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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2:48 minutes

Problem 8

Textbook Question

Show how you would accomplish the following conversions.a. cis-hex-3-ene to meso-hexane-3,4-diol

Verified step by step guidance

Identify the functional groups in the starting material and the target molecule. The starting material is an alkene (cis-hex-3-ene), and the target molecule is a diol (meso-hexane-3,4-diol).

Recognize that the conversion involves the addition of hydroxyl groups (OH) across the double bond of the alkene. This is typically achieved through a syn-dihydroxylation reaction.

Select an appropriate reagent for syn-dihydroxylation. Osmium tetroxide (OsO4) followed by a reducing agent like sodium bisulfite (NaHSO3) or hydrogen peroxide (H2O2) is commonly used for this purpose.

Apply the syn-dihydroxylation reaction to the cis-hex-3-ene. The OsO4 will add across the double bond in a syn fashion, meaning both hydroxyl groups will add to the same side of the former double bond, preserving the stereochemistry.

Verify the stereochemistry of the product. Since the starting alkene is cis, the syn addition will result in a meso compound, which is a molecule with multiple stereocenters that is superimposable on its mirror image.

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Key Concepts

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

Cis-Trans Isomerism

Cis-trans isomerism refers to the different spatial arrangements of atoms in a molecule that has restricted rotation around a double bond. In the case of cis-hex-3-ene, the two substituents on the double bond are on the same side, which influences the molecule's reactivity and physical properties. Understanding this concept is crucial for predicting the outcomes of reactions involving alkenes.

Hydroxylation Reactions

Hydroxylation reactions involve the addition of hydroxyl (–OH) groups to a double bond, converting alkenes into alcohols. This transformation can be achieved through various methods, such as syn-dihydroxylation, where both hydroxyl groups are added to the same side of the double bond. Recognizing the mechanism of hydroxylation is essential for converting cis-hex-3-ene to meso-hexane-3,4-diol.

Meso Compounds

Meso compounds are achiral molecules that contain multiple stereocenters but possess an internal plane of symmetry. In the case of meso-hexane-3,4-diol, the presence of two hydroxyl groups on adjacent carbons creates stereocenters, yet the molecule remains superimposable on its mirror image. Understanding the concept of meso compounds is vital for recognizing the stereochemical outcome of the conversion from cis-hex-3-ene.

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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.

(c)