Introduction:

Labs 2, 3, and 4 focused on extraction, recrystallization and thin layer chromatography and
melting point respectively. Lab 2 was conducted to utilize acid-base extraction for the isolation
of the three active components present in Goody powder. The purpose of Lab 3 was to purify
aspirin by recrystallizing it from Goody powder. Lab 4 was carried out to assess the efficiency of
the previous extraction in a qualitative manner and compare the melting point range of the
recrystallized aspirin with that of a standard aspirin sample.
Extraction is a technique used to remove water soluble impurities prior to distillation or
recrystallization. It involves the separation of a specific compound from a mixture based on
differences in physical or chemical properties such as solubility, boiling point, or polarity. Given
that extraction separates compounds based on intermolecular interactions, acids and bases can be
separated by changing the pH of the aqueous layer. Extraction is widely used in the production
of pharmaceuticals, agrochemicals, flavors, fragrances, and fine chemicals. In addition,
extraction is used to separate reaction products and by-products, and to remove impurities from
starting materials, intermediates, and final products.
Recrystallization is a common method for purifying solid compounds in organic chemistry. It
entails dissolving a crude solid in a suitable solvent at a high temperature to form a saturated
solution, then slowly cooling the solution to induce the formation of pure crystals. Impurities
either remain in solution or precipitate as a separate solid. The purity of the final product is
determined by the solvent's selectivity, the solvent used, and the cooling method.
Recrystallization is a highly effective method for purifying solid compounds and is used in the
synthesis of pharmaceuticals, agrochemicals, dyes, and fine chemicals. It is a crucial step in
analytical chemistry and in research and development, as pure compounds are essential for
studying the properties, structure, and behavior of molecules.
Thin layer chromatography (TLC) is a technique in organic synthesis used for compound
separation and identification. It involves using a mobile phase (usually a solvent) to separate a
mixture of compounds on a thin layer of adsorbent material, typically silica gel or alumina. As
the mobile phase moves up the TLC plate, the individual components of the mixture separate
based on their affinity for the stationary phase and the mobile phase. The plate is observed under
ultraviolet light and the stationary phase for each solvent is marked with pencil. The Rf is then
calculated, and the color change for each solvent is determined. This allows for the visualization
of individual compounds in the mixture, which can be identified by comparing their relative
positions on the plate to known standards or by the use of visualization reagents. Thin layer
chromatography is used in various stages of organic synthesis, including reaction monitoring,
compound purification, and product identification because it is a powerful and versatile tool for
organic chemists which facilitates the isolation and identification of individual compounds in
complex mixtures.
To accomplish the melting point experiment, a standard aspirin sample and recrystallized sample
are packed into separate capillary tubes and bounced off the bench surface a few times to
compress them into the closed end. Then the capillary tubes are placed in the melting point
apparatus, and the melting point ranges are recorded as the solids begin to transform into liquids.

Experimental:
Lab 2 started with wearing safety equipment such as gloves, goggles, and an apron. Then the
separatory funnel and ring stand apparatus were assembled as instructed. A goody powder packet
was collected and dissolved in 25mL of methylene chloride, then the mixture was filtered and
poured into the separatory funnel. 50mL of 1M NaOH was also added to the separatory funnel,
and the separatory funnel was vented during every inversion. Next the separatory funnel was
returned to the ring stand and allowed to form layers within the solution. One beaker was labeled
aqueous 1 and an Erlenmeyer flask was named organic 1 and each layer of solution was collected
into the appropriate beaker. Each layer was washed and inverted as needed according to the
flowchart and the layers were collected in appropriately labeled Erlenmeyer flask (organic) or
beaker (aqueous). Organic 4 was labeled with my initials, date, and lab section and placed in the
designated hood for the next experiment.
Lab 3 began with wearing safety equipment such as gloves, goggles, and an apron. Next a packet
of goody powder was added to a small Erlenmeyer flask and dissolved in 15mL of distilled water
after which a few boiling chips were also added to the flask. 5mL of water was added to a second
Erlenmeyer flask. Then a 125mL Erlenmeyer flask was attached to a clamp and ring stand to rest
on a hot plate as instructed and 3mL of water was added to the flask. A stemless funnel was
placed on top of the large Erlenmeyer flask and a fluted filter paper was rested in the funnel.
Then the first two Erlenmeyer flasks were placed on the hot plate next to the clamped assembly.
The hot plate was turned on and when the solution began boiling tongs were used to pour the
goody powder solution into the large Erlenmeyer flask through the filter paper. Once the filter
paper was empty, the original flak containing goody powder was rinsed with the extra hot water
and poured through the filter paper once more to solubilize any product that may have deposited
on the filter paper or funnel. After that, the hot plate was turned off and the large Erlenmeyer
flask was set down to cool. While cooling, the vacuum filtration apparatus was assembled as
instructed. Once the solution in the large Erlenmeyer flask was cooled, the flask was placed in an
ice bath until the product formed crystals. 5mL of water inside a small Erlenmeyer flask was also
placed in an ice bath. After 5 minutes with no crystal formed, the inside of the flask was
scratched with a glass rod to produce seeds. Once crystal formation was completed, the vacuum
was turned on and poured through the filter paper in the Buchner funnel. Any residual crystals
were washed from the flask using the cooled water and then poured into the Buchner funnel. The
crystals were allowed to dry for 15 minutes with the vacuum on. After filtration was done, the
crystals were collected into a small beaker and labeled with my initials, date, and lab section and
placed in the designated hood for the next experiment.
Lab 4 began with wearing safety equipment such as gloves, goggles, and an apron. Then the
mass of the recrystallized aspirin was measured using a balance and a weigh boat and recorded.
Next, two melting points capillaries were obtained from the common area. Both samples of
sample of recrystallized aspirin and standard aspiring were packed into different capillary tubes
and bounced off the bench surface, using the long glass tube, to compress them into the closed
end. The two samples were then placed into the holder of the melting point apparatus and the
switch was turned on while the rheostat knob was turned to 3.5. Then the samples were observed
as they were heated to determine the melting point range. The melting point ranges for each
sample was recorded and the melting point apparatus was turned off while the rheostat was
turned to zero. Also, the capillary tubes were disposed once they were cooled.
For the thin layer chromatography experiment, the standard samples of aspirin, acetaminophen
and caffeine were obtained from the common area. Recrystallized and extracted aspirin samples
with my initials were also obtained. Using a spatula tip, 2-4 mgs of each sample (which was
solid) was transferred to 4 different labeled test tubes and dissolved in 3mL of a 50:50
ethanol:dichloromethane mixture. The extracted aspirin was left as it was because it was in a
liquid state already. Then 20mL of 0.5% acetic acid/ethyl acetate was measured using a
graduated cylinder and poured into a 600mL beaker after which a watch glass was placed on top.
Next, a TLC plate was obtained from the common area and a pencil and ruler was used to draw a
line about 3mm from the edge. Small perpendicular marks were drawn to the line for the 5 lanes
in the experiment, then the lanes were labeled with unique identifiers as instructed. 5 capillary
tubes with both ends open were retrieved from the common area and each capillary tube was
rinsed by placing in 50:50 ethanol:dichloromethane and letting it bleed onto a paper towel. After
that each capillary tube was inserted into their respective solutions and placed on the
corresponding tick mark for that sample. Then the TLC plate was placed into the 600mL beaker
containing 20mL of 0.5% acetic acid/ethyl acetate using forceps. The plate was made to lean
against the side of the beaker with the silica side facing out and the watch glass was replaced on
top of the beaker. The solvent was allowed to run up the plate till it was about 5mm from the top
of the plate. After that, the TLC plate was removed using forceps and the solvent was marked
with a pencil. Once dried, the plate was placed under a UV lamp set to 254nm and the spots
visible under the UV light were circled. Then differences in color were recorded and each spot
was measured using a ruler to calculate the Rf.
 Results and Discussion:
Extraction Results

Aspirin, Acetaminophen, Caffeine

in Methylene chloride

Wash with 50mL of 1M NaOH

Acetaminophen and Aspirin (Aqueous Layer 1)

Caffeine (Organic Layer 1)

Acidify with 75mL of 1M HCl

Wash with 50ml of 1M HCL
Wash with 25mL of Methylene chloride

Acetaminophen Caffeine (Aqueous Layer 2)

(Organic Layer 2) NaCl (Aqueous Layer 4)

Aspirin (Organic Layer 4)

Basify with 75mL of 1M NaOH

Wash with 25mL of Methylene chloride

Caffeine (Organic Layer 3) NaCl (Aqueous Layer 3)

Aspirin is produced in Organic Layer 4. When 50mL of 1M NaOH was added to the mixture of
goody powder, aspirin was the most acidic of the three components, so it reacted with NaOH to
form a conjugate base. The conjugate base was further reacted with HCl which in turn produced
aspirin as an organic acid and the organic acid formed a layer below the aqueous solution of
NaCl.

Caffeine is produced in Organic Layer 3. When 50mL of 1M HCL was added to Organic Layer
1, Caffeine was the most basic, so it reacted with HCL to form a conjugate acid. The conjugate
acid was further reacted with NaOH which regenerated caffeine as an organic base and the
organic base formed a layer below the aqueous solution of NaCl.

Because acetaminophen has no basic or acidic properties, it remained in organic layers

throughout the extraction process.

Mass Balance and Precent Recovery

Mass of recrystallized aspirin: 0.143g = 143mg

Mass of aspirin in Goody powder packet: 520 mg

143
Percent recovery of aspirin: ×100 % = 27.5%
520

The percentage of recovery of aspirin is lower after recrystallization. This could be the result of
too much undissolved goody powder, improper fluting of the filter paper, and not rinsing the
container to solubilize product that may have been deposited, and not filtering with the Buchner
funnel correctly when carrying out the recrystallization experiment. Also, it could be the result of
inaccurate measurement of the mass of the recrystallized aspirin when weighing.

Melting Point

Melting point range of the aspirin from the recrystallization= 138°C - 140°C

Melting point range of the standard aspirin= 140°C - 141°C

The melting point range of recrystallized aspirin was similar to that of standard aspirin. This
implies that the aspirin obtained from recrystallization was pure and contained few to no
impurities.
TLC

Sample Migration (cm) Rf Value UV color

AS 6.0 0.895 Purple
AE 5.7 0.851 Purple
AR 5.8 0.866 Purple
CS 2.7 0.403 Purple
ACS 5.8 0.866 Purple

From the table above, caffeine is more polar than acetaminophen and aspirin because it has
traveled less distance and has a lower Rf value, whereas acetaminophen is less polar than
caffeine and more polar than aspirin. Aspirin is less polar than all other molecules because it has
traveled further and has a higher Rf value. Also, the extracted aspirin and recrystallized aspirin
samples moved equidistant to the standard aspirin sample, so this means that extracted and
recrystallized aspirin samples contain substantial amounts of pure aspirin.

Conclusion:

In conclusion, the objectives of performing Labs 2, 3 and 4 were achieved. Labs 2, 3, and 4
involved the extraction of aspirin, caffeine and acetaminophen, recrystallization of aspirin,
finding the melting point range of the aspirin obtained from extraction and recrystallization and
comparing the Rf value of the extracted and recrystallized sample. Aspirin, caffeine, and
acetaminophen were extracted from Goody powder; aspirin was recrystallized; melting point
ranges of the recrystallized aspirin sample and standard sample were determined; and Rf values
for each sample were calculated. The percent recovery of aspirin obtained from recrystallization
was 27.5%, which could have been caused by experimental errors and inaccurate weighing. The
melting point ranges of recrystallized aspirin and standard aspirin differed by 1°C - 2°C,
implying that the recrystallized aspirin was pure. These experiments could be useful to determine
the melting point ranges and Rf value of substances, extract compounds from a mixture, and
recrystallize substances in the future.