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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6:40 minutes

Problem 70a(3)

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

Verified step by step guidance

Understand the reaction: The reaction of an alkene with a peroxyacid (RCO₃H) results in the formation of an epoxide. This is an electrophilic addition reaction where the π-bond of the alkene reacts with the peroxyacid to form a three-membered cyclic ether (epoxide).

Analyze the starting materials: cis-2-butene and trans-2-butene are geometric isomers of 2-butene. Cis-2-butene has both methyl groups on the same side of the double bond, while trans-2-butene has the methyl groups on opposite sides of the double bond.

Predict the stereochemistry of the products: The stereochemistry of the starting alkene determines the stereochemistry of the epoxide. For cis-2-butene, the epoxide will be a cis-epoxide (both substituents on the same side of the ring). For trans-2-butene, the epoxide will be a trans-epoxide (substituents on opposite sides of the ring).

Draw the products: For cis-2-butene, draw a three-membered epoxide ring with both methyl groups on the same side. For trans-2-butene, draw a three-membered epoxide ring with the methyl groups on opposite sides. Ensure the stereochemistry is clearly indicated using wedge and dash bonds.

Verify stereoisomers: Since the products are epoxides, they can exist as stereoisomers. For cis-2-butene, the product will be a single stereoisomer (cis-epoxide). For trans-2-butene, the product will also be a single stereoisomer (trans-epoxide).

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Key Concepts

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

Alkenes and Stereochemistry

Alkenes are hydrocarbons that contain at least one carbon-carbon double bond. The stereochemistry of alkenes, such as cis and trans isomers, is crucial in determining the products of reactions. In this case, cis-2-butene has substituents on the same side of the double bond, while trans-2-butene has them on opposite sides, leading to different reactivity and product formation.

Peroxyacid Reactions

Peroxyacids, such as m-chloroperbenzoic acid (MCPBA), are strong oxidizing agents that can react with alkenes to form epoxides. This reaction involves the addition of an oxygen atom across the double bond, resulting in a three-membered cyclic ether. Understanding this mechanism is essential for predicting the products formed from the reaction of alkenes with peroxyacids.

Stereoisomerism in Epoxides

Epoxides can exhibit stereoisomerism due to the presence of chiral centers formed during their synthesis. When alkenes like cis-2-butene and trans-2-butene react with a peroxyacid, the resulting epoxide can exist in different stereoisomeric forms. It is important to identify and represent these stereoisomers to fully describe the products of the reaction.

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Related Practice

Textbook Question

Retrosynthetic analysis is the process of working backward to develop the synthesis of a new compound. In Chapter 10, we begin developing multistep syntheses in this manner. For now, try to work backward a single step by suggesting an alkene and a reagent that would give products (a)–(i). [Your answers should not include alkenes that undergo rearrangement to give the desired products.]

(f)

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

What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?

f. MCPBA (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