EXPERIMENT 4

THE SEPARATION AND PURIFICATION OF ORGANIC COMPOUNDS

Bea Bianca Dolores

BSMT - 1H

Recrystallization
a) 5 grams of impure acetanilide, 150mL of tap water and 2 drops of congo red were
placed together in a beaker. The contents were then heated and was constantly
stirred. As the acetanilide dissolved, 1 gram of animal charcoal was added as the
heating continued. The solution was then boiled and filtered through filter paper,
which resulted in a colorless filtrate. Equal amounts of filtrate were then collected
in two separate containers. One container was covered with a watch glass and
was set aside to be cooled slowly. The other container was placed in ice water
and was stirred while cooled.
Observation:
 Surface contamination (opened container) and occluded materials resulted to
small crystals while the covered container that had undergone slow-cooling
resulted in large crystals.
Explanation:
*container A = covered, slowly cooled
*container B = unconvered, cooled with ice water
 The impurities consisted of the sodium chloride and congo red.
 The animal charcoal added adsorped the congo red due to its porous property.
 The filtrate, called the “mother liquor”, consisted of both sodium chloride and
acetanilide.
 The difference of both container A and B was due to the surface contamination
and the process of cooling. Container A was slowly cooled and therefore resulted
to larger crystals as it gave more time for recrystallization of acetanilide and
therefore less occlusions (more time to reject the impurities, NaCl, during
recrystallization) compared to container B which had undergone a faster cooling
process, which had less time for recrystallization, and therefore resulted in
smaller crystals. Due to the covering of container A, there was less contamination
which resulted in lesser occlusions (lesser disturbance during recrystallization)
and therefore larger crystals in comparison with the smaller crystals in container
B which was uncovered.
b) Through gravity filtration, both crystals were filtered and were washed with tap
water. Both filter paper were then removed, with the crystals spread, and were
combined together and was allowed to dry overnight while covered with another
filter paper. The crystals were then weighed after it has dried and the percentage
yield was calculated.
Observation: (*solution)
Explanation:
 This indicates that only 33.33% of the theoretical yield was the obtained yield of
pure acetanilide from the experiment.

Extraction
a) 1g of benzoic acid contaminated with sodium chloride was placed in a beaker.
The mixture was then dissolved in 100mL tap water through heating. The
solution was cooled to room temperature and was then poured into a separatory
funnel. It was then followed by the addition of 5mL chloroform and was shaken
thoroughly. The two liquids were then allowed to separate into distinct layers.
After, the chloroform layer was withdrawn into an evaporating dish. The
extraction was repeated with 5mL of chloroform and both extracts were
combined. The upper layer was reserved for the testing of chlorides. The
chloroform extracts were then slowly evaporated on a water bath.
Observation:
 It was observed that the chloroform lied below the water layer (as it was more
dense compared to water) and was immiscible with it. The residue that resulted
from the evaporation of the chloroform was finer in size compared to the original
mixture.
Explanation:
 As the chloroform (nonpolar) was added to the solution, it dissolved the benzoic
acid (nonpolar), as the sodium chloride (polar) was dissolved in water (polar).
The separation into the distinct layers was due to the difference in polarity of both
solvents, therefore enabling the extraction of the chloroform along with the
benzoic acid. However, benzoic acid can be slightly soluble in water and thus
another 5mL of chloroform was added for further extraction. The extracted
solution were then evaporated which resulted to a residue of pure benzoic acid.

b) A drop of dilute nitric acid and a drop of silver nitrate was added to 10mL of the
upper layer.
Chemical Equation:
Observation:
 A white precipitate was observed to have formed from the reaction.
Explanation:
 The dilute nitric acid was used to produce an insoluble salt by neutralizing the
silver nitrate in it’s reaction with sodium chloride and thus forming the
precipitate.

Sublimation
a) 1g of benzoic acid contaminated with sodium chloride was placed in a clean and
dry 400mL beaker and was covered by the placement of an Erlenmeyer flask
half-filled with tap water. It was then heated very slowly. After the formation of
the sublimate over the base of the Erlenmeyer flask (and some at the sides of the
beaker), the flask was then removed. When the flask cooled, the crystals were
then scraped off with a clean sheet of paper and was collected on another sheet of
paper. The sublimate was then transferred in a clean and dry tests tube and was
reserved for the melting point determination.
Observation:
 Crystals of benzoic acid formed at the base of the flask (some formed at the sides
of the beaker), while the sodium chloride remained at the base of the beaker.
Explanation:
 The sublimation of benzoic acid was due to its high vapor pressure below its
melting point. Meanwhile, sodium chloride remained solid at the base of the
beaker because of its higher melting point