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

Previous problemNext problem

Problem 45h(vii)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vii) 1. mCPBA 2. H₂SO₄, H₂O
(h)

Verified step by step guidance

Step 1: Recognize the reaction type. The problem involves a two-step reaction sequence. The first step uses mCPBA (meta-chloroperoxybenzoic acid), which is a reagent commonly used for epoxidation of alkenes. This means the double bond in the alkene will be converted into an epoxide (a three-membered cyclic ether).

Step 2: Draw the structure of the starting alkene and identify the position of the double bond. This is important because the epoxidation will occur specifically at the double bond, forming a three-membered ring with an oxygen atom.

Step 3: Apply the stereochemistry of the reaction. mCPBA reacts with alkenes in a syn addition manner, meaning the oxygen atom is added to the same face of the double bond. If the alkene is cis, the epoxide will also be cis. If the alkene is trans, the epoxide will be trans.

Step 4: Consider the second step of the reaction. Since the second step is not fully specified in the problem (indicated by '2. (h)'), you would need to clarify what reagent or condition 'h' refers to. Commonly, epoxides can undergo ring-opening reactions under acidic or basic conditions, leading to different products depending on the nucleophile and the reaction environment.

Step 5: Predict the final product(s) based on the second step. If 'h' refers to a specific reagent or condition, determine how it interacts with the epoxide. For example, under acidic conditions, the epoxide ring opens at the more substituted carbon, while under basic conditions, it opens at the less substituted carbon. Draw the possible product(s) accordingly.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Play a video:

Was this helpful?

Key Concepts

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

Alkenes

Alkenes are hydrocarbons that contain at least one carbon-carbon double bond (C=C). They are unsaturated compounds, meaning they have fewer hydrogen atoms than alkanes. The presence of the double bond makes alkenes reactive, allowing them to undergo various addition reactions, including those with oxidizing agents like mCPBA.

mCPBA (meta-Chloroperbenzoic Acid)

mCPBA is a peracid commonly used in organic chemistry for the epoxidation of alkenes. It introduces an oxygen atom across the double bond, forming an epoxide, which is a three-membered cyclic ether. This reaction is stereospecific and can lead to different products depending on the configuration of the starting alkene.

Epoxidation

Epoxidation is a chemical reaction that converts alkenes into epoxides through the addition of an oxygen atom. This reaction is significant because epoxides are highly reactive intermediates that can undergo further transformations, such as ring-opening reactions, leading to various functional groups. Understanding the mechanism of epoxidation is crucial for predicting the products of reactions involving alkenes and oxidizing agents.

Watch next

Master General properties of epoxidation. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

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.

a. cis-hex-2-ene

b. trans-hex-2-ene

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA

(d)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA;

(h)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA;

(k)

Textbook Question

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

(a)

Textbook Question

When producing a chiral molecule, epoxide formation still results in a mixture of enantiomers, despite its stereospecificity.

(b) How is it that a reaction can be stereospecific while still producing two enantiomers?

Textbook Question

Rank the reactivity of the following alkenes with mCPBA ( 1 = most reactive , 5 least reactive ).

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vii) 1. mCPBA 2. H2SO4, H2O(h)

Key Concepts

Alkenes

mCPBA (meta-Chloroperbenzoic Acid)

Epoxidation

Watch next

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vii) 1. mCPBA 2. H₂SO₄, H₂O
(h)