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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.
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.