Fisher Esterification

Elina Kvist and Amanda Josefsson

Kem022
Lucija Ostojić
2021-11-12
Aim
The purpose of this laboration is to do an esterification with an acid and an alcohol. The
synthesis is made from acetic acid and 3-methylbutane-1-ol in sulfuric acid and the product
made is a pear ester.

Theory
Fischer’s esterification is made with an alcohol and carboxylic acid and a strong acid as
catalyst. The strong acid react with the carboxylic acid wish gets protonated which starts the
reaction with the alcohol. Using an excess of the alcohol makes sure the reaction favours the
product since it is a reaction that goes both ways. When H 2 O is made and is a good leaving
group the reaction is no longer reversible. The leaving group leaves, and the oxygen double
bond is remade creating the ester.

Balanced reaction

O H2SO4
+ + H2O
HO O
OH
Figure 1:Balanced reaction of acetic acid and 3-methylbutane-1-ol forming methyl-1-buthyletanoate

1
 Mechanism

O H O H O H
O H2SO4

OH OH OH
OH

HO

H
O
H OH +
O O
H H H
OH O
H H
O O

H
H H H O
O O O
H
O H O
O O O

HO

O
+ H2O
O

2
Figure 2:Mechanism of ester reaction
Execution of experiment
The acetic acid was measured to 17.5 mL and 3-methylbutane-1-ol to 8.3 mL and added to a
round bottom flask containing a stir magnet. 1mL concentrated H 2 S O4 was added and
stirred. The solution was then heated under reflux in 1.5 hours.
After 1.5 hours the flask was cooled and then put in ice cold water. 25g of ice was added to
the solution into a beaker and stirred until the ice was melted. A separation funnel was
prepared, and the solution was added to the funnel. The beaker and round bottom flask was
washed with 2x10 mL diethyl ether and added to the funnel. 5 mL more diethyl ether was
added to the funnel and inverted for pressure release. This was done a couple of times. The
aqueous phase was then emptied in a piston. 2x15 mL of 5% N 2 C O 3was added to the organic
phase in the separation funnel. A small amount was added until 15 mL was used and the top
was closed and pressure released a couple of times. Then the aqueous phase was emptied and
the process was done one more time with 15 mL Na2 C O3 .
The organic solution was poured from the separation funnel into a beaker with MgS O 4. The
flask was weighed and then a filter paper was put into the round bottom flask. The salt was
filtered off into the flask. Then the evaporation was made using a rotary evaporator. The
sample was then weighed again.
A distiller was prepared and the solution was heated in an oil bath. The alcohol boils at
approximately 130 degrees and the product at 140-145 degrees.
Tabell 1: Chemicals used in experiment.

Chemicals M m (g) n (mol) V (mL) ρ (g/mL) equivalent

(g/mol) s
Acetic acid 60.05 18.015 0.3 17.15 1.05 1
3-methylbutane-1-ol 88.15 6.611 0.075 8.16 0.810 1
Sodiumbicarbonate 105.99 30 2.54 1
Magnesiumsulphate 120.35 2.66 -

Product
Isoamylacetate 130.19 1.69 0.013 1.92 0.88 1

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4
Calculations

Calculations of yield
Molar ratio
n(C H 3 C O2 H ) n(C 5 H 12 O) n(C 7 H 16 O 2)
= =
1 1 1
Limiting substance
Based on the calculations the limiting substance for this reaction is 3-methylbutane-1-ol
(0.075 mole).
Theoretical mass
n ( C 7 H 16 O2 )=n ( C 5 H 12 O )=0.075 mole
−1
m ( C7 H 16 O2 ) =M ( C 7 H 16 O2 ) ∙n ( C 7 H 16 O 2 )=130.19 g ∙ mol e ∙ 0.075 mole ≈ 9.76 g
Yield
Practical mass 1.69
Yield= = ≈ 0.17
Theoretical mass 9.76
The actual experiment yield 17% of the theoretical mass.

Results
When we distilled the solution and reached >130 degrees the alcohol was supposed to stop
dropping into the waste flask until 140-145 degrees was reached. The dripping did not pause
and when reaching the boiling point of 141.8 degrees it went very fast and the whole sample
has evaporated. We managed to switch flask at 141.8 degrees but there was only 1.69g of the
theoretical 9.915g left. This might have occurred because of too rapid heating which made it
hard to distinguish the turnover from alcohol evaporation and ester boiling point.
We also lost some sample when the pressure was too high causing some leakage.
The laboration otherwise went well with room for improvements in technique.

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Analysis

IR

Figure 3: IR results of an ester molecule

Table 1: IR interpretation

Wavelength Description
(nm)
⁓1750 nm C=O
⁓2950 nm C-H

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Questions
 Why do you extract the reaction mixture after the reaction?
After the reaction is done there is water and diethylether in the solution. By extracting
these substances, a cleaner product is left in the sample only consisting of the ester.
 What gas is made when you extract the reaction mixture with Na2CO3?
CO2 gas
 Give the reaction for the production of gas:
N a2 C O3 ( aq ) +2 C H 3 COOH ( aq ) ↔ 2C H 3 COONa ( aq )+ C O2 ( g ) + H 2 O(l)
 Why do you use H2SO4 in the reaction?
The acid is used as catalyst.

Sources
McMurry, John. Organic chemistry 9th edition. p.553.
Smith, Brian. C, “The C=O Bond, Part VI: Esters and the Rule of Three“.
Spectroscopyonline. https://www.spectroscopyonline.com/view/the-infrared-spectra-of-
polymers-iii-hydrocarbon-polymers