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Solvent-free Oxidation of Secondary Alcohols to Ketones with Potassium Permanganate - Copper Sulfate

Page history last edited by jbfriesen 11 years, 6 months ago

“A Solvent-Free Oxidation of Alcohols in an Organic Laboratory” by John J. Esteb, Micheal W. Schelle, and Anne M. Wilson. Journal of Chemical Education, 80, p. 907 (2003)

Experiment Notes:

The procedure written for the oxidation of cyclohexanol to cyclohexanone can be easily adapted to methylcyclohexanol.

This is a smaller scale reaction than last week (0.00482 moles) so it may be advantageous to scale it up.

Work-up involves filtration and evaporation of the solvents – no distillation.

Positive

+ Alternative oxidation method that does not involve liquid-liquid separation

+ Solvent-free reactions generate good discussion of environmentally friendly reactions

Neutral

-/+ Why not grind alcohol into solid with the mortar and pestle?

-/+ An incomplete reaction was often had if students did not stir their reactant together sufficiently.

-/+ if there's no solvent why is reflux condensor necessary?

 

Negative

- Need quite a bit of solvent if you want to do a decent extraction of the product from the solid residue. This is rather inefficient and increases solvent consumption.

- Its hard to get the solid mass out of a round bottom.

- a mechanism is not given for the reaction.

 

Inquiry & Extension Ideas:

= A large variety of alcohols could be tried as substrates.

= A relatively simple experiment where modifications (amount of KMnO4-CuSO4-alcohol, reaction temperature, reaction time, etc...) could be made to study optimization strategies.

GC-FID chromatograms 2009

Photos 2009

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