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)

Previous problemNext problem

3:06 minutes

Problem 23bWade - 9th Edition

Textbook Question

Draw and name the products of nitric acid oxidation of (a) D-mannose (b) D-galactose

Verified step by step guidance

Step 1: Understand the reaction. Nitric acid oxidation of a sugar typically results in the formation of a sugar acid. The primary alcohol group (-CH2OH) at the end of the sugar molecule is oxidized to a carboxylic acid group (-COOH).

Step 2: Draw the structure of D-mannose and D-galactose. Remember that D-mannose and D-galactose are both monosaccharides with the same molecular formula (C6H12O6), but they differ in the configuration of the hydroxyl group (-OH) at the C-2 position.

Step 3: Perform the oxidation reaction. Replace the primary alcohol group (-CH2OH) at the end of each sugar molecule with a carboxylic acid group (-COOH).

Step 4: Name the products. The product of nitric acid oxidation of D-mannose is D-mannonic acid, and the product of nitric acid oxidation of D-galactose is D-galactonic acid.

Step 5: Draw the structures of the products. Make sure to correctly represent the carboxylic acid group and the configuration of the hydroxyl groups in the product molecules.

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.

Oxidation Reactions

Oxidation reactions involve the loss of electrons or an increase in oxidation state by a molecule. In organic chemistry, this often pertains to the addition of oxygen or the removal of hydrogen. In the context of sugars like D-mannose and D-galactose, oxidation can lead to the formation of carboxylic acids or other functional groups, significantly altering the properties and reactivity of the original compounds.

Structure of Sugars

D-mannose and D-galactose are both monosaccharides, specifically aldoses, which means they contain an aldehyde group. Understanding their structural formulas, including the arrangement of hydroxyl (-OH) groups and the anomeric carbon, is crucial for predicting the products of their oxidation. The stereochemistry of these sugars influences how they react with oxidizing agents like nitric acid.

Nitric Acid as an Oxidizing Agent

Nitric acid (HNO3) is a strong oxidizing agent commonly used in organic chemistry to oxidize alcohols and aldehydes to carboxylic acids. When applied to sugars, it can oxidize the aldehyde group and potentially hydroxyl groups, leading to the formation of various oxidized products. The specific conditions of the reaction, such as concentration and temperature, can affect the extent and nature of the oxidation.