tags
mentholalcoholdichronatebisulfitesodaCyclohexanolisopropanoldichromatecyclothexanonechromic

video tutorial Cyclohexanone via Jones reagent oxidation

  • Objective: oxidize cyclohexanol to cyclohexanone using Jones reagent (potassium dichromate in sulfuric acid).
  • Jones reagent preparation: dissolve 55 g potassium dichromate in 200 mL water, add 80 mL concentrated sulfuric acid, heat to dissolve to chromic acid; after acid addition the mixture reaches about 90°C.
  • Reaction setup: use a large flask with stirring and a thermometer; add 50 g cyclohexanol (3 equivalents per dichromate); form a milky emulsion; add chromic acid solution slowly, monitor temperature; keep the reaction around 50–65°C, and allow several hours for completion; cooling can speed things up but avoid exceeding 65°C.
  • Workup: neutralize excess dichromate with about 10 g oxalic acid (or isopropanol as an alternative); set up for distillation in the same flask; steam distill the product (the product is described as an acetate in this setup); collect distillate as an azeotrope with water; accumulate until about 150 mL, then continue; stop when no more top layer distills; combine distillates.
  • Extraction and drying: saturate the aqueous layer with salt to extract product; separate layers; extract the top organic layer, dry with MgSO4, decant after drying; yield 42 g of cyclohexanone as a colorless liquid (86% yield, without organic extractions).
  • Product verification: test with saturated sodium bisulfite; formation of a crystalline bisulfite adduct confirms a ketone; for other secondary alcohols, check boiling point, water solubility, and azeotrope behavior to adjust workup accordingly.
  • Outlook: mentions future ideas for cyclohexanone applications.

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