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Introduction:
Esters are formed by the reaction of an organic acid with an alcohol. Whenever an
ester is made, the possible contents in the reaction vessel are the starting materials, the
organic acid and alcohol, and the products, the ester and water. In this experiment, an
ester will be produced, the contents of the reaction vessel analyzed by GC, the peaks
identified by comparison with standards, and the percent of ester determined. The percent
yield of the reaction will then be calculated.
Purpose:
The purpose of this laboratory activity is to determine the percent yield of an
esterification reaction.
Equipment/ Materials:
GC and associated supplies
Beral pipets
scissors
beaker
hot plate
cork to fit beral pipet
1 mL automatic pipet
ethanol
acetic acid
ethyl acetate
ion exchange resin
styrofoam cup
analytical balance
Safety:
22-B-1
Procedure:
1.
Prepare a hot water bath by placing about 100 mL of water in a beaker and heating
it to 80 C on the hot plate.
2.
3.
Add a small amount of ion exchange resin to test tube 1. Insert a cork gently into
the test tube.
4.
5.
Remove the cork and add 2.000 mL of ethanol. Replace the cork and record the
mass of test tube 1, cork, and contents.
6.
Remove the cork and add 1.000 mL of acetic acid. Replace the cork and record
the mass of test tube 1, cork, and contents.
7.
8.
Inject a 5 microliter sample of the reactant mixture in test tube 1 into a GC.
Record GC and chart recorder settings.
9.
10.
Pour the hot water into a styrofoam cup to serve as a constant temperature hot
water bath.
11.
Place the test tubes into the hot water bath at 70-80 C for 15-20 minutes. While
heating, continue with steps 10-12.
12.
Inject 5 microliter samples of ethanol, acetic acid, ethyl acetate, and water into the
GC. Record GC and chart recorder settings.
13.
22-B-2
14.
Carefully cut out the ethyl acetate peaks for the 1-5 microliter samples and record
the mass of each peak.
15.
After the 15-20 minute reaction time is concluded, remove the test tubes from the
hot water bath, and dry the outside of the tubes.
16.
Record the mass of each test tube, cork, and product mixture.
17.
Inject a 5 microliter sample of the product mixture from test tube 1 into the GC.
Identify each peak.
18.
Carefully cut out the ethyl acetate peak and record the mass of the peak.
19.
20.
Prepare a graph by plotting the mass of ethyl acetate peak (y) vs. volume of ethyl
acetate used (x).
21.
22-B-3
Name ______________________________
Period ______________________________
Date _______________________________
Test tube 2
Test tube 3
mass of peak
5
4
3
2
1
22-B-4
Table 4
Trial 1
Mass of ethanol used
Mass of acetic acid used
Mass of reactant mixture
Mass of product mixture
Mass of H2O peak in 5 L react mix
Volume of H2O in 5 L reactant mix
% of H2O in reactant mixture
Mass of H2O in reactant mixture
Theoretical mass of H2O produced
Theoretical mass of ethyl acetate produced
Mass of H2O peak in 5 L product mixture
Volume of H2O in 5 L product mix
% H2O in product mixture
Mass of H2O in product mixture
Mass of H2O produced
% yield H2O
Mass of ethyl acetate produced
% yield of ethyl acetate
Average % yield water ______________________
Average % yield of ethyl acetate _______________
GC Conditions:
injection port temp:__________
column temp:_________
outlet temp:_________
bridge current:__________
detector temp:_________
attenuation:__________
chart speed:__________
22-B-5
Trial 2
Trial 3
Questions:
1.
2.
3..
If 1.3 g of 95 % ethanol and 1.2 g of 99% acetic acid were used, how many g of
ethyl acetate would be produced if the % yield were the same as in this
experiment? Show work.
22-B-6
Calculations:
1. Calculate the mass of ethanol used.
6. From the graph, determine the volume of water in the 5 L reactant mixture.
22-B-7
10. Calculate the theoretical mass of ethyl acetate that could be produced.
11. From the graph, determine the volume of water in the 5 L product mixture.
Questions:
1. What factors would cause a low yield of the ester?
3. If 1.3 g of 95% ethanol and 1.2 g of 99% acetic acid were used, how many g of ethyl
acetate would be produced if the % yield was the same as in this experiment? Show
work.
22-B-9
60 minutes
Preparations:
Time: 15 minutes
T:
T:
V:
22-B-10
Answers to questions:
1.
2.
3..
If 1.3 g of 95 % ethanol and 1.2 g of 99% acetic acid were used, how many g of
ethyl acetate would be produced if the % yield were the same as in this
experiment? Show work (numbers are left in calculator until final answer).
C2H5OH + HC2H3O2 --> CH3COOCH2CH3 + H2O
Ethanol
1.3 g x 0.95 = 1.2 g
1.2 g ethanol x 1 mol ethanol/46 g ethanol = 0.027 mole ethanol
0.027 mol ethanol x 1 mole ethyl acetate/1 mol ethanol = 0.027 mol ethyl
acetate
acetic acid
1.2 g x .99 = 1.2 g acetic acid
1.2 g acetic acid x 1 mol acetic acid/60 g acetic acid =0.020 mol acetic
acid
0.020 mol acetic acid x 1 mol ethyl acetate/1 mol acetic acid = 0.20 mol
ethyl acetate
acetic acid is limiting reagent.
22-B-11
0.20 mol ethyl acetate x 88 g ethyl acetate/1 mol ethyl acetate = 1.7 g
ethyl acetate
If the % yield = 75% the 1.74 g ethyl acetate x .75 = 1.3 g ethyl acetate
produced at a 75% yield
Considerations:
At the most it is only necessary for each group of students to run one set of
standards. If time is limited, have students share standards or run the standards before
class. Be sure to run a complete set of standards on each GC used, as results may vary
from one instrument to another. Be certain that the students understand that %
composition data obtained from the GC is not the same as % yield, since more than one
product is produced. Because of the high temperatures being used, some of the peaks
overlap and thus are not visible on the chromatograph. The pure sample injections should
have the same retention time as the corresponding component in the mixture.
22-B-12