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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3:42 minutes

Problem 16a

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)

Verified step by step guidance

Understand the reagent: mCPBA (meta-chloroperoxybenzoic acid) is a peracid commonly used for epoxidation of alkenes. It adds an oxygen atom across the double bond to form an epoxide (a three-membered cyclic ether).

Analyze the substrate: Identify the alkene in the given molecule. The double bond is the reactive site where mCPBA will act to form the epoxide.

Determine the stereochemical outcome: The epoxidation reaction with mCPBA is stereospecific. If the alkene is cis (Z-configuration), the epoxide will retain the cis stereochemistry. If the alkene is trans (E-configuration), the epoxide will retain the trans stereochemistry.

Account for chirality: If the alkene is part of a chiral molecule or generates a chiral center upon epoxidation, consider the possibility of forming enantiomers. If the starting material is achiral, the product will be a racemic mixture of enantiomers.

Draw the product(s): Represent the epoxide product(s) with the correct stereochemistry. If a racemic mixture is formed, draw both enantiomers explicitly to indicate the outcome.

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Key Concepts

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

mCPBA and its Role in Organic Reactions

mCPBA, or meta-chloroperbenzoic acid, 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. Understanding how mCPBA reacts with different substrates is crucial for predicting the products of these reactions.

Stereochemistry and Epoxide Formation

Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. When mCPBA reacts with alkenes, the stereochemical outcome of the epoxide can lead to different configurations (cis or trans) based on the starting alkene's geometry. Recognizing how stereochemistry influences the formation of products is essential for predicting the relative stereochemical outcomes.

Enantiomers and Racemic Mixtures

Enantiomers are pairs of molecules that are non-superimposable mirror images of each other, often resulting from chiral centers in a compound. When a reaction produces both enantiomers in equal amounts, it is termed a racemic mixture. Identifying and representing racemic mixtures is important in organic synthesis, especially when discussing the stereochemical outcomes of reactions involving chiral products.

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Related Practice

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: (vii) 1. mCPBA 2. H₂SO₄, H₂O

(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

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 ).

Textbook Question

One way to think about concerted reactions is to imagine them as being stepwise reactions where, besides the slowest step, all others have infinitesimally small activation energies. Considering the hypothetical stepwise mechanism and actual concerted mechanism of epoxide formation, show what a reaction coordinate diagram might look like for each possibility.

(a) Stepwise, hypothetical mechanism:

Textbook Question

(b) Concerted , actual mechanism (butterfly transition state:

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