Introduction

In this experiment we synthesized the ester, cholesterol nonanoate, and

determined its percent yield and produced a thermal liquid crystal display (LCD) to
determine the purity of the synthesized ester. The following reaction was in
coherence with the first part of the lab:
Nonanoyl Chloride + Cholesterol -----pyridine--- cholesteryl nonanoate +
pyridinuum hydrochloride
The first part of the lab was the actual synthesis of the ester which took place
in a fume hood. To do this cholesterol was measured into a test tube and dissolved
completely in pyridine. Adding pyridine helped because it acted as a solvent and
also reacted with the hydrochloric acid. Once reacted, the HCl is no longer able to
cleave the ester and hence there is an increase in the yield of cholesteryl
nonanoate. Nananoyl chloride was then pipetted into the test tube and then heated
for a number of minutes. The test tube was set to cool to room temperature and
then methanol was added. Cholesteryl nonanoate has low solubility in methanol,
and so it precipitates more easily in methanol. To help even more with the
precipitation, the test tube is then placed within an ice-bath. The newly formed
crystals were then separated from the supernatant by exposing them to a vacuum
and then left to air dry.
The second part of the lab was determining the melting point of pure 2acetonaphthone. The melting point of 2-acetonaphthone was determined by melting
it on a cylindrical steel block and measuring temperature with a digital
thermometer. The melting point was found more than once to ensure that the
results were precise and that any key qualitative signs could be observed. This
experimental value was then compared to the literature value to evaluate the ability
of this method in determining melting points of a substance. We then found the
melting point of the cholesteryl nonanoate crystals, and by comparing to the
literature value, the purity of the substance was determined.
The third part of the lab was making a LCD which was done by placing both
cholesteryl nonanoate and cholesteryl oleyl carbonate on a microscope slide. This
slide was then heated until the cholesteryl nonaoate began to melt. At this point the
two compounds were mixed thoroughly and then sandwiched by another
microscope slide. After cleaning and taping the sides, the newly formed LCD was
placed in ice. By observing color changes we determine if the ester was synthesized
because high molar mass compounds such as the ester display the unsusual optical
properties of liquid crystals.

Discussions:

Overall in this experiment there have been a few instances where

experimental values differed greatly from theoretical values. During the synthesis of
cholesteryl nonanoate, procedure step 4 states that ideally the solution should turn
yellow. This did not happen and neither did procedure step 5 where the solution
should turn cloudy. Though what these indicators represent is not stated in the lab
manual, it is evident as we progress through the lab, that an error was made at this
stage. This can be seen at 2 separate stages further into the experiment, the first
being the percent yield and the second being the melting point of cholesteryl
nonanoate. The percent yield in this experiment was a mere 13% which can be due
to a few reasons. Dealing with such a small mass, the smallest particles can make a
difference and so mass could have been lost during filtration or left a residue on
glass wear. Though we still had enough product to perform the next 2 parts of the
experiment, the amount synthesized was drastically lower than expected.
As for melting point, a possible source of error is the digital thermometer.
When measuring the melting point of 2-actonaphthone, there was a consistent level
of discrepancy between the literature value of 56 degrees celcius and the measured
value of 54.4 degrees celcius. It can be inferred that the thermometer provided
inaccurate results that were approximately 1.6 degrees celcius below the actual
value. Unfortunately the theoretical melting point of Cholesteryl Nonanoate is 74-77
degress celcius and we got almost double that value with 146 degress celcius and
so the thermometer inaccuracy cannot be a sufficient reason. This melting point
test informs us that with such a great difference it is likely that the ester was very
impure. The only reasonable explanation is that during the first few steps of the
procedure, some error was made, such than little or no ester was made. Rather the
solution must have stayed as one of the reactants such as cholesterol.
The LCD portion of the experiment was very unexpected in comparison to all
the results attained leading up to this part. Surprisingly the LCD screen produced,
clearly displayed color change which infers that the compound is of high molecular
mass. Yet why these observations were seen is unclear as it could be that there was
a little cholesteryl nonaoate produced and so it was this that caused the color
changes or maybe even the possibility that cholesterol can have properties of liquid
crystals.

Overall the errors made affected the melting point, and percent yield, but
didnt seem to have much of an effect on the LCDs.

Conclusion:
According to the results observed throughout this lab, in can be said that the
objective of synthesizing the ester cholesteryl nonanoate was accomplished but
very poorly. This is because if a somewhat pure ester had been created, it would
have been much closer towards the melting point of 74-77 degrees celcius. Yet a
small quantity must have been synthesized because the LCD did end up changing
color, which in the lab manual is said to test the overall success of the experiment.
To minimize error, in the future more time should be taken to ensure that the proper
compounds are being mixed, test tubes are clean and dry, and be more careful
when transferring and filtering a substance. In conclusion, all the requirements of
the lab were met but in the future, attempts can be made more accurate.