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Addison Gasser Experiment 1 & 2

CHE 343-05

9/13/21

Identification of Two Unknown Solids (Recrystallization) and a Liquid (Siwoloboff’s Method)

For experiment 1 and 2, the objective is to determine the identities of two solids (macro and
microscale) and one liquid from a posted list of unknowns. For the solids this will be done through
recrystallization to purify the desired compounds in order to obtain an accurate melting point. For the
liquid, Siwoloboff’s method will be used to determine a boiling point. The boiling point and melting
points should match values on the posted list, which will then identify the compounds.
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Procedure (Siwoloboff’s Method - Liquid) Observations

Part 1: Setup Unknown liquid C.
Procedure (Microscale solid) Observations
An unknown liquid sample is obtained. Clear in appearance
Part 1: Set up Unknown Sample L
Small amount of liquid approximately 5 mL is put The setup was completed.
An unknown sample is obtained and Clear/White appearance and had a rigid/solid
into a small test tube. A small capillary is placed
approximately 100 mg is weighed out. structure for crystals.
closed-end down into the liquid. A thermometer
0.1120 g weighed out
is held against the tube with a rubber band,
A crude melting point is obtained for the sample, Crude melting point (degrees C): 81-89
flushed with the bottom of the tube.
and from this a solvent(s) is chosen from testing Possible solvents: Hot Ethanol/Warm Water
Part 2: Microscale Boiling Point determination As temperature rose and neared the boiling
what is suggested on the list of unknowns.
The setup is submerged in a water bath with an point, bubbling occurred.
Part 2: Purification
Procedure (Macroscale The Ethanol was heated to nearly boiling; the
octagonal stir bar. This watersolid)
bath is placed on a Observations
As the temperature continued to increase and
The solvent(s)
Part 1:hot
Setplate.is heated and used to completely
up The bath is heated until the boiling Unknown compound did
Samplenot Adissolve right away and it took
surpass the boiling point of the unknown liquid,
dissolve
An unknownthe unknown
sample issample,
obtained which
and iswill be some time inglittery
a hot water bath to dissolve.
point for the unknown sample surpassed. Pure White, appearance
the bubbling rapidly increased.
recrystallized,
approximately until
1.00 there
g is is hot
weighed saturated
out. Only
1.0025 a small
g amount
weighed out of solid impurities were left
The water bath setup is removed from the hot As the setup was allowed to cool the rapid
solution. undissolved.
A crudeplate and moved
melting point isto a cork ring.
obtained It issample,
for the allowed toCrude bubbling slowed
melting point until vapor
(degrees pressure dropped
C): 68-72
Any solid impurities undissolved are removed via The solution was hot gravity filtrated to remove
cool until it reached the boiling
and from this a solvent(s) is chosen from testing point of the below 1atm inside the
Possible solvents: Warm Methanol/Water capillary tube.
hot gravity filtration. And any discolored impurity impurities. No activated charcoal was used.
what isunknown
suggested again.
on theAt this point
list of vapor pressure
unknowns. At his exact instant a vacuum was created, and
is removed via activated charcoal, and the
Part 2:inside the capillary drops below 1atm, and a The methanol
Purification liquid of was
the unknown
heated tosample rose upthan
be hot rather the
charcoal removed again via hot gravity filtration.
vacuum is created.
The solvent(s) heated and Partused
2 is to
repeated
completelyas many warm,capillary. This was
this dissolved the repeated
compound twice.
quickly.
This leaves a homogeneous solution of the
times
dissolve the as neededsample,
unknown to determine
whichthewillboiling
be point. Both trials in
Small impurities had thequantity
large vacuum were
in theleft
capillary occur
unknown sample and the solvent(s).
recrystallized, until there is hot saturated at approximately 81, 83
behind, based on appearance likely sand. and 84 degrees Celsius.
The solution is cooled until sufficient Allowed to cool to room temperature, crystals
Part 3: Characterization
solution. The boiling point was found to be approximately
recrystallization has occurred. This began to form slowly over time, in clusters.
Theimpurities
Any solid boiling point is determined
undissolved after a couple
are removed 82.67 C, which
via The impurities was very using
were removed near the literature
a hot gravity value
recrystallized/purified product is removed from Adding a small amount of cool water, around 10-
runs of Siwoloboff’s method. This experimental
hot gravity filtration. And any discolored impurity filtration. of 82 C.
solution through vacuum distillation. The crystals 15 mL, more crystals were pulled out of solution.
boilingviapoint
is removed is matched
activated withand
charcoal, a literature
the valueThere
to The was unknown sample Csowas
no discoloration, found to was
no charcoal be
are rinsed with cold solvent(s) to further pull off The solution was cooled further in an ice bath for
determine the Unknown.
charcoal removed again via hot gravity filtration. used. Acetonitrile.
any remaining impurities. The filtrate is analyzed approximately 10 minutes. The resulting crystals
This leaves a homogeneous solution of the
for product and any remaining is recrystallized were removed using vacuum filtration. These
unknown sample and the solvent(s).
and collected through the same process. final purified crystals were quite different than
The solution is cooled until sufficient Allowed to cool to room temperature, crystals
the impure compound.
recrystallization has occurred. This began to form on their own in sheet-like
The purified crystals were more powdery and
recrystallized/purified product is removed from formations.
lacking structure. Pure white in appearance.
solution through vacuum distillation. The crystals Adding a small amount of cool water, around 10-
Part 3: Characterization Final weight recorded: 0.1035 g
are rinsed with cold solvent(s) to further pull off 15 mL, more crystals were pulled out of solution.
The final product is allowed to dry, then a melting %recovery = (0.1035/0.1120)*100% = 92.41%
any remaining impurities. The filtrate is analyzed The solution was cooled further in an ice bath for
point and mass is obtained. From this mass and The melting point for the purified compound was
for product and any remaining is recrystallized approximately 10 minutes. The resulting sheet-
crude mass, the percent recovery is calculated. found to be 87.5-90.
and collected through the same process. like crystals were removed using vacuum
The Unknown sample L was determined to be 1,4
filtration. These final purified crystals were much
- dibromobenzene, as the melting point matched
whiter and more gleaming in appearance than
its literature value.
the impure compound that preceded
recrystallization.
Part 3: Characterization Final weight recorded: 0.540 g
The final product is allowed to dry, then a melting %recovery = (0.540/1.0025)*100% = 53.87%
point and mass is obtained. From this mass and The melting point for the purified compound was
crude mass, the percent recovery is calculated. found to be 69-72.
The Unknown sample A was determined to be
Biphenyl, as the melting point matched its
literature value.
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Data/Results

The following equation was used to calculate percent recovery for both macro- and microscale.
% recovery = (mass of pure crystals/mass of crude solid) x 100 %

Unknown Solid Initial Final % Crude Melting Observed

Sample Weight Weight Recovery Point Melting Point
A (Macro) 1.0025 0.540 53.87 68-72 69-72
L (Micro) 0.1120 0.1035 92.41 81-89 87.5-90

Unknown Liquid Sample Trial 1 b.p. (Celsius) Trial 2 b.p. Trial 3 b.p.

C 83 84 81

Recrystallization is one way to

remove impurities from an
unknown compound. Once a
compound has been purified, its
physical properties can be
further assessed. By comparing
the
melting point of a known solid
to the melting point of an
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unknown solid, the unknown

may be
able to be identified. Identifying
a liquid can be determined by
comparing boiling points of
known and unknown liquids.
Siwoloboff’s method was used
to determine the boiling point of
the
unknown liquid.
Discussion

The techniques performed in these experiments are useful ways of determining an unknown in
the solid and liquid state. Through recrystallization a compound can be purified, and the compound of
interest can be isolated. Overall, the experiments were a success as there was purification,
recrystallization, and identification of both solid unknowns. And an accurate measure of boiling point for
the unknown liquid sample was determined using a successfully accurate Siwoloboff’s method.

This experiment demonstrates a

principle most are
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already familiar with and that is

that solids are more likely to
dissolve in a warm liquid than a
cold one. An impurity will not
dissolve when heat is applied,
and they can be removed from
the
hot solution through filtration.
Once impurities have been
removed the purified compound
can
begin to cool and reform the
bonds that it typically exhibits.
This experiment demonstrates the trend of solids being more soluble in heated conditions and
insoluble at room temperature or cooler. And that an impurity will not dissolve as heat is applied, and
they must be removed from the solution through hot gravity filtration, or for discoloration activated
charcoal. Once impurities have been removed the purified compound can begin to cool and reform the
bonds that it typically exhibits between the desired pure compound. This pure compound can then be
tested for a melting point which in turn is used to identify a specific compound based on literature
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values. It should be an easy process if the correct solvent was used, impurities removed, and vacuum
filtration done cautiously.

The Siwoloboff’s method is used to determine a microscale boiling point. The idea is to heat the
unknown liquid evenly in a water bath to the unknown liquids boiling point. A capillary tube is inverted
face down into the test tube filled with unknown to provide an indication of when that liquid is boiling.
There is vapor pressure in the air space of the capillary tube that builds as the liquid is heated. The vapor
pressure in the capillary tube increases with heat because the evaporation rate of the liquid increases.
With no way for the evaporating molecules to escape from the capillary tube they eventually force their
way out of the tube. The vapor pressure has exceeded the atmospheric pressure which causes bubbles
to rapidly come out of the capillary tube. It is safe to assume that the boiling point has been surpassed
and the heat can be removed. The bubbling slowly subsides as the vapor pressure decreases. Boiling
point is defined as when vapor pressure equals atmospheric pressure. As soon as the bubbling stops a
small amount is sucked back into the capillary tube and at that instant the temperature is recorded.
Essentially the vapor pressure is dropping right below atmospheric pressure creating suction in the
capillary tube. It is a quick occurrence and with multiple trials can be very accurate if done well. With
unknown liquid C (Acetonitrile), it was easy to pinpoint an approximate boiling point of 82 C.

POST-LAB QUESTIONS

A. Haylee’s first mistake was that she was in a rush. Being in a rush in a chemistry lab is dangerous
to yourself and everyone else around you. Haylee should have taken her time and allowed the
Digi melt to increase heat at a slower rate. If she would have used 2 C as her ramp rate it would
have given her time to record both temperatures and a more accurate range.
B. Matt should have allowed the solvent to cool before attempting to add the stir stick or he should
have simply started over with fresh room temperature solvent and added the boiling stone
then.
C. PJ should dissolve her compound in the hot ethanol and then perform a hot gravity filtration to
remove impurities. A second filtration may be needed if she used activated charcoal to remove
colored impurities. Once her crystals have cooled, she should perform a vacuum filtration and
wash her crystals with cold water. PJ will be using a mixed solvent system.
D. She used a long-stemmed funnel, and the reforming crystals clogged the stem not allowing good
product to filter through and pushing impurities on the walls of the funnel. It appeared shiny
because her crystals were beginning to form on the sides of the funnel.
E. Taylor should have used the same mixture of methanol and water, waited for the crystals to
reform after placing it in an ice bath and then poured the crystals in the Buchner funnel.
F. Water boils at 100 C, which is higher than all but one of the possible liquid unknowns. Once the
water reached its boiling point the temperature begins to remain constant. Sam is safe to
assume that his liquid is Toluene since it hasn’t started boiling and the water isn’t going to get
any hotter.
G. There is vapor pressure in the air space of the capillary tube that builds as the liquid is heated.
The vapor pressure in the capillary tube increases with heat because the evaporation rate of the
liquid increases. With no way for the evaporating molecules to escape from the capillary tube
they eventually force their way out of the tube. The vapor pressure has exceeded the
atmospheric pressure which causes bubbles to rapidly come out of the capillary tube. It is safe
to assume that the boiling point has been surpassed and the heat can be removed. The bubbling
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slowly subsides as the vapor pressure decreases. Boiling point is defined as when vapor pressure
equals atmospheric pressure. As soon as the bubbling stops a small amount is sucked back into
the capillary tube and at that instant the temperature is recorded. Essentially the vapor pressure
is dropping right below atmospheric pressure creating suction in the capillary tube.