Chan Kyaw

Dr. Lawrence
Organic Chemistry Lab
9/15/14
Experiment 1 # Recrystallization of Organic Compounds
Introduction
In this experiment, the technique of purifying solids is explored. The solids ar
e first dissolved in an appropriate solvent and heated. Then the impurities are
filtered out by gravity filtration method and the solvent is left to cool down.
Once it s cooled, the solution crystallizes and the crystals are vacuum filtered
and dried. In this experiment, the phthalic acid is purified by the above method
. Next, the best crystallization solvent for benzoic acid is determined by mixin
g the acid with different solvents at room temperature, and at elevated temperat
ure to determine their solubility and the solution is left to cool down and form
crystals. In the final part of the experiment, an appropriate solvent for an un
known organic acid is determined and then purified using the methods from above.
Theory
Crystallization forms when the solution with the solute dissolved in sol
vent at high temperature is left to cool down. Since the solute is no longer sol
uble at low temperature, it comes together and crystallizes. Therefore, the solv
ent that has the property of dissolving the solute only at high temperature but
not at low temperature is chosen for crystallization.
The compounds used in the experiment are Phthalic acid, and Benzoic acid and unk
nown organic compound.
Phthalic Acid
Benzoic Acid
Molecular formula: C8H6O4.
Molecular formula: C7H6O2
Melting point: 210-211 degrees Celsius.
Melting Point: 125 degre
es Celsius
Density: 1.593 g/cm3
Density: 1.2659 g/cm3 at 15 degr
ess Celsius
Molar Mass: 166.14 g/mol
Molar Mass: 122.12 g/mol
Source: Advancing Science by Aldrick
Source: Sigma Aldrick Website
Experiment
Part A: Purification of Phthalic Acid (contaminated with charcoal)
About 1.0 g of impure mixture of Phthalic acid is placed in a 125 mL Erl
enmeyer flask and a boiling chip and tap water are added using a transfer pipett
e until all Phthalic acid is dissolved. The flask is then placed on a stirring h
ot plate. The hot water mixture is gravity filtered using a fluted filter paper
and stemless funnel into another flask. The flask is left to cool down to room t
emperature. Then the flask is placed in a ice-water bath and crystals start to f
orm. The crystals are filtered again using vacuum filteration method to remove a
ny water. For this method, the crystals are placed in a flask attached to vacuum
plug on the hood. The crystals are again let dry in air and the final product i
s weighed to determine the percent composition of the Phthalic acid in the origi
nal mixture. A Mel Temp apparatus is used to measure the melting point of the fi
nal product.
Part B: Determination of a crystallization solvent for Pure Benzoic Acid
The solubility of benzoic acid with seven different solvents are tested
in this part of experiment. The seven solvents are methanol, hexane, acetone, ac
etic acid, water, toluene and dichloromethane. About four or five crystals of be
nzoic acid are put inside each of seven test tubes. About 10 drops of each solve
nt is poured into the test tube and stirred to see if the solid dissolved at roo
m temperature. If the solid does not dissolve, it is heated by putting in inside
a water bath on a heater. If it dissolves, it is noted that the solid is solubl
e at elevated temperature for that solvent. If it is not dissolved, it is noted
accordingly. The dissolved solutions are left to cool down to room temperature a
nd placed in an ice bath to allow them to crystallize. For methanol and acetone,
some water is added to the solution from which some precipitates start to form.
The solutions with precipitates are placed in a water bath on a heater to deter
mine if they are soluble at elevated temperature.

Part C: Purification of an Unknown Organic Solid via Recrystallization

In the final part of the experiment, an appropriate solvent for an unkno
wn organic solid is determined using methods from Part B. A solvent that cannot
dissolve the solid at room temperature but can dissolve it at elevated temperatu
re is needed. The acetic acid is found to have this characteristic and is chosen
as the solvent. Using methods from Part A, the unknown organic acid is purified
and allowed to crystallized. Its melting point is also measured.
Part A:
Mass of impure phthalic acid measured:
1.0g
Mass of purified phthalic acid recovered:
0.10g
Percentage of recovered phthalic acid in the mixture:
10%
Measured melting point of purified phthalic acid:
208 C to 215 C
Part B
Solvent Ambient T
Elevated T
Acetic Acid
Insoluble
Soluble
Acetone Soluble Soluble
Hexanes Insoluble
Insoluble
Methanol
Soluble Soluble
Methanol + Water
Insoluble
Insoluble
Toluene Insoluble
Soluble
Water Insoluble
Insoluble
The optimal solvent for recrystallization of benzoic acid is toluene which is in
soluble at room temperature but soluble at high temperature.
Part C
Mass of impure unknown measured:
1.0g
Mass of purified unknown measured:
0.51g
Percent recovery of purified unknown:
51%
Measured melting point of purified unknown:
53 C to 59 C
Solvent used for recrystallization of unknown:
Acetic Acid
Results and Discussion
In this experiment, recrystallization is used as a method for purificati
on of a compound in an impure mixture as in phthalic acid from part A and unknow
n organic acid from part B. For this, the solubility of different solvents to di
ssolve the solids are tested and the one with the ability to dissolve the solid
only at high temperature but not at low temperature is chosen for crystallizatio
n to occur. The optimal solvent for phthalic acid is toluene but for unknown aci
d in Part C, it is acetic acid. It is found that the optimal solvent to dissolve
solids for crystallization is different depending on the solid. In Part A, only
10% of the pure phthalic acid is recovered from the impure mixture with charcoa
l. In Part C, for unknown acid which is almost entirely pure, only 51% percent i
s recovered. This can be because most of the mass is lost during the process of
transferring the solution from the flask to the filter paper and back.
Conclusion
In this experiment, the unknown organic compound is purified using the c
rystallization method learned from part A and part B. In part A, the phthalic ac
id mixed with charcoal is purified using water as a solvent. In part B, the appr
opriate solvent for recrystallization of benzoic acid is determined by testing i
ts solubility in seven different solvents. The solvent toluene with no solubilit
y at low temperature but full solubility at high temperature is chosen as the op
timal solvent for recrystallization. The skill from Part B is used to determine
the optimal solvent for unknown organic compound and the skill from part A is us
ed to purify the unknown compound using the optimal solvent. About 51 % unknown
organic compound is recovered. Most of the rest is lost during the process of tr
ansferring the solution from the flask to the filter paper and back. That can be
one of the sources of error. Careful transfer and retrieval of the solute can r
esult in higher percentage of recovery.
Post Laboratory Questions:
Part A:
Percent Recovery of dry product = 100%*( Mass of final product/ Mass of initial

mixture)
For phthalic acid,
Percent recovery = 100% * (0.1g / 1.0 g) = 10%
Carbon graphite does not have hydrogen bonds. It is a large sheet, and non-polar
molecule. Therefore, it is hard for any solvent to break the covalent bonds in
carbon to dissolve it.
Part C:
I think solubility is an important physical property that causes crystallization
. When the solid is soluble only at high temperature for a solvent, and the diss
olved solution is left to cool, the solubility disappears and the solute particl
es starts to come together to form crystals.
Gravity filtration and vacuum filtration will be used to isolate the unknown com
pound from methanol as in Part A. Melting point of the compound can be measured
to determine the identity the compound from two possible choices with different
melting points.