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

21. Aldehydes and Ketones: Nucleophilic Addition

Oxidation of Alcohols

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Oxidation of Alcohols

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Multiple Choice

Provide the major product for the following oxidation reaction.

Chemical structure of an aldehyde product from the oxidation of a diol.

Chemical structure of a diketone product from the oxidation of a diol.

Chemical structure of a ketone product from the oxidation of a diol.

Chemical structure of a secondary alcohol reacting to form a ketone.

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Verified step by step guidance

Identify the functional groups in the starting material. The compound is a cyclohexane ring with two vicinal (neighboring) hydroxyl groups, which is a 1,2-diol.

Recognize the reagent used in the reaction. Periodic acid (HIO4) is known for cleaving 1,2-diols into two carbonyl compounds.

Understand the mechanism: HIO4 oxidizes the 1,2-diol by breaking the C-C bond between the two hydroxyl-bearing carbons, forming two carbonyl groups (either aldehydes or ketones).

Determine the structure of the products: The cleavage of the C-C bond in the 1,2-diol results in the formation of two carbonyl compounds. In this case, since the diol is symmetrical, the products will be two identical aldehydes.

Draw the major product: The major product will be two molecules of the same aldehyde, each derived from one of the carbons that originally bore a hydroxyl group in the diol.