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

Monosaccharides - Strong Oxidation (Aldaric Acid)

Organic Chemistry

28. Carbohydrates

Monosaccharides - Strong Oxidation (Aldaric Acid)

5:43 minutes

Problem 20-14Bruice - 8th Edition

Textbook Question

a. Name an aldohexose other than d-glucose that is oxidized to d-glucaric acid by nitric acid.
b. What is another name for d-glucaric acid?

Verified step by step guidance

Identify the structure of D-glucose and understand its oxidation process to D-glucaric acid.

Recognize that D-glucose is an aldohexose, which means it is a six-carbon sugar with an aldehyde group.

Consider other aldohexoses that can undergo similar oxidation by nitric acid to form a dicarboxylic acid.

Recall that D-galactose is another aldohexose that can be oxidized by nitric acid to form D-galactaric acid, which is also known as D-glucaric acid.

Understand that D-glucaric acid is the common name for the dicarboxylic acid formed from the oxidation of D-glucose or D-galactose.

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Key Concepts

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

Aldohexoses

Aldohexoses are a class of carbohydrates that contain six carbon atoms and an aldehyde functional group. They are a subset of monosaccharides and include sugars like glucose, galactose, and mannose. Understanding their structure and reactivity is essential for identifying which aldohexose can be oxidized to d-glucaric acid.

Oxidation Reactions

Oxidation reactions involve the loss of electrons or an increase in oxidation state by a molecule. In organic chemistry, this often refers to the conversion of alcohols to carbonyls or carboxylic acids. In the context of aldohexoses, nitric acid acts as an oxidizing agent, converting specific sugars into their corresponding acids, such as d-glucaric acid.

D-Glucaric Acid

D-glucaric acid, also known as saccharic acid, is a dicarboxylic acid derived from the oxidation of aldohexoses. It is important in biochemistry and has applications in pharmaceuticals and detoxification processes. Recognizing its alternative name can aid in understanding its chemical properties and biological significance.