechanism is crucial for understanding how alkenes react with halogens and other electrophiles.

Halogenation

Halogenation refers to the addition of halogen atoms (like Cl₂) to an alkene, resulting in the formation of vicinal dihalides. This reaction typically proceeds through a cyclic halonium ion intermediate, which influences the stereochemistry of the product. Understanding halogenation is essential for predicting the products when alkenes react with halogens in various solvents.

Solvent Effects

The choice of solvent can significantly influence the outcome of a chemical reaction. In the case of Cl₂ reacting with alkenes in methanol (CH₃OH), the solvent can participate in the reaction, leading to the formation of chloromethanol products instead of simple dihalides. Recognizing the role of solvents helps in predicting the specific products formed in reactions involving alkenes and halogens.

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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: (iv) Cl₂, CH₃OH

(d)

Textbook Question

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

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

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)

Textbook Question

When alkenes react with bromine in water, a halohydrin is produced. When water is replaced with methanol in this reaction, a different product is produced. Suggest a mechanism for the formation of this product.

Textbook Question

Explain why water attacks the carbon of the bromonium ion as opposed to the bromonium ion itself in the second step of halohydrin formation.

Textbook Question

Suggest an alkene that could be used to make each of the following halohydrins.

(c)

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