Lab 3_ Separations of Components of a Solid Misture (3)
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Experiment #3 – Separations – Report Form
Chem 2221L Fall 2021
The Separation of a Mixture and the Purification of its Components
The purpose of this experiment was to separate three solid mixtures into its specified
components (p-nitroaniline, benzoic acid, and benzil) and recover as much pure material of each
component as possible, while also obtaining melting points. This was a three week process, using
laboratory techniques such as: separation of the sample mixture using a separatory funnel, then
using a vacuum filtration for recrystallization of the three samples. The second week was
dedicated to purifying the sample by hot-filtration recrystallization and lastly during the third
week, using Thin-Layer Chromatography to analyze the polarity/separation difference of each
compound and comparing them to the pure mixture obtained during week 1.
The totality of this lab demonstrated the importance of separation and purification. Being
able to separate and isolate each component sanctions precise analysis and defining
characteristics of each sample. Organic chemists can then further their research, using required
pure samples, to study the properties, structures, and compositions of each component. During
the first part of the experiment, it emphasized the importance of acidity and basic components:
p-nitroaniline being the most basic (the first compound to be separated into the aqueous solution
while having the other two compounds still in the organic layer), followed by benzil, and then
benzoic acid being the most acidic solid. The third part of this experiment was focused on
obtaining melting points and predicting the purity of the separated solids to the data of the pure
solid melting points. Lastly, the significance of the fourth part of the experiment was centered on
understanding the difference in polarity among the three components, with p-nitroaniline being
the most polar and benzil being the most non-polar component. This is an important factor in
analyzing the results of the purity of each component.
Results:
Original Mixture Mass (g)
3.02
Mass of Percent
Recovery of
Each Compound
Compound
Mass of
Crude
Isolated Solid
(g)
Percent
Recovery
Mass of
Recrystallized
Compounds
(g)
Percent
Recover
y
Mass of
Purified
Compound
s (g)
Percent
Recovery
P-Nitroaniline
0.137
4.50%
-
-
-
-
Benzoic Acid
0.618
20.46%
0.133
21.52%
0.0038
2.86%
Benzil
1.713
56.72%
0.858
50.09%
-
-
Total
2.468
81.68%
0.991
71.61%
0.0038
2.86%
RF Values
P-nitroaniline: 0.6/5.3 = 0.113
Benzoic Acid: 3.1/5.3 = 0.585
Benzil: 3/5.3 = 0.566
Original Mixture: 0.6/5.3 = 0.113
Melting Points Obtained (Degrees Celsius)
P-nitroaniline: 137
Benzoic Acid: 119
Benzil: 96
Questions To answer.
1.
When is hot gravity filtration used and when is vacuum filtration used during
recrystallization (in this experiment)? What is the purpose of each type of filtration
(think about what you were collecting on the filter paper)?
a.
Hot gravity filtration is used when recrystallizing a compound that has recently
been dissolved at an increased temperature and while being cooled, goes through
the recrystallization process involuntarily. The purpose of hot gravity filtration is
to remove impurities/solid contaminants that are insoluble. Vacuum filtration is
mainly used to separate a solid (crystals or powdered compounds) from a liquid
solution. Using a vacuum and a filter-paper lined Buchner funnel, a “negative
pressure” is created, dividing the solvent (that passes through the filter paper) and
the solids (Benzoic Acid and Benzil) that are left on top of the filter paper. In this
experiment, the vacuum filtration was used for both benzoic acid and benzil
recrystallization while the hot gravity filtration was used for benzil
recrystallization before vacuum filtration.
2.
Why must the level of the solution in the developing chamber be below the spot on
your TLC plate?
a.
The level of the solution in the developing chamber must be below the spot on the
TLC plate to prevent the samples from dissolving in the solvent before the
capillary action in the developing jar is initiated.
3.
Why is anhydrous calcium chloride added to the “organic solution” from part 1?
a.
Anhydrous calcium chloride is added to the organic solution from part 1 because
it is a suitable drying agent that will remove the moisture and water from the
benzoic acid and benzil mixture after the p-nitroaniline is extracted.
4.
Discuss your percent recovery of the recrystallized benzil and benzoic acid.
a.
Recrystallization of both benzil and benzoic acid had a relatively high percent
recovery in contrast to the p-nitroaniline. According to research, the optimal
percent recovery is between 70-120%. Comparing my results to the optimal
percent recovery, deduces that the purification of each sample was less than
desirable. Also, when using the rotary evaporator in the earlier part of the
experiment, some of my solution was lost, due to a broken keck clamp, which
could potentially result in impurities in my sample of Benzoic Acid.
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5.
Comment on the success (or lack of success) of the separation and purification of the
three components. Use specific evidence obtained in the lab to support your
conclusions.
a.
The success of the separation and purification of the three components was a
difficult task. For example, when using the separation funnel, determining when
to stop the flow and distinguishing between the aqueous layer and the organic
layer was complicated. Also, when obtaining the melting point for each solution, I
noticed a slight decrease in temperature compared to the pure sample melting
points. This indicates that the separation of the mixtures was not as successful and
there were impurities left in the sample. Lastly, analyzing the thin layer
chromatography demonstrated a lack of success in separating and purifying the
three components. On my thin layer chromatography, there were Benzoic Acid
spots developed where the Benzil spots were. The thin layer chromatography
should have shown a clear distinguished spot between each component, but only
p-nitroaniline had a successful separation as its spot was clear and in the same
position as the pure mixture spot.
References:
https://dec.alaska.gov/spar/csp/faq/lab-data/#:~:text=If%20your%20report%20shows%20%E2%
80%9Cmatrix,done%20to%20overcome%20the%20interference.
https://chem.libretexts.org/Bookshelves/Introductory_Chemistry/Introductory_Chemistry_(CK-1
2)/02%3A_Matter_and_Change/2.10%3A_Separating_Mixtures
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5206469/
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