Reese Kennedy, Sam Kwon, and Trey Davis The Packer Collegiate Institute, 170 Joralemon St,

Brooklyn, NY 11201, March 10, 2016.

Abstract: The experiment's goal was as follows: to use polarimetry to find the specific rotation of
six organic compounds and, by comparing this data, to identify one unknown compound. The
results of the experiment are extremely inaccurate because of a number of examined
procedural problems with the lab and the possibility of undetected human errors. However,
those facts aside the data did allow for a tentative prediction to be made regarding the identify of
the unknown substance. In reviewing the data and comparing the specific rotations for all six
organic compounds it can be postulated that the unknown substance is L- proline.

Introduction: Organic compounds - compounds containing carbon - are essential to understand

as they affect and make up almost all facets of life. These compounds determine almost all of
our bodily functions and are the components of almost all medicines on the market. As a result,
it is extremely important to understand how organic compounds function and react, depending
on their individual structures. The study of how molecular structure - or the arrangement of a
molecules atoms - affects the molecules function is called stereochemistry. One aspect of a
molecule that greatly affects its stereochemistry is whether or not the atom is chiral, or contains
a carbon atom bonded to four or more different groups. Chiral molecules have mirror images
that are not superimposable in three-dimensional space. Two non-superimposable molecules
are called enantiomers. Understanding enantiomers is vastly important, as one enantiomer of
the pair might react very differently than the other. This can be dangerous, especially when
concerning medical compounds, which are often chiral; one enantiomer might save a person's
life while the other could kill them. As a result, the ability to detect the concentration of a certain
isomer is important for the study of stereochemistry. In order to do so, scientists use a technique
called polarimetry, which capitalizes on the fact that enantiomers deflect light in opposite
directions, due to their differing structures. Polarimeters(see Figure 1) measure the

angles at which light is deflected off of molecules; this observed rotation can then be used to
solve for specific rotation values using Biots law( =[] l c). In Biot's law represents specific
rotation, [] represents observed rotation, l represents the length of the cell or sample
compartment(see figure 1) and c represents the concentration of the sample being tested. Using
these specific rotation values, the concentration of each enantiomer can be determined by
observing which enantiomers specific rotation is closer to the found value. Specific rotation can
also be used to identify chiral molecules. In the current experiment, specific rotation is used to
identify an unknown organic compound.

Figure 1.

Results and Discussion:

Recorded Observed Rotations of Six Organic Compounds

Tested Substance Observed

rotation(degrees)

Sucrose 115.5 degrees

D-(+)-fructose 98.002 degrees

L- arginine 167.89 degrees

L- proline 149.47 degrees

L- tartaric acid 231.6 degrees

 Unknown # 1 169.06 degrees

Figure 2.

Polarimetery Diagram. (n.d.). Retrieved March 10, 2017, from

1

http://www.tissuegroup.chem.vt.edu/chem-ed/spec/molec/graphics/polarim.gif

Comparison of Found and Accepted Specific Rotation Values for Six Organic
Compounds(includes corresponding percent error)
Tested Substance Found Specific Accepted Specific Percent Error(%)
Rotation(degrees) Rotation(degrees)

Sucrose 1.5 x 10^2 degrees 66 degrees 1.3 x 10^2%

D-(+)-fructose -64 degrees -92 degrees 30%
L- arginine 2.9 x 10^2 degrees 13 degrees 2.1 x 10^3 %

L- proline 1.3 x 10^2 degrees -86 degrees 2.5 x 10^2 %

L- tartaric acid 70 degrees 12 degrees 4.8 x 10^2%

Unknown # 1 2.0 x 10^2 degrees unknown unknown

Figure 3.

Our experimental results were extremely flawed. Our found specific rotations for each substance
differ immensely from the accepted values. This is made clear in Figure 3 which indicates
massive percent error for all of the tested substances. Figure 3 shows especially high error for
the L- tartaric acid(4.8 x 10^2%) and the L- arginine(2.1 x 10^3 %) samples, while Sucrose(1.3 x
10^2%) and D-(+)-fructose(30%) samples yielded slightly lower, yet still high, percent yield
values.The L- proline samples percent error was in the middle with a colossal 2.5 x 10^2 %
error. Given the drastically incorrect measured specific rotations values, fulfilling the labs goal to
identify the unknown compound was difficult. Figure 3 shows that the measured specific rotation
for the unknown substance(2.0 x 10^2) degrees was closest to the found specific rotations of L-
proline(1.3 x 10^2 degrees) and L- arginine(2.9 x 10^2 degrees). As a result, the unknown
substance is likely one of these two organic compounds and is most like L- proline as its specific
rotation value is the closest. Figure 2 also supports these predictions as the data shows that the
observed rotation of the unknown was again closest to L- proline and L- arginine. The
unknowns observed rotation was actually closer to that of L- arginine, but this data is deceptive
as L- arginine(.825 dm) was tested using a different cell
length than the unknown and L- proline(.905 dm). However, as I said before, these predictions
could be flawed as our data proved to differ significantly from the accepted specific rotation
values.

The aforementioned high percent error values can be accounted for by a number of different
errors in our experimental process. The first is the extremely long cell length used while testing
the observed rotations of the substances. The farther the light has to travel to reach the detector
the great chance for error. This is because there is a large chance that the light deflects off of
something other than the sample molecule when it has to travel such a long distance. However,
this potential source of error is not supported by the fact that the sample tested at the shortest
cell length(L- arginine) also had the high percent error. Another potential source of error is that
we only collected data for 15 seconds. This means that only a few points on the sine curve were
collected as opposed to the entire thing being filled out. As a result, the average angle
calculated by the polarimeter was likely flawed as the machine had little time to register the
angles. Yet another possible source of error is that the tests were not conducted at room
temperature. This is problematic as Biots law states testing must be done at room temperature.
Finally, there is a chance that our test solutions were simply prepared incorrectly; however, this
is doubtful as the other group produced equally inaccurate data. All of these possibilities
compiled it is not surprising that our percent error was so high. If the experiment was to be
re-done it would be paramount to take into account all four of the above errors. The most
obvious changes to experimental process would be the use of a shorter testing cell, a prolonged
data collection period, and temperature regulation.
Conclusion: The goal of this lab was to use polarimetry to calculate the specific rotation angles
of six organic substance and, through comparison, identify an unknown compound. However, as
a result of high error it is hard to regard the lab as a success. Since the recorded data was so
far from the accepted values and the unknowns specific rotation angle also being vastly different
than those of the other substance, it is nearly impossible to definitively identify the unknown
organic compound, as was the goal of this lab. That point aside, the data(see figure 1 and figure
2) supports the conjecture that the unknown is L- proline. With

necessary procedural changes this experiment could easily be conducted again with a higher
success rate. The simple changes mentioned above could easily lower the massive percentage
of error. These changes would hopefully, in turn, offer a more definitive answer to the identity of
the unknown substance.
Experimental Methods: Six solution were made: a 30% aqueous sucrose solution, a 30%
aqueous D-(+)-fructose solution, a 15% aqueous L- arginine, a 30% aqueous L-proline solution,
a 30% aqueous L- tartaric acid, and a 30% aqueous unknown solution. Next a blank cell, a test
tube only containing distilled water, was tested using polarimeter to establish the observed
angle of the blank cell. This angle would later be deducted from the found observed angles of
the solutions to find their true observed angles. The observed angles of the six solutions(before
the blanks angle was subtracted) were then found using the polarimeter. For the 15% aqueous
L- arginine solution a separate blank cells observation angle was record to account for the
different cell length. The true observed rotation angles were then found by subtracting the blank
cells observed angle from each of the six solutions recorded observed angles. These observed
angle measurements were then used to calculate each of the solutions specific rotation.

Bibliography

Lurain, A., Dr. (2017). Identification of Organic Compounds by Polarimetry. Packer Collegiate
Institute, 1-3. Retrieved March 10, 2017.

Polarimetry Diagram. (n.d.). Retrieved March 10, 2017, from

http://www.tissuegroup.chem.vt.edu/chem-ed/spec/molec/graphics/polarim.gif

Signature:

Date: March 10, 2017