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CHEMISTRY 29A
PRELAB WRITEUP AND EXPERIMENTAL REPORT SHEET
Octyl acetate
MW 172
BP 210ºC
O O
R C OH + R' OH R C O R' + H2O
1
RESULTS, DISCUSSION AND CONCLUSIONS*
This experiment demonstrated the Fischer esterification reaction of an acid with an alcohol to produce an ester. The ester chosen
for this was octyl acetate, which has the fragrance of orange. The reagents used for this esterification reaction were equal amounts
(0.01mol of each) acetic acid and 1-octanol. The actual weights of the reagents used were calculated from multiplying 0.01mol by
their respective molecular weights to obtain the weight that should be used. These amounts were added to the reaction mixture
along with 0.2g of Dowex, which acts as the acid catalyst in place of sulfuric acid. This makes it simpler to separate the final
aqueous product from the acid at the end of the reaction. The initial trial of the reaction was ruined because attempted rapid
heating of the mixture resulted in superheating that pushed a portion of the mixture out of the apparatus. Slower and steady
heating was used in the second trial to ensure stable movement of the vapor inside of the apparatus. While this vapor region
should have been kept in the middle of the top section of tubing in the apparatus, it mostly did not move any higher than the
sidearm section of the apparatus. This may have been due to the large size of the octyl acetate molecule, which hinders its
vaporization and movement up the apparatus. During the reaction, the hydroxyl group on acetic acid attacks a proton from the
acid catalyst, resulting in the removal of a molecule of water. The resulting positive 2º carbon is attacked by the hydroxyl group of
1-octanol, and the final octyl acetate results after a proton is pushed out of the hydroxyl group of 1-octanol. Since 0.01 moles of
each reagent were used, 0.01 moles of final product should be expected. The molecular weight of the product, octyl acetate, is
172, so the expected final weight should be about 1.72g. The experimental yield of this product however was only 0.9657g, which
was a 56% yield. This relatively low yield may be due to an incomplete reaction as much of the Dowex stuck to the roof of the
flask during reflux. It is not likely that product was lost to the sidearm because not organic layer was seen in the water removed,
and it was likely too heavy to move high up the apparatus. The experimental boiling point of the final product was 193ºC, which
was lower than the expected value of 210ºC for octyl acetate, which indicates the impurity of the product. The IR spectrum
supports this by showing the expected bonds of the product (C-H, C-O, and C=O), but shows other peaks as well, including a
large O-H stretch that may be from water or starting material (OH from acetic acid and 1-octanol).