Oxidation: Cyclohexanone from Cyclohexanol by Hypochlorite Oxidation

1
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
Comments

• Follow Part 3, pp 381-383 (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.