Experiment #2: Extraction

(Wednesday, May 25th)

PART A: Separation of Naphthalene and Benzoic Acid by One-Base Extraction
PART B: Design and Implementation of an Extraction Strategy
Part A is derived from Gilbert, J. C., Martin, S. F., Experimental Organic Chemistry, A Miniscale and Microscale Approach, 5th ed, p. 162.

Utilizing acid-base chemistry and a common purification method called extraction, mixtures of compounds will be
separated into the pure components. You will also learn how to dry and organic solution. In Part A of this experiment
you will separate and analyze a mixture of benzoic acid and naphthalene using the procedure provided in this handout. In
Part B of this experiment you will separate a mixture of compounds (assigned to you during the laboratory session) using
the knowledge and skills that you practice in Part A. Both parts will be completed during this laboratory session.
Textbook Reading:
G&M pg. 73-79, 155-163 (Extraction)
G&M pg. 85 (Drying organic solutions)
G&M pg. 64-67 (Gravity filtration, Fluted filter paper)
G&M pg. 67-69 (Vacuum filtration reassigned)
G&M pg. 36-39, 111-115 (Melting point reassigned)
(Note: from this point forward G&M will be used to
indicate the Gilbert & Martin Experimental Organic
Chemistry textbook)
Some Key Terms:
extraction, pH, pKa, aqueous solution, organic solution,
partition coefficient, solvent, solute, aspirator
Revisited terms: solubility, dissolution, filtrate, mother
liquor, percent recovery, melting point
Video Instruction:
You should view these videos as part of your prelaboratory preparations. Be aware that these videos will
show you a general technique but the compounds,
solvents, and quantities are not the same as those you
will use in the laboratory. Use these videos to become
familiar with the set-up and handling of glassware, but
think carefully about how your experiment may differ
from the video.
Extraction
https://www.youtube.com/watch?v=CyIA8NhMUl4&fe
ature=player_embedded#at=63
Extraction common problems
https://www.youtube.com/watch?v=_3G3MMcBYmY
&feature=player_embedded#at=65
Other Prelab Information:
Prepare your notebook according to the Notebook
Guidelines posted on NYU Classes under the
Resources tab, in the Course Documents folder.
Remember, you may NOT bring this handout (or
any piece of it) into the laboratory. Your only source
of information will be your prepared laboratory
notebook. Chemical Table is NOT necessary for this
experiment.
See the Material Safety Data Sheets (MSDS) posted
on NYU Classes under the Resources tab, in the
Experiment #2 subfolder.

a) Naphthalene
H
H
H
H
C
C
C
C
C
C
C
C
H
H
C
C
H
H
b) Benzoic Acid
H
H

C
C

H
C
C
H

C
C

O
C

O
O

Figure 1. (a) napthalene and (b) benzoic acid

represented using Lewis dot structure notation (left) and
line notation (right)

O
O

NaOH(aq)

insoluble in water
soluble in dichloromethane
NaOH(aq)

Na

H2O

soluble in water
insoluble in dichloromethane

No reaction

insoluble in water
soluble in dichloromethane

Figure 2. Reaction and solubility

PART A:
You will be provided with a mixture of naphthalene and
benzoic acid (Figure 1). You will not be told relative
amount of each compound in the mixture. Both of these
molecules are insoluble in water and soluble in
dichloromethane (Figure 2). Your task is to utilize acidbase chemistry and the extraction method to separate
the two compounds. Be sure that you understand the
purpose of each reagent and step as you will need this
understanding to be successful in planning your own
procedure in Part B of this experiment. Constructing a
flow diagram of each step is especially useful in
studying extraction.

Experimental Details: Remember, the procedure

supersedes procedures you may find in any other
resource.
Special CAUTIONS:
*The solutions of NaOH and HCl that you will use in
this experiment are corrosive and must be treated with
caution. If one of these solutions contacts your skin,
alert an instructor and run the area under cold water.
Dissolution. In an Erlenmeyer flask, dissolve 1 g of the
naphthalene and benzoic acid mixture in 15 mL of
dichloromethane (use more solvent if necessary to
dissolve all solid). Transfer the solution to the
separatory funnel.
Extraction. Add 10 mL of 2.5 M (10%) aqueous
sodium hydroxide (10% NaOH(aq)) to the separatory
funnel. Proper shaking and venting of the separatory
funnel is important so be sure to watch the videos and
read the text. Determine which layer is the aqueous
solution and which layer is the organic solution
(Described in the textbook. Also consider density). Use
tape to label one Erlenmeyer flask as Aqueous Layer
and another Erlenmeyer flask as Organic Layer
(remember to remove the at the end of the lab session).
Transfer the aqueous layer into the Erlenmeyer flask
labeled Aqueous Layer and the organic layer into the
Erlenmeyer flask labeled Organic Layer.
Recovery of Naphthalene. Dry the organic layer by
adding two micro-spatula scoops of anhydrous sodium
sulfate (Na2SO4) to the solution, followed by occasional
swirling for 10 minutes. If the solution remains cloudy,
add additional Na2SO4 as needed to complete the drying
process. Separate the solution from the Na2SO4 by
gravity filtration through a fluted filter paper or through
a cotton plug (your instructor will perform a
demonstration of these). Evaporate the dichloromethane
solvent by placing the flask in a hot water bath. When
the solution ceases to boil, remove the flask from the
hot water bath and allow it to cool to room temperature
to solidify the compound. Transfer the solid in the flask
to a pre-weighted and labeled small watchglass.
Recovery of Benzoic Acid.
Cool the aqueous layer in an ice-water bath before
slowly and carefully adding aqueous 3 M hydrochloric
acid (HCl(aq)). Precipitate should form upon sufficient
addition of 3 M HCl(aq) acid. Occasionally stir the
mixture with your glass rod to ensure distribution of the
acid. Based on the pKa of benzoic acid, what specific
pH must be reached in order for the majority of sodium
benzoate to be converted to benzoic acid, and thus
precipitate? Hint: The solution must be acidic (the
solution can be tested with the acid/base strips). Once
the precipitate ceases to increase upon slow acid
addition, the mixture should be cooled for an additional
10 minutes. Collect the solid by vacuum filtration using

a Bchner funnel, followed by rinsing the solid with a

small portion of cold water. Transfer the solid in the
flask to a pre-weighted and labeled plastic weigh boat
(not a watchglass).
Take your labeled (name and section #) samples on the
watch glass and weighboat to your section instructor.
They will submit the samples to be dried in the vacuum
oven.
Analysis. Determine the mass of the vacuum oven
dried naphthalene and benzoic acid. Also determine the
melting point of the crude and the purified material
using a Mel-Temp apparatus. You may want to begin
Part B if you are waiting for your sample to be dried or
to use a Mel-Temp apparatus.
Show your section instructor both of your recovered
materials, then dispose of the solids. Be sure to dispose
of the acidic and basic liquids in the appropriate waste
containers.
PART B:
During the laboratory session your instructor will
assign a different mixture to you. You will be told the
identity of the compounds in the mixture, relevant pKa
values, and the solubility of relevant compounds.
Using your skills and knowledge of why you performed
each step in Part A, you should be able to appropriately
modify the Part A procedure, if necessary, in order to
efficiently isolate one or more of the compounds in the
mixture (as instructed during the lab session). Note that
the assigned impure mixture, and thus the purification
strategies, will not be the same for all students. You are
expected to complete this entire task during the
laboratory session but, of course, you are welcome to
think about the possible scenarios you may encounter
and purification strategies prior to attending the
laboratory session. The textbook reading outlines the
key scenarios.
During the laboratory session, once you have written
the main steps of the procedure you plan to perform in
Part B, show it to your section instructor. If satisfactory,
your section instructor will sign your procedure
(approving safety, but not necessarily correcting the
procedure) and you will carry out the experiment that
you designed. Upon isolating the compound(s), weigh
the recovered material(s) and determine the melting
point of the crude and the purified material(s).
Postlab:
See NYU Classes Exp 2 folder.