Jones oxidation

Jones Oxidation is an organic chemical reaction widely used for the oxidation of primary and secondary alcohols to carboxylic acids and ketones, respectively. Named after its discoverer, Sir Ewart Jones, this reaction employs a specific oxidizing agent known as the Jones reagent. The Jones reagent is a solution of chromium trioxide (CrO3) in diluted sulfuric acid (H2SO4), which can also be prepared using sodium dichromate in place of chromium trioxide. This mixture forms chromic acid in situ, which is the active species in the oxidation process[1][5].

The reaction mechanism involves the initial formation of chromic acid from the reaction of CrO3 with sulfuric acid. This chromic acid then oxidizes the alcohol, and in the process, gets reduced itself. For primary alcohols, the oxidation can proceed to form aldehydes and further to carboxylic acids, while secondary alcohols are oxidized to ketones[7]. The reaction is highly exothermic and typically yields high product yields. It is considered rapid and can be performed safely in acetone as a co-solvent to prevent over-oxidation of the alcohol[2][5].

Despite its effectiveness, the use of Jones oxidation has declined over time due to the development of milder and more selective oxidizing agents. Additionally, the environmental and health hazards associated with chromium(VI) compounds, which are carcinogenic, have led to a search for safer alternatives[5].

In summary, Jones Oxidation is a powerful method for oxidizing alcohols to ketones or carboxylic acids using chromic acid generated from chromium trioxide and sulfuric acid. However, due to safety concerns and the advent of gentler reagents, its use has become less common in modern organic synthesis.

Citations:

[1] https://www.organic-chemistry.org/namedreactions/jones-oxidation.shtm

[2] https://www.organic-chemistry.org/chemicals/oxidations/jones-reagent.shtm

[3] https://www.sciencedirect.com/topics/chemistry/jones-oxidation

[4] https://www.sigmaaldrich.com/US/en/product/aldrich/758035

[5] https://en.wikipedia.org/wiki/Jones_oxidation

[6] https://chem.libretexts.org/Courses/SUNY_Potsdam/Book:_Organic_Chemistry_II_(Walker)/19:_Oxidation_and_Reduction/19.06:_Oxidation_of_alcohols_and_aldehydes

[7] https://www.name-reaction.com/jones-oxidation

[8] https://www.organicchemistrytutor.com/topic/jones-oxidation/

[9] https://youtube.com/watch?v=Ii5qz0XD8aA

[10] http://www.adichemistry.com/organic/organicreagents/jones/jones-reagent-reaction-1.html