Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 19m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 18m
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 Acids3h 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

28. Carbohydrates

Epimerization

Organic Chemistry

28. Carbohydrates

Epimerization

Previous problemNext problem

2:51 minutes

Problem 20-5dBruice - 8th Edition

Textbook Question

d. What sugar is the C-4 epimer of d-lyxose?

Verified step by step guidance

Identify the structure of D-lyxose, which is an aldopentose with the configuration (2R, 3S, 4R).

Understand that an epimer is a diastereomer that differs in configuration at only one stereogenic center.

Focus on the C-4 carbon of D-lyxose, as the problem asks for the C-4 epimer.

Invert the configuration at the C-4 carbon of D-lyxose from R to S, while keeping the rest of the molecule the same.

Determine the name of the sugar with the new configuration, which will be the C-4 epimer of D-lyxose.

Recommended similar problem, with video answer:

Verified Solution

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.

Epimers

Epimers are a specific type of diastereomer that differ in configuration at only one stereogenic center. In the context of sugars, this means that two sugars can have the same molecular formula and differ only at one carbon atom's stereochemistry. Understanding epimers is crucial for identifying relationships between different sugars, such as d-lyxose and its epimer.

D-lyxose Structure

D-lyxose is a five-carbon aldose sugar with a specific arrangement of hydroxyl groups around its carbon atoms. The configuration of these hydroxyl groups determines its properties and reactivity. Knowing the structure of d-lyxose is essential for determining its epimer, as one must identify the correct carbon atom (C-4) to change its configuration.

Sugar Nomenclature

Sugar nomenclature involves the systematic naming of carbohydrates based on their structure and stereochemistry. The prefix 'D-' indicates the configuration of the sugar relative to glyceraldehyde, while the suffix denotes the number of carbon atoms. Familiarity with this nomenclature is important for accurately identifying and comparing sugars, such as recognizing the C-4 epimer of d-lyxose.