Jones Oxidation

Harsh Oxidation Method for Carboxylic Acids and Ketones

The Jones Oxidation is a harsh oxidation method used to oxidize primary alcohols and aldehydes to carboxylic acids. Additionally, this method can be used to oxidize secondary alcohols to ketones. ^{1 2 3 4 5}

Summary

The reaction entry summary. Find the general scheme and full summarized mechanisms here.

General Scheme

This section briefly summarizes what can and cannot undergo reactions.

• 1° Alcohols (Primary) get oxidized to Carboxylic Acids.
• 2° Alcohols (Secondary) get oxidized to Ketones.
• 3° Alcohols (Tertiary) do not get oxidized at all.
• Aldehydes are oxidized to Carboxylic Acids.

General Mechanism

This section briefly summarizes steps to find the product and perform the mechanisms.

Quick steps to finding the product for any alcohol

1. Identify the reagents.
2. Assign side chains (non alcohol part).
3. Selectively convert Alcohol to correct product based on alcohol type. Nothing else.
4. Keep the side chains (non alcohol part) the same and piece together the full molecule together again.

Full Secondary Alcohol to Ketone Mechanism

Full Aldehyde to Carboxylic Acid Mechanism

Full Primary Alcohol to Carboxylic Acid Mechanism

Always remember to repeatedly practice your mechanisms and getting your reagents correct. Take advantage of our materials and/or keep practicing on a whiteboard or paper until you get it right every single time.

References

1. Jones, E. R. H. The chemistry of the triterpenes. Part XIII. The further characterisation of polyporenic acid A. J. Chem. Soc. 1953, 457. DOI: 10.1039/jr9530000457

2. Jones, E. R. H. The chemistry of the triterpenes and related compounds. Part XVIII. Elucidation of the structure of polyporenic acid C. J. Chem. Soc. 1953, 2548. DOI: 10.1039/jr9530002548

3. Jones, E. R. H. The chemistry of the triterpenes and related compounds. Part XIX. Further evidence concerning the structure of polyporenic acid A. J. Chem. Soc. 1953, 3019. DOI: 10.1039/jr9530003019

4. Bowden, K.; Heilbron, I. M.; Jones, E. R. H. Researches on acetylenic compounds. Part I. The preparation of acetylenic ketones by oxidation of acetylenic carbinols and glycols. J. Chem. Soc. 1946, 39. DOI: 10.1039/jr9460000039

5. Heilbron, I. M.; Jones, E. R. H.; Sondheimer, F. Researches on acetylenic compounds. Part XV. The oxidation of primary acetylenic carbinols and glycols. J. Chem. Soc. 1949, 604. DOI: 10.1039/jr9490000604