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Separating Acids and Neutral Compounds by  Solvent Extraction
Definition ,[object Object],[object Object],[object Object],[object Object],[object Object],Extraction Washing
[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],Chemistry of Extraction cyclohexane petroleum ether hexane toluene diethyl ether dichloromethane ethanol acetone methanol least   polar most polar Water Hydrocarbons/Ethers Chlorinated solvents Water
Acid-Base Extractions ,[object Object],[object Object],[object Object],Water Hydrocarbons/Ethers Chlorinated solvents Water p K a  =  4.2 p K a  =  16 p K a  =  4.2
The Extraction Setup
Make sure the  stopcock  of the separatory funnel is closed! ,[object Object],[object Object],[object Object],Experimental Procedure
4. Using your fingers to secure the cover, shake the mixture several times. 5. Vent the pressure by inverting and opening the stopcock.  (Vent often!) NOTE:   The cover is always secured   during the whole operation Experimental Procedure
6. Place the separatory funnel in the iron ring… 7. Remove the cover and allow the layers to separate. 8. Identify the layers (solvents).  (Don't throw anything away until sure.)   9. Remove bottom solvent by draining through the stopcock.  Pour the  upper solvent through the top of the funnel.  Experimental Procedure
  Use the  Microscale Flow Chart  on page 135 as a guide (see  the handout), but use the  Macroscale  procedure on page 134. Step 1.  The mixture of the three compounds is already prepared for  you.  (TA will give you the breakdown of the components!!) Step 2. Weak base  only deprotonates the  strong acid , which means  your compounds are in both phases. Step 3. Strong   base  deprotonates the  weak acid , which means  you will again have compounds in both phases. Step 4. Isolated  p -toluic acid  will need to dry in your drawer.  Don't  forget to pre-weigh your filter paper. Step 5. When heating, don't allow the temperature to exceed 60  degrees C.  Before adding HCl , cool the solution in an ice  bath.  Allow the isolated  p - tert -butylphenol  to dry in your  drawer.  (Pre-weigh paper!!)  ( Heating  is done in the hood.) Step 6. Pre-weigh a round bottomed flask (not a beaker).  Perform  distillation by  rotary evaporation  instead of the evaporation  procedure in the lab manual.  See 2 nd  handout for instructions.  Use the  house vacuum  to remove any residual solvent. Make Note of the Following:
Miscellaneous Notes ,[object Object],[object Object],[object Object]

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Extraction Fall 09

  • 1. Separating Acids and Neutral Compounds by Solvent Extraction
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  • 7. 4. Using your fingers to secure the cover, shake the mixture several times. 5. Vent the pressure by inverting and opening the stopcock. (Vent often!) NOTE: The cover is always secured during the whole operation Experimental Procedure
  • 8. 6. Place the separatory funnel in the iron ring… 7. Remove the cover and allow the layers to separate. 8. Identify the layers (solvents). (Don't throw anything away until sure.) 9. Remove bottom solvent by draining through the stopcock. Pour the upper solvent through the top of the funnel. Experimental Procedure
  • 9. Use the Microscale Flow Chart on page 135 as a guide (see the handout), but use the Macroscale procedure on page 134. Step 1. The mixture of the three compounds is already prepared for you. (TA will give you the breakdown of the components!!) Step 2. Weak base only deprotonates the strong acid , which means your compounds are in both phases. Step 3. Strong base deprotonates the weak acid , which means you will again have compounds in both phases. Step 4. Isolated p -toluic acid will need to dry in your drawer. Don't forget to pre-weigh your filter paper. Step 5. When heating, don't allow the temperature to exceed 60 degrees C. Before adding HCl , cool the solution in an ice bath. Allow the isolated p - tert -butylphenol to dry in your drawer. (Pre-weigh paper!!) ( Heating is done in the hood.) Step 6. Pre-weigh a round bottomed flask (not a beaker). Perform distillation by rotary evaporation instead of the evaporation procedure in the lab manual. See 2 nd handout for instructions. Use the house vacuum to remove any residual solvent. Make Note of the Following:
  • 10.