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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2:21 minutes

Problem 58j

Textbook Question

What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?
j. Br₂/CH₃OH

Verified step by step guidance

Identify the type of reaction: The reaction involves 2-methyl-2-butene (an alkene) reacting with bromine (Br₂) in the presence of methanol (CH₃OH). This is an electrophilic addition reaction where the alkene undergoes halogenation in the presence of a nucleophile (methanol).

Understand the mechanism: The π-electrons of the double bond in 2-methyl-2-butene attack one of the bromine atoms in Br₂, forming a bromonium ion intermediate. This intermediate is a three-membered ring with a positive charge on the bromine atom.

Determine the role of methanol: Methanol (CH₃OH) acts as a nucleophile in this reaction. It will attack the more substituted carbon of the bromonium ion (due to Markovnikov's rule and the stability of the carbocation-like transition state).

Predict the product: The methanol adds to the more substituted carbon, while the bromine atom from the bromonium ion remains attached to the less substituted carbon. This results in the formation of a bromomethoxy product.

Consider stereochemistry: Since the bromonium ion intermediate is cyclic, the attack by methanol occurs from the opposite side (anti-addition). This leads to a product with anti stereochemistry, where the bromine and methoxy groups are on opposite sides of the molecule.

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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 electrophiles to alkenes, where the double bond acts as a nucleophile. In the case of 2-methyl-2-butene, the double bond can react with electrophiles like Br2, leading to the formation of a bromonium ion intermediate. This intermediate can then be attacked by nucleophiles, such as methanol (CH3OH), resulting in the formation of a product with both bromine and methoxy groups.

Regioselectivity

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In the reaction of 2-methyl-2-butene with Br2 and CH3OH, the regioselectivity will determine which carbon atom of the alkene will bond with the bromine and which will bond with the methanol, leading to the major product. Understanding the stability of intermediates helps predict the favored pathway.

Stereochemistry

Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the reaction of 2-methyl-2-butene with Br2 and CH3OH, the formation of a bromonium ion can lead to different stereochemical outcomes depending on how the nucleophile attacks the intermediate. This can result in the formation of different stereoisomers, which is crucial for determining the final product's structure.

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Related Practice

Textbook Question

1-Methylcyclohexene forms two products when it reacts with bromine in methanol.

a. Draw the mechanism for the formation of the products.

b. Describe their stereochemical relationship—that is, are they enantiomers or diastereomers?

Textbook Question

Using any alkene and any other reagents, how would you prepare the following compounds?

Textbook Question

What will be the major product obtained from the reaction of Br₂ with 1-butene if the reaction is carried out in

a. dichloromethane?

b. water?

Textbook Question

Each of the following reactions has two nucleophiles that could add to the intermediate formed by the reaction of the alkene with an electrophile. What is the major product of each reaction?

Textbook Question

A graduate student attempted to form the iodohydrin of the alkene shown below. Her analysis of the products showed a good yield of an unexpected product. Propose a mechanism to explain the formation of this product.

Textbook Question

Using 1,2-dimethylcyclohexene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) If a chiral product is shown, assume that it is part of a racemic mixture.

(g)

Textbook Question

Show how you would synthesize each compound using methylenecyclohexane as your starting material.

(h)

Textbook Question

The solutions to Solved Problem 8-5 showed only how one enantiomer of the product is formed. For each product, show how an equally probable reaction forms the other enantiomer.

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What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?j. Br2/CH3OH

Key Concepts

Electrophilic Addition Reactions

Regioselectivity

Stereochemistry

Watch next

What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?
j. Br₂/CH₃OH