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The Grignard Synthesis II Miniscale Synthesis of Triphenylmethanol from Ethyl Benzoate, Part 2. Organic Chemistry Lab II, Spring 2010 Dr. Milkevitch April 5 & 7, 2010. Today’s Experiment. Complete last week’s experiment Grignard synthesis React the Grignard with an ester Make an alcohol.

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the grignard synthesis ii miniscale synthesis of triphenylmethanol from ethyl benzoate part 2

The Grignard Synthesis IIMiniscale Synthesis of Triphenylmethanol from Ethyl Benzoate, Part 2

Organic Chemistry Lab II, Spring 2010

Dr. Milkevitch

April 5 & 7, 2010

today s experiment
Today’s Experiment
  • Complete last week’s experiment
    • Grignard synthesis
  • React the Grignard with an ester
    • Make an alcohol
last week
Last Week
  • Prepared the Grignard reagent
  • Reacted it with ethyl benzoate
    • In ether
  • Allowed it to sit until this week
  • This week:
    • Workup
      • Isolation & purification
      • Characterization
procedure part 2
Procedure: Part 2
  • Retrieve your RB flask from the hood
  • Take a look at it
    • Replace any lost volume with more ether
  • Remove the stir bar
  • Pure the reaction mixture into a 50 ml erlenmeyer flask that contains 8 g of ice
  • Rinse the reaction flask with ~2 ml of ether and add this rinse to the erlenmeyer with the ice
  • While stirring, carefully add 3M HCl dropwise to the solution
    • Use a glass stir rod to break up the solid
  • Continue to add acid until the lower layer is just acidic to litmus
    • Blue litmus turns red if the solution is acidic
  • Carefully pour the reaction mixture into your separatory funnel
    • Leave any unreacted magnesium in the flask
procedure con t
Procedure, con’t
  • Rinse the flask with 5 ml of diethyl ether
    • Add this to the separatory funnel
  • Reaction mixture should separate into 2 layers
  • Product is in the upper layer (ether layer)
  • Separate the layers
    • Into separate erlenmeyer flasks

1)One will have ether layer

2)One will have the water layer

    • Put the water layer back into the separatory funnel
  • Extract the water layer with 5 ml of diethyl ether
    • Allow layers to separate
    • Drain off the water layer into an erlenmeyer flask
  • Drain off the ether wash, add it to the original ether wash (#1 above)
  • Now, put all the ether layers into the separatory funnel
    • Extract it with 5 ml of DI H2O
procedure con t1
Procedure, con’t
  • Remove the water
    • Store in a beaker, set aside
  • Transfer the ether to a clean erlenmeyer flask
    • Dry over magnesium sulfate ~10 min
  • Decant or gravity filter the dried solution
    • Into a pre-weighed 50 ml erlenmeyer flask
  • Add a stir bar/boiling chip
  • Evaporate off ether using a hot plate
    • In the hood
  • Should get an off-white solid
    • Mixture of biphenyl and triphenylmethanol
  • Add 10 ml of petroleum ether
    • Stir thoroughly
    • Vacuum filter with a Buchner funnel
  • Weigh product
characterization
Characterization
  • Do a TLC
    • Plates are in the oven
    • Standards are in the hood
      • Standards: Triphenyl methanol, biphenyl
      • Spot these
      • Also spot your compound!
      • Develop your plate in methylene chloride
      • Visualize under UV light
  • Submit a sample for GC analysis
      • Dissolve a small amount of your compound in methylene chloride
      • Place in a small vial
        • Vials are in the hood
        • Label with your names
your report
Your Report
  • Formal lab report not required
  • Complete experiment worksheet