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

Previous problemNext problem

2:42 minutes

Problem 8

Textbook Question

Show how you would accomplish the following conversions.d. trans-hex-3-ene to (d,l)-hexane-3,4-diol

Verified step by step guidance

Step 1: Begin with the trans-hex-3-ene molecule. Recognize that you need to add hydroxyl groups (OH) to the 3rd and 4th carbon atoms to form a diol.

Step 2: Perform an epoxidation reaction on trans-hex-3-ene. Use a peroxyacid, such as mCPBA (meta-chloroperoxybenzoic acid), to convert the alkene into an epoxide. This will form an epoxide ring between the 3rd and 4th carbon atoms.

Step 3: Open the epoxide ring to form the diol. Use an acidic or basic hydrolysis method. For example, you can use aqueous acid (H3O+) or a base like NaOH followed by water to open the epoxide ring, resulting in the formation of (d,l)-hexane-3,4-diol.

Step 4: Ensure that the reaction conditions are controlled to favor the formation of the (d,l) mixture, which indicates the formation of both enantiomers (diastereomers) of the diol.

Step 5: Verify the stereochemistry of the product to confirm that you have obtained the (d,l)-hexane-3,4-diol, which is a racemic mixture of the two enantiomers.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Alkenes and Their Reactions

Alkenes are hydrocarbons that contain at least one carbon-carbon double bond. They are reactive compounds that can undergo various reactions, such as hydrogenation, hydrohalogenation, and hydration. Understanding the reactivity of alkenes is crucial for converting trans-hex-3-ene into other functional groups, as these reactions will dictate the pathway to the desired product.

Stereochemistry

Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the conversion of trans-hex-3-ene to (d,l)-hexane-3,4-diol, it is important to consider the stereochemical configuration of the reactants and products. The presence of chiral centers in the diol product means that understanding stereoisomerism is essential for predicting the outcome of the reaction.

Diol Formation

Diols, or glycols, are compounds containing two hydroxyl (-OH) groups. The conversion of alkenes to diols typically involves syn or anti-dihydroxylation reactions, where water or other nucleophiles add across the double bond. In this case, the transformation of trans-hex-3-ene to (d,l)-hexane-3,4-diol will require specific reagents and conditions to ensure the correct addition of hydroxyl groups to achieve the desired product.

Watch next

Master General properties of syn vicinal dihydroxylation. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

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

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)

Multiple Choice

Predict the major organic product of the following reaction.

Multiple Choice

Which of the following reactions will yield a meso product?

Textbook Question

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

Textbook Question

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

(i)

Textbook Question

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