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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2:00 minutes

Problem 20c

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.
(c)

Verified step by step guidance

Step 1: Recognize the reaction type. The reagents OsO₄ (osmium tetroxide) followed by NaHSO₃ and H₂O indicate a dihydroxylation reaction. This reaction adds two hydroxyl (-OH) groups to the double bond in a syn addition manner.

Step 2: Identify the structure of the starting material. The starting material is a bicyclic compound with a double bond in one of the rings. The double bond is the site of the reaction.

Step 3: Predict the stereochemical outcome. Osmium tetroxide adds hydroxyl groups to the same face of the double bond (syn addition). This means the two -OH groups will be added to the same side of the plane of the double bond.

Step 4: Draw the product. The double bond will be replaced by two hydroxyl groups (-OH) on the same face of the ring system. Since the molecule is symmetric, the product will not have enantiomers but will be a single stereoisomer.

Step 5: Confirm the reaction mechanism. The reaction proceeds through the formation of an osmate ester intermediate, which is then cleaved by NaHSO₃ and H₂O to yield the diol product.

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Key Concepts

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

Dihydroxylation

Dihydroxylation is a chemical reaction that involves the addition of two hydroxyl (–OH) groups to a double bond in an alkene. This reaction can be achieved through various methods, including the use of osmium tetroxide (OsO4), which forms a cyclic osmate ester intermediate. The subsequent hydrolysis of this intermediate leads to the formation of vicinal diols, which are compounds with hydroxyl groups on adjacent carbon atoms.

Stereochemistry

Stereochemistry refers to the study of the spatial arrangement of atoms in molecules and how this arrangement affects their chemical behavior. In reactions like dihydroxylation, the stereochemical outcome is crucial, as the addition of hydroxyl groups can lead to the formation of chiral centers, resulting in enantiomers. Understanding stereochemistry helps predict the relative configurations of the products, such as whether they are enantiomers or diastereomers.

Racemic Mixtures

A racemic mixture is a 1:1 mixture of two enantiomers, which are molecules that are mirror images of each other but cannot be superimposed. In the context of dihydroxylation, if the reaction leads to the formation of a chiral product without a preference for one enantiomer over the other, a racemic mixture will be produced. This is important in organic synthesis, as the presence of both enantiomers can affect the biological activity and properties of the compound.

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Related Practice

Textbook Question

Synthesize the following molecules beginning with only organic molecules containing three carbons or fewer.

(f)

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.]

(a)

Textbook Question

Show how you would accomplish the following conversions.

c. trans-hex-3-ene to meso-hexane-3,4-diol

Textbook Question

Predict the major products of the following reactions, including stereochemistry where appropriate.

(k) cyclopentanol + H₂SO₄/heat

(l) product from (k) + OsO₄/H₂O₂, then HIO₄

(m) sodium ethoxide + 1-bromobutane

Multiple Choice

Predict the major organic product of the following reaction.

Multiple Choice