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Chapter 22 Oxidation: Cyclohexanone from Cyclohexanol by Hypochlorite Oxidation

Chapter 22 Oxidation: Cyclohexanone from Cyclohexanol by Hypochlorite Oxidation. Purpose. In this experiment an alcohol is oxidized to a ketone with household bleach (sodium hypochlorite).

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Chapter 22 Oxidation: Cyclohexanone from Cyclohexanol by Hypochlorite Oxidation

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  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.

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