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

Epoxidation

Organic Chemistry

10. Addition Reactions

Epoxidation

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2:54 minutes

Problem 58f

Textbook Question

What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?
f. MCPBA (a peroxyacid)

Verified step by step guidance

Identify the type of reaction: MCPBA (meta-chloroperoxybenzoic acid) is a peroxyacid commonly used to perform epoxidation of alkenes. This reaction involves the addition of an oxygen atom across the double bond to form an epoxide (a three-membered cyclic ether).

Analyze the structure of the starting material: 2-methyl-2-butene is an alkene with a double bond between the second and third carbons, and a methyl group attached to the second carbon. The double bond is the reactive site for the epoxidation reaction.

Understand the regioselectivity and stereoselectivity: Epoxidation with MCPBA is a concerted reaction, meaning the oxygen atom is added to the double bond in a single step. The reaction is stereospecific, preserving the stereochemistry of the alkene. Since 2-methyl-2-butene is not stereochemically complex (no cis/trans isomers), this step is straightforward.

Draw the product: The oxygen atom from MCPBA will form a three-membered ring (epoxide) with the two carbons of the double bond. The methyl group on the second carbon remains in place, and the overall structure becomes a substituted epoxide.

Verify the major product: Since MCPBA reacts with the double bond in a predictable manner and there are no competing reactions, the major product will be the epoxide derived from 2-methyl-2-butene. Ensure the structure is drawn correctly, showing the three-membered ring and the methyl substituent.

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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 various electrophiles, leading to the formation of more stable carbocations and ultimately the major product of the reaction.

Peroxyacids and Epoxidation

Peroxyacids, such as MCPBA, are strong oxidizing agents that can convert alkenes into epoxides through a process called epoxidation. This reaction involves the formation of a three-membered cyclic ether, which is a key intermediate that can lead to various products depending on subsequent reactions.

Regioselectivity and Stereochemistry

Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others, while stereochemistry deals with the spatial arrangement of atoms in molecules. In the reaction of 2-methyl-2-butene with MCPBA, understanding these concepts helps predict the major product and its configuration, as the formation of the epoxide can lead to different stereoisomers.

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Related Practice

Textbook Question

Predict the product(s) of each of the following reactions, making sure to indicate the relative stereochemical outcome. Indicate any racemic mixtures by drawing both enantiomers.

(a)

Textbook Question

Predict the product(s) of each of the following reactions, making sure to indicate the relative stereochemical outcome. Indicate any racemic mixtures by drawing both enantiomers.

(c)

Multiple Choice

Predict the major organic product of the following reaction.

Textbook Question

Draw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed.

3. a peroxyacid

Textbook Question

Calculate the atom economy for the reactions shown. In each, what happens to the percentage of material that is not incorporated into the major product?

Textbook Question

Predict the major products of the following reactions.

a. cis-hex-2-ene + mCPBA in chloroform

Textbook Question

Predict the products, including stereochemistry where appropriate, for the m-chloroperoxybenzoic acid epoxidations of the following alkenes.

c. cis-cyclodecene

d. trans-cyclodecene

Textbook Question

Predict the products, including stereochemistry where appropriate, for the m-chloroperoxybenzoic acid epoxidations of the following alkenes.