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

Previous problemNext problem

6:43 minutes

Problem 81b

Textbook Question

What is the major product of each of the following reactions?
b.

Verified step by step guidance

Analyze the structure of the given molecule. It contains a hydroxyl group (-OH) and a double bond (alkene) in the chain. The reaction involves bromine (Br₂) in CH₂Cl₂, which is a typical reagent for electrophilic addition to alkenes.

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

Determine the regioselectivity and stereoselectivity of the reaction. Bromine adds across the double bond in an anti-addition manner, meaning the two bromine atoms will be added to opposite sides of the double bond.

Identify the major product. The bromine atoms will add to the carbons of the double bond, resulting in a vicinal dibromide. The hydroxyl group (-OH) does not participate in this reaction and remains unchanged.

Draw the final structure of the major product. The double bond is replaced by two bromine atoms attached to the carbons that were part of the double bond, and the stereochemistry reflects anti-addition.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Halohydrin Formation

Halohydrin formation is a reaction where alkenes react with halogens (like Br2) in the presence of water or alcohols to form halohydrins. This process involves the electrophilic addition of the halogen to the double bond, followed by the nucleophilic attack of water or alcohol on the more substituted carbon, leading to the formation of a halohydrin product.

Regioselectivity

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In the case of halohydrin formation, the regioselectivity is influenced by the stability of the carbocation intermediate formed during the reaction, favoring the more substituted carbon atom for the nucleophilic attack.

Solvent Effects

The choice of solvent can significantly influence the outcome of a chemical reaction. In this case, CH2Cl2 (dichloromethane) is a non-polar solvent that can stabilize the halogen and facilitate the reaction without participating in it. The solvent's properties can affect the reaction rate and the regioselectivity of the halohydrin formation.

Watch next

Master General properties of halohydrin formation. with a bite sized video explanation from Johnny

Start learning