Solubility and Extraction

Pre-Lab Assignment:
Complete the pre-lab cover page of the Lab-template Handout (available on the course website).
Draw a flow chart to represent which layer (organic or water) the benzoic acid goes into during
each phase of the procedure.
Learning goals:
Understand aqueous and organic solubility principles
Become acquainted with extraction techniques & use of separatory funnel
Understand how pH, pKa, and charge affect solubility.
Introduction:
This lab is designed to teach acid and base chemistry using liquid/liquid extraction. From
earlier chemistry classes you may have heard the saying like dissolves like, which refers to
polar compounds dissolving better in polar solvents and non-polar compounds dissolving better
in non-polar solvents. In this experiment you will dissolve benzoic acid in diethyl ether and
extract using water solutions of varying pH.

OH

OH

Ether

Dissolved
Benzoic acid

Solid
Benzoic acid

In ether, a relatively non-polar solvent, benzoic acid is soluble and therefore will be mostly
dissolved into solution.
O

OH

OH

H2O

Dissolved
Benzoic acid

Solid
Benzoic acid

In water, a polar solvent, benzoic acid is not soluble and therefore will remain mostly as a solid
in the solution.

Procedure:
You will be provided with a 250mL separatory funnel on your bench. Attach an iron ring to the
support bar on the hood and place the 250 mL separatory funnel in it (as shown in the picture
below).
Obtain the pre-weighed 250mg of benzoic acid from the hood.
Remove the cap from the separatory funnel and, making sure the
stopcock is closed (blue rod is perpendicular to the axis of the funnel),
combine the benzoic acid and 20 mL of diethyl ether in the separatory
funnel. Does the benzoic acid dissolve in this solvent? Why or why
not?

Place your fingers over the cap to secure it and invert the separatory
funnel. While holding the separatory funnel under the fume hood upside down, carefully open the drain valve to release pressure in the
funnel (see picture). Close the valve and gently shake the separatory
funnel for a few seconds. Using the same technique as before, release
the pressure on the separatory funnel. Repeat this process until the
benzoic acid has completely dissolved.
Warning: Liquid/liquid extraction using a separatory funnel produces
pressure when shaking. If you fail to vent the funnel during an
extraction, the pressure may build to a point that the cap is expelled
and the contents of the extraction lost.
Add 20 mL of 3M HCl to the separatory funnel and replace the cap.
Repeat the shaking/venting technique described above, five times.
Reminder: molar solutions are moles of solute in a liter of solvent.
For example, 3M HCl is 3 moles of HCl in 1 L of water.
After several shaking/venting cycles, replace the funnel in the iron
ring, remove the cap and allow the aqueous and organic (diethyl ether)
layers to separate. Why do these two layers separate from each other?
When the layers have separated you will be able to see a mirror-like
surface between the two layers. Label an Erlenmeyer flask acid
extract and drain the aqueous layer (caution: which layer is the
aqueous layer? Hint: water has a density of 1.00g/mL, and diethyl
ether has a density of 0.706g/mL. ) into it and set it aside.

Make sure you vent your

separation funnel away from you
and into the hood.

Add 20 ml of 3M NaOH to the remaining organic phase in the separatory funnel and repeat the
extraction procedure. Drain the aqueous layer into an Erlenmeyer flask labeled base extract
and set it aside. What does the NaOH do to the benzoic acid?
Carefully pour the diethyl ether into a beaker labeled neutral extract and place it in your hood.
Pour 10mL of ether from the beaker onto a watch glass and place in the back of the hood
Using a pipet and litmus paper, neutralize the acid extract by adding 6M NaOH dropwise
(caution: do not get this on your skin or clothes. If you get it on yourself, thoroughly wash it off
with water) until the solution is slightly basic. How is the NaOH neutralizing the solution?
Next, neutralize the base extract with 6M HCl until the solution is slightly acidic (see caution
above). One solution should have a relatively heavy white precipitate, while the other should
have no precipitate, why?
Observe your watch glass with the material from the flask labeled neutral extract. Most of the
ether should have evaporated. Is there any solid? Document which aqueous fraction has the
most precipitate.
Pour any residual ether into the waste bottle marked organic and your benzoic acid- water
mixtures into the bottle marked for benzoic acid disposal.

Post Lab:
Answer the following questions separate from your conclusion:
1. Which is the more polar solvent, water or diethyl ether?
2. When the pH of the solution is altered from neutral to basic, how is the solubility of
benzoic acid in the water layer affected? Why?
3. What is the function of a separatory funnel?
4. How many grams of sodium hydroxide are required to make 1 liter of a 3M solution
of NaOH? (show calculation)

Remember to include the required information that is described in the Lab Expectations
handout.
Conclusions/Discussion: The key to a good conclusion/discussion is answering why something
happened. Why did the reaction happen, why did you see a color change, and why was adding base
important etc.? Then answer how your reaction took place, including the chemistry, mechanisms, and
techniques involved.
Explanation of Data what does your data mean?
Chemistry, Mechanism, and Techniques explain the techniques used in lab. Examples: For extraction,
why were acids and bases used? For TLC, what is the importance of taking a TLC, how is solubility
involved? If your experiment did not work, you should explain how it should have worked!
Address Question asked in the Procedure Throughout the procedure questions regarding the
techniques are being asked. Make sure to address these questions completely and accurately to get full
points for your conclusion.