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 45h(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
(h)

Verified step by step guidance

Step 1: Recognize the reaction type. The reagents OsO₄ (osmium tetroxide) followed by NaHSO₃ (sodium bisulfite) indicate a dihydroxylation reaction. This reaction adds two hydroxyl (-OH) groups to the alkene in a syn addition manner.

Step 2: Identify the structure of the alkene. Analyze the given alkene structure to determine the position of the double bond, as this is where the reaction will occur.

Step 3: Understand the mechanism. OsO₄ reacts with the alkene to form a cyclic osmate ester intermediate. This intermediate ensures that the two hydroxyl groups will be added to the same face of the double bond (syn addition).

Step 4: Perform the second step of the reaction. The NaHSO₃ is used to cleave the osmate ester intermediate, releasing the diol (a molecule with two hydroxyl groups) as the final product.

Step 5: Predict the stereochemistry of the product. Since the reaction proceeds via syn addition, the two hydroxyl groups will be on the same side of the former double bond. Draw the product(s) considering the stereochemistry and any possible enantiomers if the starting alkene is not symmetrical.

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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 the presence of 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 alcohol functional groups on adjacent carbon atoms. 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, NaHSO₃ serves to quench the reaction and can help in isolating the diol product by forming a stable bisulfite adduct. This step is essential for ensuring that the desired product is obtained in a pure form, free from excess reagents.

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Related Practice

Textbook Question

Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate.

(j)

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

(k)

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?

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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(h)

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
(h)