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

OxidationOxidation

PurposePurpose

• In this experiment an alcohol is oxidized to a ketone In this experiment an alcohol is oxidized to a ketone with household bleach (sodium hypochlorite).with household bleach (sodium hypochlorite).

• The product must be separated from the mixture by The product must be separated from the mixture by steam distillation and is extracted into the distillate steam distillation and is extracted into the distillate with ether that is dried with Nawith ether that is dried with Na22SOSO44. Removal of the . Removal of the ether leaves the product, cyclohexanone.ether leaves the product, cyclohexanone.

Reaction MechanismReaction Mechanism

• Intermediate alkyl hypochlorite ester is formed, which, by Intermediate alkyl hypochlorite ester is formed, which, by an Ean E22 elimination, gives the ketone and chloride ion. elimination, gives the ketone and chloride ion.

CommentsComments• Follow Part 3, pp 381-383 (microscale).Follow Part 3, pp 381-383 (microscale).

• Follow the lab handout for all lab Follow the lab handout for all lab changes and experimental procedures.changes and experimental procedures.

• Perform IR analysis of the product.Perform IR analysis of the product.

• Calculate yield. Low yields are typical.Calculate yield. Low yields are typical.

(Moles Product / Moles Starting (Moles Product / Moles Starting Material) x 100 = % YieldMaterial) x 100 = % Yield

SafetySafety

• Flammable solvents are used in this Flammable solvents are used in this experiment; keep away from open flame.experiment; keep away from open flame.

• Glacial acetic acid is corrosive, handle with Glacial acetic acid is corrosive, handle with care.care.

• Be firm but gentle when inserting the Be firm but gentle when inserting the thermometer into the distillation apparatus. A thermometer into the distillation apparatus. A broken thermometer is both a chemical (Hg) broken thermometer is both a chemical (Hg) and physical (glass sharps) hazard.and physical (glass sharps) hazard.