Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
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 Acids4h 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 - Weak Oxidation (Aldonic Acid)

Organic Chemistry

28. Carbohydrates

Monosaccharides - Weak Oxidation (Aldonic Acid)

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1:02 minutes

Problem 34c

Textbook Question

Predict the product of each of the following reactions.
(c)

Verified step by step guidance

Identify the functional groups present in the starting material. The molecule has an aldehyde group (CHO) and two alcohol groups (OH).

Recognize the reagent used in the reaction. Bromine in water (Br2, H2O) is typically used for the oxidation of aldehydes to carboxylic acids.

Understand the mechanism: Bromine water can oxidize the aldehyde group to a carboxylic acid. The reaction involves the formation of a bromohydrin intermediate, which is then hydrolyzed to form the carboxylic acid.

Predict the product: The aldehyde group (CHO) will be oxidized to a carboxylic acid group (COOH), while the alcohol groups remain unchanged.

Draw the structure of the product: The final product will have a carboxylic acid group in place of the aldehyde group, with the rest of the molecule remaining the same.

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Key Concepts

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

Weak Oxidation

Weak oxidation involves mild oxidizing agents like Br2 in water, which selectively oxidize aldehydes to carboxylic acids without affecting other functional groups. In the context of monosaccharides, this reaction targets the aldehyde group, converting it to a carboxylic acid, while leaving the rest of the molecule intact.

Aldehyde Functional Group

An aldehyde group is characterized by a carbon atom bonded to a hydrogen atom and double-bonded to an oxygen atom (CHO). In organic chemistry, aldehydes are reactive and can be oxidized to form carboxylic acids. Understanding the reactivity of aldehydes is crucial for predicting the outcome of oxidation reactions.

Monosaccharide Structure

Monosaccharides are the simplest form of carbohydrates, consisting of a single sugar unit with multiple hydroxyl groups and an aldehyde or ketone group. The structure of a monosaccharide determines its reactivity and the type of chemical reactions it can undergo, such as oxidation of the aldehyde group in the presence of Br2 and H2O.

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