Liquid-liquid extractions are essentially the only kind of extraction performed in the organic labs. The "liquid-liquid" phrase means that two liquids are mixed in the extraction procedure. The liquids must be immiscible: this means that they will form two layers when mixed together, like oil and vinegar do in dressing. Some compounds are more soluble in the organic layer and some compounds are more soluble in the aqueous layer. The ionic substance will be in the aqueous layer,usually lower layer, the nonionic ones in the organic layer, upper layer.
This is a pretty good intro. I'd be pleased to also see you discuss the acid/base chemistry of the process we are doing today, in addition to what you have here.


Williamson K.L., 2003. Macroscale and Microscale Organic Experiments 4th Edition. Boston (MA): Houghton Mifflin Company, p. . pages??
  • For this lab one would want to use the micro-scale glassware
  • Dissolve roughly 0.18 g of the mixture in 2 mL of MTBE in a reaction tube.
  • The add 1 mL of a saturated aqueous solution of sodium to the reaction tube.
  • Mix the contents of the tube thoroughly by pulling the two layers into a Pasteur pipette and expelling them forcefully into the reaction tube. Repeat process for roughly three minutes, then allow the layers to separate completely and then draw off the lower layer. (Usually the ionic substance will be in the aqueous layer)
  • Add another 15 mL of sodium bicarbonate solution to the tube, mix the contents as before, and add the lower layer to reaction tube two.
  • Add 2 mL of ether to tube 2, mix it thoroughly, remove the ether layer, and discard it. (Backwashing-removes any organic material the might contaminate the contents)
  • Add 1 mL of 3 M aqueous sodium hydroxide to tube 1, shake the mixture thoroughly, allow the layers to separate, draw off the lower layer using a clean Pasteur pipette, and place it in reaction tube 3.
  • Then to tube 1, add saturated sodium chloride solution, mic, remove the aqueous layer, and then add to the ether anhydrous calcium chloride pellets until the during agent no longer clumps together.
  • Wash it off with ether after the drying process is finished.
  • Then with hydrochloric acid, carry out neutralization, by adding drops of HCL and testing the solution with litmus paper.(Be extremely careful because much carbon dioxide is released in the neutralization)
  • Add a boiling stick to the tube and very cautiously heat the tube to bring most of the solid carboxylic acid into solution.
  • Allow the tube to cool slowly to room temperature and then cool it in ice.
  • Once crystallization occurred, use the Hirsch funnel to remove the crystals from the solution.
  • Collect the crystals on a tared piece of paper, allow them to dry thoroughly, and determine the percent recovery of the acid.

  • In the exactly same way, neutralize the contents of tube 3 with concentrated HCL (no carbon dioxide is released in this neutralization), heat the tube to bring most of the material into a solution, allow to cool slowly, then remove the solvent, and re crystallize the phenol from boiling water.

Weight of Unknown Mixture- 0.181 g

Contents of Tubes:

Tube 1, 1,4 dimethoxybenzene: 32.0°C-40.7°C These are your experimental values, right?
Tube 2, Benzoic Acid: 117.5°C-119.6°C
Tube 3, 4-tert-butyl-phenol 84.6°C-88.4°C

Table 1: Mass of Product Crystals
Object/Crystal Substance
Tube 1, dimethoxybenzene
Tube 2, benzoic acid
Tube 3, 4-tert-butylphenol
Filter Paper / Container
Filter Paper / Container + Product
Product Mass
The table above would be nice, but what's with all the zeros?
I would like to know what your product looks like.

Percent Recovery:
Tube 1, dimethoxybenzene:
0.019g / 0.181g * 100 = 10% Recovered

Tube 2,benzoic acid:
0.00g / 0.181g * 100 = 0% Recovered

Tube 3,4-tert-butyl-phenol
0.026g / 0.181g * 100 = 14% Recovered
calculations OK. sig figs OK.

I guess we've got an incomplete report here.
This report earns the following scores for: format (1/2) style (0.5/2) data (2/3) quality of result (1/1) quality of reported data (1/1) conclusion (0/2) error (0/1) post-lab Q (2 freebie points) for a total of 7.5/14. Note that some scores may vary from this score, based on participation levels.