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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2:59 minutes

Problem 13c

Textbook Question

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

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Analyze the structure of the halohydrin provided. The molecule contains a chlorine atom and a hydroxyl group (-OH) attached to adjacent carbons. This suggests that the halohydrin was formed via the addition of Cl₂ and H₂O to an alkene.

Identify the stereochemistry of the halohydrin. The chlorine atom is on a wedge (indicating it is coming out of the plane), and the hydroxyl group is on a dash (indicating it is going into the plane). This anti-addition stereochemistry is characteristic of halohydrin formation.

Determine the location of the double bond in the starting alkene. The double bond must be between the two carbons where the chlorine and hydroxyl groups are now attached. This is because halohydrin formation involves the electrophilic addition of Cl₂ and H₂O across the double bond.

Consider the structure of the alkene. The alkene must have a cyclopentyl group on one side and an isopropyl group on the other side of the double bond to match the substituents in the halohydrin product.

Propose the alkene structure. Based on the analysis, the alkene should be 1-cyclopentyl-1-isopropylethene, with the double bond positioned between the two carbons that now bear the chlorine and hydroxyl groups.

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Key Concepts

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

Alkenes

Alkenes are hydrocarbons that contain at least one carbon-carbon double bond (C=C). They are unsaturated compounds and can undergo various reactions, including addition reactions, where atoms or groups are added to the carbon atoms of the double bond. Understanding the structure and reactivity of alkenes is crucial for predicting the products of reactions, such as the formation of halohydrins.

Halohydrin Formation

Halohydrins are compounds formed when alkenes react with halogens and water, resulting in the addition of a halogen atom and a hydroxyl group (OH) across the double bond. This reaction typically occurs via a mechanism involving the formation of a cyclic halonium ion intermediate, which influences the regioselectivity and stereochemistry of the product. Recognizing the mechanism is essential for determining which alkene can yield the desired halohydrin.

Regioselectivity

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In the context of halohydrin formation, the regioselectivity is influenced by the stability of the carbocation intermediates formed during the reaction. Understanding regioselectivity helps in predicting which alkene will produce the desired halohydrin based on the substitution pattern of the alkene and the nature of the halogen.

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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

(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

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iii) Br₂, H₂O ; (iv) Cl₂, CH₃OH.

(e)

Textbook Question

Predict the product of the following haloalkane syntheses.

(e)

Textbook Question

Halohydrin formation is a stereospecific reaction. Identify the products of halohydrin formation of the following diastereomeric alkenes to demonstrate this stereospecificity.

Textbook Question

In light of your answer to Assessment 9.47, predict the product of the following reactions we have seen previously where an alcohol is substituted for water.

(c)

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

Key Concepts

Alkenes

Halohydrin Formation

Regioselectivity

Watch next

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