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

Problem 20Bruice - 8th Edition

Textbook Question

Name the epimers of d-glucose.

Verified step by step guidance

Understand that epimers are stereoisomers that differ in configuration at only one stereogenic center.

Recall that D-glucose is an aldohexose with the chemical formula C6H12O6 and has four chiral centers.

Identify the chiral centers in D-glucose, which are at carbon atoms C2, C3, C4, and C5.

Determine the epimers of D-glucose by changing the configuration at each of these chiral centers one at a time, while keeping the others the same.

Recognize that the most common epimers of D-glucose are D-mannose (epimer at C2) and D-galactose (epimer at C4).

Recommended similar problem, with video answer:

Verified Solution

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

Video duration:

0m:0s

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 carbohydrates, epimers are sugars that have the same molecular formula but differ in the arrangement of atoms around one specific carbon atom. Understanding epimers is crucial for distinguishing between different forms of sugars, such as glucose and its derivatives.

D-Glucose Structure

D-Glucose is a six-carbon aldose sugar with the molecular formula C6H12O6. It has multiple stereocenters, specifically at carbons 2, 3, 4, and 5. The configuration of these stereocenters determines the specific form of glucose and its epimers, making it essential to know the structure of D-glucose to identify its epimers accurately.

Common Epimers of D-Glucose

The most notable epimers of D-glucose are D-mannose and D-galactose. D-mannose differs from D-glucose at the C2 carbon, while D-galactose differs at the C4 carbon. Recognizing these epimers is important in biochemistry and nutrition, as they can have different biological roles and properties despite their similar structures.