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

Dihydroxylation

Organic Chemistry

10. Addition Reactions

Dihydroxylation

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Problem 45f(v,vi)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA; (vi) 1. OsO₄ 2. NaHSO₃
(f)

Verified step by step guidance

Step 1: Analyze the given alkene structure. The molecule contains a double bond, which is the reactive site for the reactions described in the problem.

Step 2: For condition (v) mCPBA, understand that mCPBA (meta-chloroperoxybenzoic acid) is a reagent used for epoxidation of alkenes. This reaction converts the double bond into an epoxide (a three-membered cyclic ether). The stereochemistry of the epoxide will depend on the stereochemistry of the alkene.

Step 3: For condition (vi) 1. OsO₄ 2. NaHSO₃, recognize that this is a dihydroxylation reaction. Osmium tetroxide (OsO₄) adds two hydroxyl groups (-OH) to the double bond in a syn addition, meaning both hydroxyl groups will be added to the same face of the alkene. Sodium bisulfite (NaHSO₃) is used to quench the reaction and reduce OsO₄.

Step 4: Predict the product for condition (v). The double bond in the alkene will be converted into an epoxide. The stereochemistry of the epoxide will depend on the geometry of the starting alkene.

Step 5: Predict the product for condition (vi). The double bond in the alkene will be converted into a diol with syn stereochemistry, meaning the two hydroxyl groups will be added to the same side of the molecule.

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Key Concepts

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

Epoxidation

Epoxidation is a reaction where an alkene is converted into an epoxide, a three-membered cyclic ether. This transformation is typically achieved using reagents like mCPBA (meta-Chloroperbenzoic acid), which adds an oxygen atom across the double bond of the alkene. The resulting epoxide is a highly reactive intermediate that can undergo further reactions, such as ring-opening.

Dihydroxylation

Dihydroxylation refers to the addition of two hydroxyl (–OH) groups across a double bond in an alkene. This can be accomplished using reagents such as OsO₄ (osmium tetroxide) followed by a reducing agent like NaHSO₃ (sodium bisulfite). The process typically results in the formation of vicinal diols, where the hydroxyl groups are added to adjacent carbon atoms, leading to increased polarity and reactivity.

Stereochemistry of Reactions

Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In reactions involving alkenes, such as epoxidation and dihydroxylation, the stereochemical outcome is crucial. For instance, the addition of reagents can lead to syn or anti addition, influencing the configuration of the product and its subsequent reactivity and properties.

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Textbook Question

Predict the product of each of the following alcohol synthesis reactions.

(d)

Textbook Question

We have studied a number of pericyclic reactions previously. Draw the mechanism of the steps shown. The section number where this material was first studied is given for your review.

(d)

Textbook Question

Draw the structure of and name the enantiomeric diols that result from the cis-dihydroxylation of the alkene shown.

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA; (vi) 1. OsO₄ 2. NaHSO₃

(l)

Textbook Question

Which of molecules A–D would you expect to give a positive permanganate test? That is, which would result in a purple KMnO₄ solution turning brown?

(c)

Textbook Question

How might you make the catalytic cycle in Figure 9.31 more sustainable while still using NMO as the co-oxidant?

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Textbook Question

Using 1,2-dimethylcyclohexene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) If a chiral product is shown, assume that it is part of a racemic mixture.

(d)

Textbook Question

Show how you would synthesize each compound using methylenecyclohexane as your starting material.

(f)

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