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)

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7:32 minutes

Problem 20aBruice - 8th Edition

Textbook Question

How many aldaric acids are obtained from the 16 aldohexoses?

Verified step by step guidance

Identify that aldohexoses are six-carbon sugars with an aldehyde group at one end. There are 16 possible aldohexoses due to the variations in the stereochemistry at the four chiral centers.

Understand that aldaric acids are derived from aldohexoses by oxidizing both the aldehyde group and the primary alcohol group to carboxylic acids, resulting in a molecule with carboxylic acid groups at both ends.

Recognize that the oxidation of aldohexoses to aldaric acids results in a molecule that is symmetrical. This symmetry can potentially reduce the number of unique aldaric acids compared to the number of original aldohexoses.

Consider that each aldohexose can theoretically yield one corresponding aldaric acid. However, due to the symmetrical nature of aldaric acids, some of these acids will be identical to each other when derived from different aldohexoses.

Calculate the number of unique aldaric acids by considering the symmetry and possible identical structures resulting from different aldohexoses. This involves analyzing the stereochemical configurations that lead to distinct or identical aldaric acids.

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Key Concepts

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

Aldoses and Aldohexoses

Aldoses are a type of monosaccharide that contain an aldehyde group. Aldohexoses specifically refer to six-carbon aldoses, which include sugars like glucose and galactose. Understanding the structure and properties of these sugars is essential for determining the types of aldaric acids that can be derived from them.

Aldaric Acids

Aldaric acids are dicarboxylic acids formed by the oxidation of both the aldehyde and the primary alcohol groups in aldoses. For each aldohexose, the oxidation leads to a unique aldaric acid, which retains the carbon skeleton of the original sugar. This concept is crucial for calculating the number of distinct aldaric acids that can be produced from the aldohexoses.

Isomerism in Sugars

Isomerism refers to the existence of compounds with the same molecular formula but different structural arrangements. In the case of aldohexoses, there are multiple isomers due to variations in the arrangement of hydroxyl groups and the configuration around the chiral centers. Recognizing the different isomers is important for understanding how many unique aldaric acids can be formed from the 16 aldohexoses.