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The goal of this experiment was to synthesize the odor molecule, Berryflor, in a two step
synthesis process. The predicted percent yield is around 80% because minimal amounts of
reagents will be lost due to recondensing of vapors during the reflux.The first step of the
process included a reflux using an excess of ethanol to open the E-Caprolactone ring, while the
second step included a reflux that included acetic anhydride and the product of the previous
step, ethyl 6-hydroxyhexanoate. The synthesis resulted in a small percent yield of 10.18%. The
IR data also indicated that there was no remaining reactant because a peak around 3400 where
Introduction
Both steps of the Berryflor synthesis were carried out in a reflux apparatus under the fume
hood. In each step, the reactants were heated in the reflux chamber for around 50 minutes.
Refluxing involves heating the reactants to speed up the reaction, and allowing them to
continuously recondense and fall back down into the reflux flask. The first step of the reaction
involved opening a caprolactone ring using ethanol. Sulfuric acid was used to catalyze this
the carbonyl that was formed from the opening of the ring. The second step of the Berryflor
synthesis involved the acetylation of ethyl 6-hydroxyhexanoate, the product from the first step.
This process added an acetyl group to ethyl 6-hydroxyhexanoate using acetic anhydride and
sodium bicarbonate. TLC plates were also run at the end of each reflux to determine the
Materials
The chemicals used during both steps were: E-caprolactone, ethanol, sulfuric acid, diethyl ether,
6-acetoxyhexanoate, sodium sulfate, and sodium bicarbonate. The equipment used for this
experiment was: 100mL round bottom flask, 50mL round bottom flask, 50/100/200mL beakers,
reflux condenser, heating plate, magnetic stir bar, ring stands/clamps, tweezers, sand bath and
Procedure
A reflux condenser was attached to a 100mL round bottom flask on top of a bath and magnetic
stir plate to form a reflux apparatus. 0.5ml of E caprolactone, 50mL of ethanol, and .2mL of
sulfuring acid (dropwise) were added to the round bottom flask. The apparatus was then
attached to a variac and allowed to reflux for 50 minutes. A TLC column was then prepared
using a silica TLC plate with the product of the reflux and a 3% E-Caprolactone reference in
.5cm of 4:1 hexanol:acetone eluent. The plate was then stained with KMNO4 and heated until
pink. The contents of the reflux were then allowed to cool for 10 minutes before having .8g
sodium bicarbonate added until bubbling subsided. The contents of the flask were then
decanted into a 100mL flask. The flask was boiled on high heat until only ~1mL remained. The
contents of the flask were transferred to a separatory funnel, where 7mL of water and 7mL of
diethyl ether were added, then extracted. This process was repeated 3 more times each with
7mL of diethyl ether, and once with 7mL saturated NaCl. The organic layer was dried with
sodium sulfate and decanted into a 100mL beaker to sit for a week. The reflux process during
the first step was repeated using 2mL acetic anhydride, .5g sodium bicarbonate, and ethyl
6-hydroxyhexanoate from the previous week. The mixture was allowed to reflux for 50 minutes.
A TLC column was run using the same eluent as step one, with 1% 6-acetoxyhexanoate as a
reference. The round bottom flask was then allowed to cool to 70 C before 1mL of water was
added to remove excess acetic anhydride. The contents of the flask were then transferred to a
100 mL beaker where 10mL of DI water, 10 mL of Diethyl ether, and 2.4g sodium bicarbonate
were added and stirred. Once bubbling resolved. The mixture was transferred to a separatory
funnel and washed out twice with 10mL diethyl ether, and once with 10mL saturated NaCl in the
organic layer. The organic layer was then dried with sodium sulfate and decanted into a 50 mL
round bottom flask. Solvent in the organic layer was then removed in a rotary evaporator and
weighed. Both IR and NMR spectra were taken for the final product.
Results
The weight of ethyl 6-hydroxyhexanoate obtained was 0.01 grams. The weight of the final
Berryflor product obtained was 0.093g. The calculations were made based on e-caprolactone
and ethyl 6-hydroxyhexanoate because they were the limiting reagents of each step. As seen in
Equation 1, the percent yield obtained was 10.18%. IR data indicates a completed reaction with
only Berryflor product. The NMR data (used Simpson/Reimer’s Spectrum) shows 7 unique
IR Spectrum Data
0.5mL e−cap 1.03g e−cap 1mol e−cap 1mol E 6−H 1mol Berryf lor 202.25g Berryf lor
Equation 1. 1 1mL 114.1g e−cap 1mol e−cap 1mol E 6−H 1mol Berryf lor
=0.91 grams
Percent Yield=g obtained/g predictedx100= .0.093/0.91x100=10.18%
TLC Column Sketches
Reflux 1 Reflux 2
Discussion
The final yield of the Berryflor product was much lower than initially predicted. Only .093g were
obtained, meaning a percent yield of only 10.18%. The data of the IR spectra also supports this
yield. Despite all of the peaks for each functional group being present, the intensities of each
peak were relatively weak, indicating that only a small amount of berryflor was present. The TLC
column of the first reflux did not appear. The only spot that appeared was the caprolactone
reference. This means it is likely that the error resulting in the small yield was made during the
first reflux step. This may have been due to measurement errors, errors in lab technique, or the
wrong reactants used, resulting in only a small amount of ethyl 6-hydroxyhexanoate being
produced. The 2959.81 nm peak on the IR spectrum corresponds to C-H bonds found in
alkanes, the 1737.93 nm peak corresponds to the carbonyl groups, and the 1239.97 nm peak
corresponds with C-O esters. The lack of an OH peak at around 3400 nm means that there was
no remaining reactant. The HNMR spectrum has 7 unique peaks, corresponding to berryflor.
However, the carbon NMR showed 11 peaks, even though Berryflor only has 9 carbons. This
It was originally predicted that the synthesis would result in a high percent yield of around 80%.
However, the percent yield of the final product was actually only 10.18%. The weak peaks of the
IR along with the missing spot on the first TLC column indicates that an error was made during
the first step of the synthesis. Other than the small percent yield, all other data shows that the