Experiment 4 : Organic Synthesis: Formation of Ester

SUMMARY

The objective of this experiment is to synthesis the ethyl acetate (ethyl ethanoate). The weight of
the product was 40.04g and the percentage yield calculated and it was 51.98%. Percentage yield
can be calculated by finding the actual yield and the theoretical yield. The value of theoretical
yield should be higher than the value of the actual yield. In this experiment, the theoretical yield
calculated was higher than the actual yield. This experiment considered as successful as the
actual yield was within the value of theoretical yield calculated. Two samples were taken using
the Transform Infrared Spectroscopy (FTIR) which was the standard and sample solution in
order to make a comparison. Based on the results obtained, we can see the peaks were below
3000 cm-1 which indicates that the molecule is saturated. The value of peak shown was 2984.03
cm-1 and this has proven that esters are present in the molecule. Based on the result, the retention
time for standard is 0.300min while for sample is 0.371 min. The retention time compared was
quite close and it is safe to say that both molecules were ethyl acetate because the difference
between the retention times is not that obvious. While running this experiment, this experiment
was to be cautious with the concentrated sulphuric acid which is burning and unsafe. From that
point forward, don’t put excessively hostile to knocking granules as it may influence the result of
the trial and bother the response among liquor and carboxylic acid.

OBJECTIVE

 • To synthesis ethyl acetate (ethyl ethanoate)

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INTRODUCTION

In chemical engineering or in chemical subject, there is a chemical compound named esters.

Esters are derived from an acid (organic or inorganic) in which at least one –OH (hydroxyl)
group is replaced by an alkyl group. Usually, esters are derived from a carboxylic acid and
alcohol. Esters with low molecular weight are commonly used as fragrances and found in
essential oils too. Esters used in fragrances because it can produce a really good smell.

Esters are a group of organic compounds best known for their interesting odors and flavors.
Many natural odors and flavors were discovered to be esters and therefore, many synthesized
esters are used in perfumes and foods. Chemist use organic synthesis to make larger amounts of
useful natural compounds and to invent totally new compounds. Depending on the choice of R’
and R, we have variety of the final ester, R’COOR. Small chain side groups give very aromatic
compound, while long chain side groups form waxy compounds. We can write a general
equation for the formation of esters as follows:

The reaction of carboxylic acid with an alcohol to produce an ester plus water is known as Fisher
esterification reaction. A mineral acid, usually sulphuric acid is used as a catalyst. The reaction
between the alcohol and acid is rather slow at room temperature. In order to speed it up and get
an appreciable yield in the time available, you will use a temperature of about 100°C and add
sulfuric acid to act as a catalyst in the reaction.

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MATERIALS

Chemical - Ethanol, glacial acetic acid, conc. sulfuric acid, 30% sodium carbonate solution, calcium
chloride , granular anhydrous calcium chloride, anti-bumping granules.

Apparatus - Round bottom flask, water condenser, retort stand, separating funnel

PROCEDURES

1. The reflux system is set up.

2. 50 ml of 95% ethanol is mixed with 50 ml of glacial acetic acid and poured into 250 ml round –
bottomed flask. Then 10 ml of concentrated H2SO4 is added slowly and the mixture is ensured to
be homogenous. The flask is fitted with a reflux water condenser and the mixture is boiled for 10
minutes. After that, the flask is cooled.
3. Few boiling chips are placed in the flask. A receiver is used it was a filter flask, whose side arm is
joined to a rubber tube leading over the edge of laboratory bench.
4. The distillate is transferred to a separating funnel and 25 ml of 30 % Na2CO3 solution is added.
The mixture is shaken and the stopcock is opened time by time by hearing the hissing sound. Two
layers will be separated. The lower layer is rejected and the we have to ensure that the sodium
carbonate is removed as completely as possible.
5. 25 g of calcium chloride in 25 ml of water is prepared and crude ethyl acetate is added into the
funnel. The mixture is shaken and the mixture is allowed to separated into 2 layers. The lower
layer is removed as complete as possible.
6. a few lumps of granular anhydrous calcium chloride are added into the ethyl acetate and the
mixture is shaken until liquid is clear.
7. For distillation, the temperature is arranged from 0 – 100 °C. the receiving flask is weighed first.
The distilling flask should be placed in cold water bath, which is gradually heated.
8. The ether that is always formed in this reaction will distill off at 35 – 45 °C and may be
discarded. Heat process continued and the fraction is collected.

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9. The product is weighed and the percentage yield is calculated.
10. FTIR is run to characterize the smell.
11. The substrate and product are injected into gas chromatography.

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RESULTS (ANALYSIS)

1. From mass of acid, determine the percent yield of your final product.

Actual
Percent Yield= ×100 %
Theoretical

CH3CH2OH + CH3COOH CH3COOCH2CH3 + H2O

Actual mass of ethyl acetate = 40.04 g

Theoretical value calculation:

Acetic acid density = 1.05 g/cm3

mass , g
Density , ρ=
volume , cm3

g mass , g
1.05 3
=
cm 50 cm3

Mass , g=52.5 g

1 mol CH 3 COOH 1 mol C 4 H 8 O 2 88.11 g C 4 H 8 O 2

52.5 gCH 3 COOH × × ×
60.05 g CH 3 COOH 1 mol CH 3 COOH 1 mol C 4 H 8 O 2

Theoretical value: 77.032 g

Percent yield:

40.04 g
× 100 %=51.98 %
77.03 g

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 2. Interpret the FTIR of this compounds. Identify the principle peaks.

Solution Peak value (cm-1)

Standard 3472.96
Sample 2984.03

3. Interpret gas chromatography results.

Solution Retention time (min)

Standard 0.371
Sample 0.300

Discussion

Esterification is the term used to synthesize ester through a chemical reaction in which two
reactant (usually a hydroxyl compound and an acid) is reacted. There a many ways of
esterification but in this experiment, the Fischer esterification method used due to its compound
availability. It involves treating a carboxylic acid with an excess alcohol in presence of a
dehydrating agent(which in this case is sulfuric acid, H2SO4). Weaker acids can also be used in
case of unavailability of H2SO4 but with a consequence of a longer reaction time. The reason
excess alcohol and a dehydrating agent is used to improve/increase yield of ester since
esterification is highly reversible. Dehydrating agent is basically a catalysts that is used to
catalyze the reaction. The purpose of using a boiling chip/stone is to make them boil more
calmly evading flash boiling. Actual mass of ethyl acetate weigh 40.04 grams compared to the
theoretical mass of ethyl acetate 77.032 grams. In addition, the actual mass is divided with the
theoretical mass times with 100% justifying percentage yield of 51.98% of this experiment
which is about more than half of theoretically.

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Pre – Lab Question

1. Reaction of acetic acid with ethanol to produce will produce ethyl ethanoate and water. Based on that
the reaction, how many grams of ethyl ethanoate would be produced if 50 ml of ethanol were reacted with
50 ml acetic acid? (given U ethanol: 0.8 g/ml and U acetic acid: 1.06 g/ml and U ethyl acetate: 0.9g/ml).
Calculate the percentage yield if 50.0 g of ethyl ethanoate was obtained from the experiment.

C2H5OH (aq) + CH3COOH (aq) --> CH3COOC2H5 (aq) + H20 (l)

 Moles for C2H5OH = 0.868 mol

g
0.8 x 50 ml = 40 g
ml

1 mol
x 40 g = 0.868 mol
46.07 g

 Moles for CH3COOH = 0.883 mol

g
1.06 x 50 ml = 53 g
ml

1 mol
x 53 g = 0.883 mol
60.05 g

 Mass of ethyl ethanoate

g
0.868 mol x 88.11 = 76.48 g
mol

 Percentage yield

actual
% yield = x 100%
theoritical

= 50/76.48 x 100

= 65.38 %

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Post – Lab Question

1. What are percent yields? How this can be improves?

Percent yield is the percent ratio of actual yield to the theoretical yield. It is calculated to be the

experimental yield divided by theoretical yield multiplied by 100%. To obtain more improved yield, we
must use clean glassware. Any contamination will affect the reactions. Next, we have to calculate and
weigh reagent amounts accurately. Different readings of weight affect the calculation. Next, purify
reagents and solvents if necessary. After that, rinse (3 times with reaction solvent) flasks and syringes
used to transfer reactant and reagents.

2. Based on result above, does the FTIR show any contaminant from initial reactants? Explain.

From the results, the standard peak value is 3472.96 cm -1 meanwhile the sample solution peak value is
2984.03 cm-1. The concept of contamination is about the presence of other unwanted substance in the
solution. This machine will detect any presence of substance and marks the peak. From this way, we
know that there are contaminations in the solution prepared. It is particularly will detect the functional
group of an organic compound due to the vibrations or the rotations.

Conclusion and Recommendation

An experiment was led to combination ethyl acetic acid derivation (ethyl ethanoate).The
reason among alcohol and carboxylic acid known as fisher esterification respond with the
assistance of sulphuric acid as a catalyst to create ester and water. This esxperiment utilized cold
acidic corrosive and 95 % ethanol as reactants with the mixture of H2SO4, Na2CO3 and CaCI to
create ester. Against knocking granules was utilized to make the arrangement bubble smoothly.
The heaviness of the item was taken so as to ascertain the rate yield. The aggregate mass of the
item is 40.04 g and the level of the yield of this item is 51.98%. The smell of this item isn't so
fragrant yet it appear to be a nail clean remover. This item was controlled by FTIR and a while
later it was infused into gas chromatography to interpret the important principle of the diagram
and to get the retention time.

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 The recommendation of this experiment was to be cautious with the concentrated sulphuric
acid which is burning and unsafe. The response ought to most likely be done in an answer of
phosphoric acid with a catalytic measure of sulphuric acid. The acid wasn't there to protonate the
acetic acid derivation particles. The corrosive will enact the carbonyl of the acidic carbonyl by
protonating the carbonyl oxygen. This expands the electrophilicity of the carbonyl carbon,
making it more succeptible to nucleophilic assault by the ethanol. From that point forward, don't
put excessively hostile to knocking granules as it may influence the result of the trial and bother
the response among liquor and carboxylic acid. The last item ought to be refined again to isolate
the result of the ester which is water. The water makes the immaculateness of the ester diminish.
At long last, the example ought not be presented to the air before infusing it into gas
chromatography since it may influence top area of the graph.