Extraction of a Three Component Mixture

Pre-Lab Assignment:
Complete the pre-lab cover page of the Lab-template Handout.
o Transcribe your own procedure using the procedure written below (Note:
You cannot have our copy of the procedure on your bench during lab; you
must create and work from your own written procedure. This is to ensure
youve read the lab and have a fair idea of what youre supposed to do!)
Create a detailed Flowchart mapping out the extractions separations.
Learning Goals:
Learn how acid/base chemistry is related to solubility
Learn liquid/liquid extraction techniques as a way of separating and purifying
organic compounds.
Learn how to construct a separations flowchart
Learn how to calculate percent recovery
Introduction:
Understanding how a molecule will react based on its properties is the core of organic
chemistry. One of the most easily understood structure-activity relations is acid/base
chemistry. In addition, the chemistry and thinking process in acid/base chemistry can be
extended to be the basis for many of the reactions that you will learn about in this class.
This lab will take advantage of acid/base properties in order to separate compounds using
liquid/liquid extraction techniques. The following compounds are present in the sample
that you will be given and need to be separated into their pure components.
O
O

OH

H2N

Benzoic Acid

Ethyl-4-aminobenzoate

9-Fluorenone

Note: Be kind to the environment and do not put organic waste down the sink.
Safety Issues:
1. Diethyl ether is flammable and intoxicating: do not use around an open flame and
do keep it inside your desk hood.
2. The aqueous sodium hydroxide solution is caustic (basic). If you get it on your
skin, it will dissolve the skin and/ or remove hair. If you or your clothes make
contact with either solution, immediately wash with tap water and advise your TA
that you got some on yourself.
3. The aqueous hydrochloric acid is acidic. If you get it on your skin it may cause
local irritation. If you or your clothes make contact with either solution,
immediately wash with tap water and advise your TA that you got some on
yourself.

Gen Chem Reminder: 3M HCl is not pure HCl. It is 3 moles of HCl(g) dissolved in 1 liter
of water. The water layers referenced throughout this lab are referring to these molar
solutions of acid or base.
Procedure:
In the main hood you will find a powdered mixture of containing 250mg of each of the
three compounds, Benzoic Acid, Ethyl-4-Amino Benzoate, and 9-Fluorenone. Add this
mixture to a clean separatory funnel (be sure the stopcock and closed before you add
anything to your funnel!) and then add ~20ml of diethyl ether (often called simply
ether.) Seal the funnel and shake briefly to fully dissolve the compound mixture.
Once dissolved, add ~20ml of 3M HCl (pH <0), seal the sep funnel, invert it (keeping
your fingers on the cap), briefly shake the mixture, and then open the stopcock to vent
pressure build up in the funnel. Note: Ether is extremely volatile and will easily build up
gaseous pressure from the heat of reaction. If you do not vent your stopcock every
few shakes, it may cause the lid to shoot off. Continue to shake vigorously and vent
periodically for ~30 seconds. After shaking, allow the two immiscible layers to fully
separate and then drain the bottom layer (water layer) into a 50ml Erlenmeyer flask and
label it acid extract. Note: If the lid is on your sep funnel when you try to drain it, it
may drain slowly or suck air bubbles up through the stopcock. With the top layer (ether
layer) still in the sep funnel, repeat the same process using 3M NaOH (pH >14), again
draining the bottom layer into a flask and label it base extract. Once both acid and base
extractions are finished, drain the remaining ether layer into a third flask (pre-weigh this
flask and write down the weight) labeled neutral extract.
Take your acid extract flask and slowly add to it
~8ml of 6M NaOH, then continue to add dropwise
additions of 6M NaOH until litmus paper shows a
shift from red to yellow/blue. Repeat the same with
your base extract using 6M HCl to neutralize it
until your litmus turns from blue to yellow/red.
Line a Hirsch funnel with a small filter paper (preweigh your filter paper!) that just covers the holes
on the bottom of the funnel. Dampen your filter
paper with a few drops of water and, hooked to a
vacuum as shown in the picture, slowly poor your
acid extract into the funnel and filter the precipitant
from your neutralized acid (what does your flow
chart say this precipitant should be?) Remove the
filter paper (precipitant and all) and set it aside.
Repeat the process for your base extract on a new
piece of pre-weighed filter paper.

Vacuum filtration setup using a 25mL Erlenmeyer Flask

and Hirsch Funnel. Remember to clamp your funnel.

Once you have isolated your two compounds, carefully transfer them (little filter paper
and all) to two larger pieces of pre-weighed filter paper and place them in your drawer to
dry. You can place your neutral extract with the ether in it directly in your drawer.
Note: Due to ethers volatility, no boiling is necessary and it will have evaporated
overnight. Do not put samples in a closed vial. They must be exposed to the air to

dry. You must allow at least 24 hours before weighing your compounds in order to let
them dry. If your compound appears wet, do not weigh it. Allow more drying time.
Once weighed, determine percent recovery. Put all solid wastes into the solids waste
container.
Post Lab:
Answer the following questions separate from your conclusions.
1. What is the pKa of each of the three compounds used in this experiment?
2. Given that aqueous conditions have a pH range of 0-14, why is a pKa of
30 not of interest in extractions using aqueous conditions? (remember that
pKa refers only to acidity of a molecule)
3. How did the pKa of each component play a role in this experiment?
4. How did changes in pH alter the polarity of ethyl-4-aminobenzoate?
5. Why is the pKa of fluorenone different than that of most ketone
compounds?
6. Give an example how the principles illustrated in this lab apply to
everyday life.
Include the appropriate material that was indicated in the Lab Report Expectations
handout available in the lab folder of the course webpage.