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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2:54 minutes

Problem 45k(vi)

Textbook Question

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

Verified step by step guidance

Identify the reaction type: The reagents OsO₄ (osmium tetroxide) followed by NaHSO₃ (sodium bisulfite) indicate a syn-dihydroxylation reaction. This reaction adds two hydroxyl (-OH) groups to the double bond of the alkene in a syn (same side) fashion.

Analyze the structure of the alkene: Determine the position of the double bond in the given alkene. The double bond is the site of reactivity where the hydroxyl groups will be added.

Understand the mechanism: OsO₄ reacts with the alkene to form a cyclic osmate ester intermediate. This intermediate ensures that the two hydroxyl groups are added to the same face of the double bond (syn addition).

Perform the second step: The cyclic osmate ester is then cleaved by NaHSO₃, which reduces the osmium and releases the diol (a molecule with two hydroxyl groups).

Predict the product: The final product will be a vicinal diol (two hydroxyl groups on adjacent carbons) with both hydroxyl groups added to the same side of the original double bond. Ensure stereochemistry is considered if the alkene is asymmetric.

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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 characterized by at least one carbon-carbon double bond. Their reactivity is primarily due to this double bond, which can undergo various addition reactions. Understanding how alkenes react with different reagents is crucial for predicting the products of these reactions.

Osmium Tetroxide (OsO₄) Reaction

Osmium tetroxide is a powerful oxidizing agent used in organic chemistry to convert alkenes into vicinal diols (glycols) through syn-dihydroxylation. This reaction involves the addition of hydroxyl groups (–OH) across the double bond, resulting in a compound with two adjacent alcohol groups. The stereochemistry of the product is important, as it retains the configuration of the starting alkene.

Sodium Bisulfite (NaHSO₃) Workup

Sodium bisulfite is often used in organic reactions as a reducing agent and for the purification of reaction products. In the context of the OsO₄ reaction, the NaHSO₃ workup helps to quench excess osmium and can also facilitate the isolation of the diol product. This step is essential for ensuring that the reaction is complete and that the desired product is obtained in a pure form.

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Related Practice

Textbook Question

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

(b)

Textbook Question

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

(d)

Textbook Question

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

(d)

Textbook Question

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

(h)

Textbook Question

At the beginning of Chapter 9, we stated that after finishing Chapters 8 and 9, we would have the ability to make a large variety of functional groups using related reactions. Show the reagent(s) necessary to convert 1-isobutylcyclohexene into the following molecules.

(b)

Textbook Question

(d)

Textbook Question

The concertedness of the OsO₄ reaction results in both oxygens being added to the same face of the molecule (i.e., syn addition). How might these conditions be modified in order to prepare a trans-diol?

Textbook Question

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

(b)

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

Key Concepts

Alkene Reactivity

Osmium Tetroxide (OsO₄) Reaction

Sodium Bisulfite (NaHSO₃) Workup

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