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

Monosaccharides - Strong Oxidation (Aldaric Acid)

Organic Chemistry

28. Carbohydrates

Monosaccharides - Strong Oxidation (Aldaric Acid)

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4:25 minutes

Problem 20bBruice - 8th Edition

Textbook Question

c. Name another pair of aldohexoses that are oxidized to identical aldaric acids.

Verified step by step guidance

Identify the structure of aldohexoses, which are monosaccharides containing six carbon atoms and an aldehyde group.

Understand that aldaric acids are formed by the oxidation of both the aldehyde group and the primary alcohol group of aldohexoses to carboxylic acids.

Recognize that aldohexoses differing only in the configuration of their chiral centers (excluding the carbonyl carbon and the primary alcohol carbon) will yield the same aldaric acid upon oxidation, as the terminal carbons are converted to the same functional group (carboxylic acid).

Consider aldohexoses like glucose and mannose, which differ only in the configuration at C2, but upon oxidation to aldaric acid, this difference becomes irrelevant as both the aldehyde group at C1 and the primary alcohol group at C6 are oxidized to carboxylic acids.

Conclude that any pair of aldohexoses that are epimers (differ at only one chiral center other than the first and last carbon) will be oxidized to identical aldaric acids.

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Key Concepts

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

Aldohexoses

Aldohexoses are six-carbon sugars that contain an aldehyde group. They are a subclass of monosaccharides and include common sugars like glucose and galactose. The presence of the aldehyde functional group at one end of the molecule is crucial for their reactivity and classification as aldoses.

Oxidation of Sugars

Oxidation of sugars involves the conversion of alcohol groups in the sugar molecule to carbonyl groups, resulting in the formation of acids. In the case of aldohexoses, the aldehyde group can be oxidized to a carboxylic acid, leading to the formation of aldaric acids. This process is significant in carbohydrate chemistry and can affect the properties and reactivity of the sugars.

Aldaric Acids

Aldaric acids are dicarboxylic acids derived from the oxidation of both the aldehyde and the primary alcohol groups of aldohexoses. They have two carboxylic acid functional groups, one at each end of the carbon chain. Identifying pairs of aldohexoses that yield the same aldaric acid upon oxidation is important for understanding structural similarities and differences among sugars.