Table of contents

1. A Review of General Chemistry(0)
2. Molecular Representations(0)
3. Acids and Bases(0)
4. Alkanes and Cycloalkanes(0)
5. Chirality(0)
6. Thermodynamics and Kinetics(0)
7. Substitution Reactions(0)
8. Elimination Reactions(0)
9. Alkenes and Alkynes(0)
10. Addition Reactions(0)
11. Radical Reactions(0)
12. Alcohols, Ethers, Epoxides and Thiols(0)
13. Alcohols and Carbonyl Compounds(0)
14. Synthetic Techniques(0)
15. Analytical Techniques:IR, NMR, Mass Spect(0)
16. Conjugated Systems(0)
17. Ultraviolet Spectroscopy(0)
18. Aromaticity(0)
19. Reactions of Aromatics: EAS and Beyond(0)
20. Phenols(0)
21. Aldehydes and Ketones: Nucleophilic Addition(0)
22. Carboxylic Acid Derivatives: NAS(0)
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides(0)
24. Enolate Chemistry: Reactions at the Alpha-Carbon(0)
25. Condensation Chemistry(0)
26. Amines(0)
27. Heterocycles(0)
28. Carbohydrates(0)
29. Amino Acids(0)
30. Peptides and Proteins(0)
31. Catalysis in Organic Reactions(0)
32. Lipids (0)
33. The Organic Chemistry of Metabolic Pathways(0)
34. Nucleic Acids(0)
35. Transition Metals(0)
36. Synthetic Polymers(0)

28. Carbohydrates

Monosaccharides - Wohl Degradation

28. Carbohydrates

Monosaccharides - Wohl Degradation: Videos & Practice Problems

Video Lessons Practice Worksheet

Monosaccharides - Wohl Degradation Practice Problems

20 problems

1PRACTICE PROBLEM

Provide a suitable mechanism to show the elimination of the cyano group (last step) in the following Wohl degradation reaction.

Wohl degradation mechanism showing D-Mannose conversion to D-Arabinose.

rank

2PRACTICE PROBLEM

Identify the two monosaccharides that will form D-xylose via Wohl degradation.

3PRACTICE PROBLEM

Give the two monosaccharides that will form D-lyxose when they undergo Wohl degradation.

4PRACTICE PROBLEM

An optically inactive alditol forms when aldose X undergoes reduction with sodium borohydride. When X undergoes Wohl degradation, Y is formed which converts to an optically active alditol. When Y undergoes Wohl degradation, D-threose is formed. Determine the identity of X and Y.

5PRACTICE PROBLEM

Kiliani–Fischer synthesis of (+)-glyceraldehyde was performed three times to get a hexose. Determine the identity of the hexose based on the following experimental data:

(i) an optically inactive aldaric acid is formed by oxidation of the hexose with nitric acid

(ii) an optically active aldaric acid is formed when the hexose undergoes Wohl degradation followed by nitric acid oxidation

(iii) and D-threose is formed by a second Wohl degradation

6PRACTICE PROBLEM

What is the primary purpose of Wohl degradation in carbohydrate chemistry?

7PRACTICE PROBLEM

What role do cyanohydrins play in Wohl degradation?

8PRACTICE PROBLEM

Why does Wohl degradation result in a single epimer product?

9PRACTICE PROBLEM

During Wohl degradation, why is the formation of an oxime a crucial step in transforming D-glucose?

10PRACTICE PROBLEM

What is the function of the Beckman rearrangement in the context of Wohl degradation?

11PRACTICE PROBLEM

How does methoxide facilitate the elimination of cyanohydrin in Wohl degradation?

12PRACTICE PROBLEM

Which type of elimination is primarily involved in Wohl degradation, and how does it differ from beta elimination?

13PRACTICE PROBLEM

Why is the stereochemistry of chiral centers retained during Wohl degradation?

14PRACTICE PROBLEM

If L-glucose undergoes Wohl degradation, what product is expected?

15PRACTICE PROBLEM

How can Wohl degradation be used to synthesize D-ribose from D-glucose?

16PRACTICE PROBLEM

Which reaction can be considered the opposite of Wohl degradation?

17PRACTICE PROBLEM

What intermediate is formed when D-glucose is transformed into an amine derivative during Wohl degradation?

18PRACTICE PROBLEM

How is C2 stereochemistry lost during Wohl degradation, resulting in a single epimer product?

19PRACTICE PROBLEM

During Wohl degradation, what specific molecular transformation occurs in the Beckman rearrangement step?

20PRACTICE PROBLEM

What is the result of using methoxide in the elimination step of Wohl degradation?

Previous Topic: Monosaccharides - Kiliani-Fischer Next Topic: Monosaccharides - Ruff Degradation

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap