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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

Which of the following explains why chromic acid easily oxidizes 1° alcohols to carboxylic acids, but pyridinium chlorochromate (PCC) oxidizes 1° alcohols to aldehydes?

Chromic acid is an overall stronger oxidant, while PCC is an overall weaker oxidant.

The pyridinium of the PCC reagent is an antioxidant, reducing the carboxylic acid that is formed in the PCC oxidation, effectively cancelling out the extra oxidation.

Chromic acid has an aqueous solvent that can form a hydrate, which can be oxidized. PCC is not run in an aqueous solvent.

The key step in the chromic acid oxidation is favored by entropy, while the key step in the PCC oxidation is not.

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Verified step by step guidance

Understand the difference in oxidation products: Chromic acid oxidizes primary alcohols to carboxylic acids, while PCC oxidizes them to aldehydes.

Recognize the role of the solvent: Chromic acid is typically used in an aqueous environment, which allows the formation of a hydrate from the aldehyde intermediate.

Explain the formation of hydrates: In an aqueous solution, aldehydes can form hydrates (gem-diols), which are more easily oxidized to carboxylic acids.

Consider the solvent environment of PCC: PCC is used in non-aqueous conditions, preventing the formation of hydrates and thus stopping the oxidation at the aldehyde stage.

Conclude with the role of the solvent: The presence of water in chromic acid reactions facilitates further oxidation, while the absence of water in PCC reactions limits oxidation to aldehydes.