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

Epoxide Reactions

Organic Chemistry

10. Addition Reactions

Epoxide Reactions

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5:23 minutes

Problem 33a,b

Textbook Question

What stereoisomers are obtained from the reaction of the alkenes in [PROBLEM 10-32] with a peroxyacid followed by reaction with hydroxide ion?
a. trans-2-butene
b. cis-2-butene

Verified step by step guidance

Identify the reaction type: The reaction involves the conversion of an alkene into an epoxide using a peroxyacid (e.g., mCPBA) followed by a ring-opening reaction with hydroxide ion. This is a two-step reaction mechanism.

Step 1: Epoxidation of the alkene. The peroxyacid reacts with the alkene to form an epoxide. The stereochemistry of the epoxide depends on the stereochemistry of the starting alkene. If the alkene is cis, the epoxide will also be cis (retention of stereochemistry). If the alkene is trans, the epoxide will be trans.

Step 2: Ring-opening of the epoxide. The hydroxide ion attacks the less sterically hindered carbon of the epoxide in an SN2 mechanism. This results in inversion of configuration at the carbon being attacked, leading to the formation of a diol.

Analyze the stereochemistry of the products: Depending on the stereochemistry of the starting alkene (cis or trans), the diol products will have different stereochemical relationships (e.g., enantiomers or diastereomers). For example, a cis-alkene will yield a meso diol, while a trans-alkene will yield a pair of enantiomers.

Summarize the stereoisomers: Based on the stereochemistry of the starting alkene, determine whether the products are enantiomers, diastereomers, or a meso compound. Ensure to consider all possible stereoisomers formed during the reaction.

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Key Concepts

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

Stereoisomerism

Stereoisomerism refers to the phenomenon where compounds have the same molecular formula and connectivity of atoms but differ in the spatial arrangement of those atoms. This can lead to different physical and chemical properties. In organic chemistry, stereoisomers include enantiomers and diastereomers, which are crucial for understanding the outcomes of reactions involving chiral centers.

Epoxidation

Epoxidation is a chemical reaction that converts alkenes into epoxides, which are three-membered cyclic ethers. This reaction is typically facilitated by peroxyacids, such as m-chloroperbenzoic acid (MCPBA). The formation of epoxides introduces a reactive functional group that can undergo further reactions, influencing the stereochemistry of the resulting products.

Nucleophilic Ring Opening

Nucleophilic ring opening is a reaction where a nucleophile attacks an electrophilic carbon in a strained cyclic compound, such as an epoxide. This process often leads to the formation of diols and can result in the generation of stereoisomers depending on the stereochemistry of the starting material and the conditions of the reaction. The presence of hydroxide ion as a nucleophile is common in this context.

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Related Practice

Textbook Question

The existence of the NIH shift was established by determining the major product obtained from rearrangement of the following arene oxide, in which a hydrogen has been replaced by a deuterium.

b. What would be the major product if the carbocation forms phenol by losing H⁺ or D⁺, rather than by going through the NIH shift?

Textbook Question

Which of the following reactions occurs more rapidly?

Textbook Question

What products are obtained from the reaction of cyclohexene oxide with

b. methylamine?

Textbook Question

b. A small amount of a product containing a six-membered ring is also formed. Draw the structure of that product.

c. Why is so little six-membered ring product formed?

Textbook Question

What stereoisomers are obtained from the reaction of the alkenes in [PROBLEM 10-32] with a peroxyacid followed by reaction with hydroxide ion?

c. cis-2-pentene

d. trans-2-pentene

Textbook Question

Three arene oxides can be obtained from phenanthrene.

c. If a phenanthrene oxide can lead to the formation of more than one phenol, which phenol will be obtained in greater yield?

Textbook Question

Cellosolve® is the trade name for 2-ethoxyethanol, a common industrial solvent. This compound is produced in chemical plants that use ethylene as their only organic feedstock. Show how you would accomplish this industrial process.

Textbook Question

Show the rest of the mechanism for formation of the cyclized intermediate in Figure 14-6.

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What stereoisomers are obtained from the reaction of the alkenes in [PROBLEM 10-32] with a peroxyacid ­followed by reaction with hydroxide ion?a. trans-2-buteneb. cis-2-butene

Key Concepts

Stereoisomerism

Epoxidation

Nucleophilic Ring Opening

Watch next

What stereoisomers are obtained from the reaction of the alkenes in [PROBLEM 10-32] with a peroxyacid followed by reaction with hydroxide ion?
a. trans-2-butene
b. cis-2-butene