1. Oxidation: Cyclohexanone from Cyclohexanol by Hypochlorite Oxidation
Chapter 22
Oxidation: Cyclohexanone from Cyclohexanol by Hypochlorite Oxidation

2. Purpose
In this experiment an alcohol is oxidized to a ketone with household bleach (sodium hypochlorite).
The product must be separated from the mixture by steam distillation and is extracted into the distillate with ether that is dried with Na2SO4. Removal of the ether leaves the product, cyclohexanone.

3. Reaction Mechanism
Intermediate alkyl hypochlorite ester is formed, which, by an E2 elimination, gives the ketone and chloride ion.

4. (Moles Product / Moles Starting Material) x 100 = % Yield
Comments
Follow Part 3, pp (microscale).
Follow the lab handout for all lab changes and experimental procedures.
Perform IR analysis of the product.
Calculate yield. Low yields are typical.
(Moles Product / Moles Starting Material) x 100 = % Yield

5. Safety
Flammable solvents are used in this experiment; keep away from open flame.
Glacial acetic acid is corrosive, handle with care.
Be firm but gentle when inserting the thermometer into the distillation apparatus. A broken thermometer is both a chemical (Hg) and physical (glass sharps) hazard.