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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Problem 41(2)

Textbook Question

a. What alkene is required to synthesize each of the following compounds?
b. What other epoxide is formed in each synthesis?
c. Assign an R or S configuration to each asymmetric center.
2.

Verified step by step guidance

Step 1: Analyze the given epoxide structure. The molecule contains an oxygen atom in a three-membered ring (epoxide) attached to two asymmetric centers. The substituents on the asymmetric centers are CH3CH2 (ethyl group) and CH2CH2CH3 (propyl group).

Step 2: To synthesize this epoxide, identify the alkene precursor. Epoxides are typically formed via the reaction of alkenes with peroxy acids (e.g., mCPBA). The alkene precursor should have the same substituents as the epoxide but without the oxygen atom. In this case, the alkene would be CH3CH=CHCH2CH2CH3.

Step 3: Determine the stereochemistry of the epoxide formation. Epoxidation of alkenes can lead to the formation of two stereoisomers (cis and trans epoxides). The stereochemistry of the alkene precursor will dictate the stereochemistry of the epoxide. If the alkene is cis, the epoxide will be cis; if the alkene is trans, the epoxide will be trans.

Step 4: Identify the other epoxide that could be formed. Since the reaction can produce stereoisomers, the other epoxide would have the opposite stereochemistry at the asymmetric centers. For example, if the given epoxide is (R,R), the other epoxide would be (S,S).

Step 5: Assign R or S configuration to each asymmetric center. Use the Cahn-Ingold-Prelog priority rules to assign the configuration. For each asymmetric center, prioritize the substituents based on atomic number and connectivity, then determine the direction of rotation (clockwise for R, counterclockwise for S).

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Key Concepts

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

Alkene Reactivity

Alkenes are unsaturated hydrocarbons that contain at least one carbon-carbon double bond. Their reactivity is primarily due to this double bond, which can undergo various reactions such as electrophilic addition, oxidation, and polymerization. Understanding the specific alkene required for a synthesis involves recognizing how the double bond can be manipulated to form desired products.

Epoxide Formation

Epoxides are cyclic ethers with a three-membered ring structure that includes an oxygen atom. They are typically formed through the reaction of alkenes with peracids or halohydrins. In the context of synthesis, identifying the epoxide formed is crucial as it can serve as an intermediate in further reactions, influencing the final product's structure and properties.

Stereochemistry and R/S Configuration

Stereochemistry refers to the spatial arrangement of atoms in molecules and is essential for understanding the properties and reactivity of chiral compounds. The R/S system is a method for assigning configurations to chiral centers based on the Cahn-Ingold-Prelog priority rules. Accurately assigning R or S configurations is vital for predicting the behavior of molecules in reactions and their interactions with biological systems.

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Related Practice

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.

(d)

Textbook Question

Evidence for the concertedness of epoxide formation comes from the stereospecificity of the reaction. If step 2 of a hypothetical stepwise mechanism were slow enough to make the reaction non-concerted, how would the product distribution change?

Textbook Question

What alkene would you treat with a peroxyacid in order to obtain each of the epoxides in Problem 27?

a. 2-propyloxirane

b. cyclohexene oxide

Textbook Question

a. What alkene is required to synthesize each of the following compounds?

b. What other epoxide is formed in each synthesis?

c. Assign an R or S configuration to each asymmetric center.

Textbook Question

What alkene would you treat with a peroxyacid in order to obtain each of the epoxides in Problem 27?

c. 2,2,3,3-tetramethyloxirane

d. 2,3-epoxy-2-methylpentane

Textbook Question

Magnesium monoperoxyphthalate (MMPP) epoxidizes alkenes much like mCPBA. MMPP is more stable, however, and it may be safer to use for large-scale and industrial reactions. Propose a mechanism for the reaction of trans-2-methylhept-3-ene with MMPP, and predict the structure of the product(s).

Textbook Question

Limonene is one of the compounds that give lemons their tangy odor. Show the structures of the products expected when limonene reacts with an excess of each of these reagents.

b. m-chloroperoxybenzoic acid

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)

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a. What alkene is required to synthesize each of the following compounds?b. What other epoxide is formed in each synthesis?c. Assign an R or S configuration to each asymmetric center.2.

Key Concepts

Alkene Reactivity

Epoxide Formation

Stereochemistry and R/S Configuration

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a. What alkene is required to synthesize each of the following compounds?
b. What other epoxide is formed in each synthesis?
c. Assign an R or S configuration to each asymmetric center.
2.