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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4:47 minutes

Problem 66b

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the structure of the reactant. The molecule is a substituted cyclohexene with a double bond. The reaction involves bromine (Br₂) in methanol (CH₃OH), which suggests a bromination reaction in the presence of a nucleophile (methanol).

Step 2: Understand the mechanism. Bromine reacts with the double bond via electrophilic addition. The π-electrons of the double bond attack Br₂, forming a bromonium ion intermediate.

Step 3: Consider the role of methanol. Methanol acts as a nucleophile and will attack the more substituted carbon of the bromonium ion due to steric and electronic factors, leading to regioselectivity.

Step 4: Predict the stereochemistry. The attack by methanol occurs from the opposite side of the bromonium ion (anti-addition), resulting in a trans product.

Step 5: Draw the major product. The major product will have a bromine atom and a methoxy group (-OCH₃) added across the double bond in an anti configuration, with the methoxy group on the more substituted carbon.

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Key Concepts

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

Electrophilic Addition Reactions

Electrophilic addition reactions involve the addition of an electrophile to a nucleophile, typically across a double bond. In the case of alkenes, such as cyclohexene, the π bond acts as a nucleophile, reacting with electrophiles like Br2. This reaction leads to the formation of a more stable product, often resulting in the addition of halogens across the double bond.

Regioselectivity

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In the bromination of cyclohexene, the regioselectivity is influenced by the stability of the carbocation intermediates formed during the reaction. Understanding which carbon atoms are more favorable for electrophilic attack is crucial for predicting the major product.

Solvent Effects

The choice of solvent can significantly influence the outcome of a chemical reaction. In this case, methanol (CH3OH) serves as a polar protic solvent, which can stabilize charged intermediates and facilitate the reaction. The solvent can also participate in the reaction, potentially leading to the formation of products that include methanol-derived groups, such as methoxy groups, in the final product.

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