A.

EXPERIMENT TITLE : The Making of n-butyl Acetate

B. EXPERIMENT STARTED DATE : Wednesday, March 4th, 2020 at
07.00 am
C. EXPERIMENT FINISHED DATE : Wednesday, March 4th, 2020 at
12.00 pm
D. PURPOSE OF EXPERIMENT :
To understand the reaction of making n-butyl acetate through esterification
reaction.
E. BASIC THEORY
1. Definition of Ester
Esters are compounds that can be synthesized from the reaction
between carboxylic acid and alcohol. Esters have distinctive physical
properties that give a fragrant aroma or smell. Some esters can produce
fragrant fruits. But besides that esters can also produce aromas other than
fruits (Fessenden and Fessenden, 1986).
Esters have the general formula RCO2R' (or RCOOR'), where a
carbonyl group is bonded to an alkoxyl (-OR) group:

(Solomons and Fryhle, 2011).

Esters are commonly prepared by reaction of carboxylic acids and
alcohols in the presence of hydrochloric acid or sulfuric acid, a process
called esterification. In the reaction the hydroxyl group (OH) of the
carboxylic acid is replaced by the alkoxy group (R′O) of the alcohol.
The n-butyl acetate compound is an ester of acetic acid with n-
butanol. The compound is made through an esterification reaction with a
strong acid catalys, for example concentrated sulfuric acid.
The reverse of the esterification reaction is an example of
hydrolysis. Esters may also be obtained by reaction of acid halides or acid
anhydrides with alcohols or by reaction of salts of carboxylic acids with
alkyl halides. One ester may be converted to another ester by reaction
 (transesterified) with an alcohol, a carboxylic acid, or a third ester in the
presence of a catalys.
Esters are polar molecules, but their boiling points are lower than
carboxylic acids and alcohols with similar molecular weights because
hydrogen bonds between ester molecules are not possible.
Esters can bond hydrogen through oxygen atoms and hydrogen
atoms from water molecules. Thus, esters are slightly soluble in water.
However, because tester shells have hydrogen atoms to form a hydrogen
bond with oxygen atoms from water, they are less soluble than carboxylic
acids (Oueletter, 1994). Esters can be hydrolyzed by the influence of acids
to form alcohols and esters. The hydrolysis reaction is the opposite of
staging (Hart, 2003).
2. Nomenclature of Ester
Esters are named as if the alkyl chain from the alcohol is a
substituent. No number is assigned to this alkyl chain. This is followed by
the name of the parent chain from the carboxylic acid part of the ester with
an –e remove and replaced with the ending –oate. Example:

(methyl ethanoate) (ethyl propanoate)

Esters are formed through reactions between an acid and an alcohol
with the elimination of water. An example
 First, identify the oxygen that is part of the continuous chain and
bonded to carbon on both sides. (On one side of this oxygen there will
be a carbonyl present but on the other side there won't be)
 Second, begin numbering the carbon chains on either side of the oxygen
identified in step 1.
 Next, use this format: [alkyl on side further from the carbonyl] (space)
[alkane on the side with the carbonyl]
 Finally, change the ending of the alkane on the same side as the
carbonyl from -e to -oate.
3. Physical Properties of Ester
Esters are moderately polar, with dipole moments in the 1.5 to 2.0-
D range. Dipole–dipole attractive forces give esters higher boiling points
than hydrocarbons of similar shape and molecular weight. Because they
lack hydroxyl groups, however, ester molecules cannot form hydrogen
bonds to each other; consequently, esters have lower boiling points than
alcohols of comparable molecular weight (Carey, 2000).
Most of the esters are liquids with much lower boiling point than
those of the acids or alcohols of nearly equal weight, this is due to the
absence of the polar hydroxyl group which found in alcohols and acids and
leads to the association of the alcohol and carboxylic acid molecules with
hydrogen bonds, Esters have a neutral effect on litmus.
The boiling point of the ester is less than the boiling point of the
acid and alcohol forming it due to the absence of polar hydroxyl group
(presents in alcohols and acids) which has the ability to form hydrogen
bonds between molecules and water.
The solubility degree of ester in water is less than that of the
corresponding acid due to the absence of polar hydroxyl group (presents in
alcohols and acids) which has the ability to form hydrogen bonds between
molecules and water.
4. Chemical Properties of Ester
Hydrolysis of esters: Alcohol and acid are produced from the
hydrolysis of ester, this reaction reverse to ester formation, Hydrolysis
may take place by the use of dilute mineral acids as a catalyst and is called
acid hydrolysis, Dilute mineral acid (H+) is used to prevent the reversible
reaction.
CH3COOC2H5 + H2O → CH3COOH + C2H5OH
Hydrolysis of esters may also be carried out by heating with
aqueous alkalies, to produce the alcohol and the salt of the acid, this is
called alkaline-hydrolysis or saponification, (since soap is the sodium salt
of high carboxylic acids), NaOH is added to react with the produced acid
converting it to salt and prevent the reversible reaction.
 CH3COOC2H5 + NaOH → CH3COONa + C2H5OH
C6H5COOC2H5 + NaOH → C6H5COONa + C2H5OH
Hydrolysis of esters is the reaction of the ester with water (in an
acidic medium) to form acid and alcohol, saponification is the heating of
ester with aqueous alkalis to produce the alcohol and the salt of the acid,
Soap is the sodium salt of high fatty carboxylic acids.
The hydrolysis product of ester depends on the reaction medium
because in acidic medium, acid and alcohol are formed while in alkali
medium, salt of organic acid and alcohol are formed, Ammonolysis is the
reaction of esters with ammonia to produce acid amide and the alcohol.
CH3COOC2H5 + NH3 → CH3CONH2 + C2H5OH
C6H5COOC2H5 + NH3 → C6H5CONH2 + C2H5OH
The esterification reaction is not a neutralization reaction as it is a
reversible reaction “incomplete”, It needs a dehydrating agent, It is a slow
reaction because it takes place between molecules, water is formed due to
the combination of molecules, H from alcohol and OH from acid.
Acid + alcohol ↔ ester + H2O
The neutralization reaction is irreversible reaction “complete”, It is
a fast reaction because it takes place between ions, water is formed due to
the combination of ions H+ from acid and OH− from alkali.
Acid + base → salt + H2O
5. Esterification
Acid-catalyzed condensation of an alcohol and a carboxylic acid
yields an ester and water and is known as the Fischer esterification (Carey,
2000).
Fischer esterification is reversible, and the position of equilibrium
lies slightly to the side of products when the reactants are simple alcohols
and carboxylic acids. When the Fischer esterification is used for
preparative purposes, the position of equilibrium can be made more
favorable by using either the alcohol or the carboxylic acid in excess. In
the following example, in which an excess of the alcohol was employed,
the yield indicated is based on the carboxylic acid as the limiting reactant
(Fessenden, 1986).
An esterification product is called an ester which has a
characteristic that is fragrant. So that it is generally used as a synthetic
essence. The esterification reaction is a very slow reversible reaction. But
when using a catalyst of sulfuric acid or hydrochloric acid, the equilibrium
of the reaction will be achieved in a few hours. The esterification reaction
is basically the replacement of hydrogen in a carbonyl group with a
hydrocarbon or alkyl (Djamal, 1990).
5.1 Reaction of esterification
A carboxylic acid ester is a compound containing the –CO2R
group with R can be in the form of alkyl or aryl. An ester can be formed by
a direct reaction between a carboxylic acid and an alcohol, a reaction
called esterification. Acidic esterification is acidic and is a reversible
reaction. General reaction:
RCOOH + ROH RCOOR' + H2O (Oueletter, 1994)
The esterification reaction can take place with an acid or base
catalyst. Esters are derived from carboxylic acids. A carboxylic acid
contains the -COOH group, and in a hydrogen ester this group is replaced
by a hydrocarbon group of several types. Here we will only see cases
where the hydrogen in the -COOH group is replaced by an alkyl group,
although it is not much different if replaced with an aryl group (which is
based on a benzene ring) (Djamal, 1990).
This reaction is a reversible reaction in which Le Chatelie's
explains that the equilibrium will move towards the product (ester) when
the concentration of the reactant is added, therefore the concentration of
the carboxylic acid used is excessive. If the concentration of alcohol and
carboxylic acid 1: 1, the concentration of ester produced will be less. A
reversible reaction is a reaction that takes place in two directions, namely
an advanced reaction and a reverse reaction. While the irreversible
reaction is a reaction that goes in one direction. In the equilibrium system
the reaction is reversible (Fessenden and Fessenden, 1986).
 The esterification rate of a carboxylic acid depends mainly on the
steric obstruction in alcohol and its carboxylic acid. The acid strength of
the carboxylic acid only plays a small role in the rate of formation of esters
(Fessenden and Fessenden, 1986).
To obtain the high yield of the ester, the equilibrium must be
shifted towards the ester side. One technique for achieving this is to
overuse one of the cheap reagents. Another technique is to remove one
product from the reaction mixture (for example, by azeotropic distillation
of water) (Fessenden and Fessenden, 1986).
Especially for hydroxy carboxylic acid which has a -COOH and -
OH functional groups with certain structures it turns out that it can
undergo internal esterification under the influence of acid (H+) which after
releasing water spontaneously produces a cyclic ester called lactone. If
reacted with a base, the lactone changes to its original hydroxy acid salt
(Parlan and Wahjudi, 2003).
Reflux is the separation of a component from a substance. Basically the
principle of reflux is the same as extraction. In this method all desired
substances will end up in a solvent and all disturbing substances in other
solvents (Day and Underwood, 2002).
F. EQUIPMENTS AND MATERIALS
1. Equipments
Round bottom flask 250 mL 1 piece
Reflux condenser 1 piece
Separating funnel 1 piece
Beaker glass 100 mL 2 pieces
Oven machine 1 unit
Analytical balance 1 unit
Heating mantle 1 unit
Graduated cyllinder 50 mL 1 piece
Stative 1 piece
Clamp 1 piece
Pipette 10 pieces
Vial bottle 1 piece
Hose 3 pieces
Watch glass 1 piece
2. Materials
n-butanol 10 mL
Boiling stones 1 piece
Glacial acetic acid 30 mL
H2SO4 concentrated 3 drops
NaHCO3 saturated 7 mL
Aquades 55 mL
MgSO4 1 grams
G. PROCEDURE

n-butanol

- Measured 10 mL
- Put into 1round bottom flask
- Put 1 boiling stone
- Added little by little 3 drops of concentrated sulfuric acid
- Added 30 mL of glacial acetic acid
- Installed the reflux cooler
- Heated at temperature of 90oC-100oC for 1,5 minutes

Result

- Put the mixture into separating funnel

- Added 30 mL of water, then shaken vigorously

Top layer Bottom layer

- Added 25 mL of water
- Added 7 mL of saturated NaHCO3
then shaked
- Separated with separating funnel

Top layer Bottom layer

- Added 1grams of MgSO4 anhydrous
(which has been through the oven process)
- Filtered

Filtrate Residue
- Weighed the mass of ester

Ester mass

Reaction:
 H2SO4
 CH3COOH (aq) + CH3CH2CH2CH2OH (aq) ⇌
CH3COOCH2CH2CH2CH3 (aq) + H2O (l)
 CH3COOH (aq) + NaHCO3 (aq)  CH3COONa (aq) + H2CO3 (aq)
 H2CO3 (aq)  CO2 (g) + H2O (l)
 MgSO4 (s) + 7H2O (l)  MgSO4.7H2O (aq)
 H. RESULT OF OBSERVATION
Observation Results
No. Procedure Hypothesis/Reaction Conclusion
Before After
1.  n-butanol =  n-butanol + Reaction  n-butyl acetate
colorless solution H2SO4 = colorless CH3COOH(aq) + C4H9OH (ester) can be
H2SO4
 H2SO4 = solution (aq) ⇌ CH3CO2C4H9 (aq) made by
colorless solution  n-butanol + + H2O(l) esterification
 Glacial acetic H2SO4 + acetic by reacting
acid = acid = colorless MgSO4 + 7H2O  acetic acid with
colorless solution solution MgSO4.7H2O(aq) n-butanol and
 boiling stones =  heated = boiling H2SO4 as a
white solid  after 1,5 hours = NaHCO3(l) + catalys

 NaHCO3 = turbid solution CH3COOH(aq)   the smell of

colorless solution  after shaked = CH3COONa(aq) + H2O(l) + ester is like
 MgSO4 = separated into two CO2(g) bananas with
white solid layers colorless

 top layer = H2CO3 (aq)  CO2 (g) + solution

yellowish solution H2O (l)  the yield

 low layer = obtained is

 Observation Results
No. Procedure Hypothesis/Reaction Conclusion
Before After
colorless solution 8,2%
 after added water
+ NaHCO3 =
separated into two
layers
 after added
MgSO4 =
insoluble
 after filtered with
filter paper =
yellowish solution
 ester mass =
1,044 gr
I. ANALYSIS AND EXPLANATION
The purpose of this experiment is to know the synthesis reaction of n-
butyl acetate with esterification reaction. Estrification is a way to synthesis or
produce an ester. To synthesis an ester through esterification method, we
must react alcohol and carboxylic acid. In this experiment, we use n-butanol
as alcohol and acetic acid as carboxylic acid to produce n-butyl acetate.
The first step is measured 10 mL of n-butanol (colorless solution) using
graduated cyllinder. Then, put it into round bottom flask. n-butanol is
choosen because it has low boiling points. Then, into the round bottom flask
is added boiling stone. The purpose of the addition of boiling stones is to
distribute the heat so that the heat becomes homogeneous in all parts of the
solution. The pores in the boiling stone will help to capture air in the solution
and release it to the surface of the solution (this will cause small bubbles in
the boiling stone). Without boiling stones, the solution will be superheated in
certain parts, then suddenly will emit hot steam which can cause a burst/
explosion (bumping).
Next step is added 3 drops of H2SO4 (colorless solution) concentrated.
The addition of concentrated H2SO4 to the mixture as a catalys that increase
the rate of reaction so that the estrification reaction can run faster because
esterification reaction runs very slowly, but actually the esterification reaction
is a reversible reaction because when acetic acid and alcohol is heated it will
occur an equilibrium reaction between the ester and water. When ester and
water formed can produce reactants such as acetic acid and n-butanol again.
In other words n butyl acetate can be hydrolyzed on acid or base conditions to
produce acetic acid and n-butanol again. With the presence of concentrated
H2SO4, it can inhibit hydrolysis due to the ongoing hydrolysis reverse
reaction that is fischer esterification.
After that, added 30 mL of glacial acetic acid which is colorless and has
strong odor. Glacial acetic acid is acetic acid which does not contain water or
pure acetic acid liquid or acetic acid anhydrous. The addition of H2SO4 and
acetic acid is done in the fume hood because H2SO4 and acetic acid is a
concentrated acid. The addition of glacial acetic acid is to produce n-butyl
acetate. When carboxylic acid reacted with alcohol, they produce an ester.
The reaction is:
H2SO4
CH3COOH (aq) + CH3CH2CH2CH2OH (aq) ⇌ CH3COOCH2CH2CH2CH3
(aq) + H2O (l)
Next, assemble each equipments that use in esterification process such
as heating mantle, round bottom flask, and reflux condenser. The round
bottom flask put onto heating mantle. The heating mantle is use to heat the
solution. Then connect it with reflux condenser that pair in stative. The
function of reflux condenser is to make the solution temperature stable with
water flow from under to top, so the vapor keep cold while esterification is
ongoing. Then, let the esterification until ± 1,5 hours with temperature 90oC-
1
00oC until smell like banana. This smell is indicated that ester has been
formed. The purpose of heating process in long period of time is make the
frequency of collision between molecules increase so it can accelerate the
esterification reaction. During the heating process, the temperature must be
stable, because if the temperature low, the reaction can't run perfectly and
also the result and if to high, can caused the n-butanol will easy to evaporate.
After that, let the solution in the flask cool. Then, detached all the
equipments. And moved the solution from the flask to the separating funnel.
Be careful, closed the stopcock in the bottom and put the solution from the
top. Then, added 30 mL of water into the funnel. The function of water
addition is to separated the ester from the contaminants. Because ester has
non-polar characteristic and the contaminant has polar characteristic. The
contaminant are n-butanol and acetic acid that not reacted. Then shaked the
funnel in same direction. Be careful while shaking, after 10 times of shaking,
then open the stopcock to release the gas. Continue shaking the separating
funnel until CO2 gases are totally removed and don’t out again. After that, the
top layer is an ester. Then separate ester from residue with put round bottom
flask in vertical position, then open the stopcock to separate the residu into
beaker glass.
Then, added 25 mL of water and 7 mL of saturated NaHCO3. This
adding has purpose to separate the organic phase from water and remove the
 impurities solution. HCO3- will make bonding with H+ from acid solution amd
produce with CO2 gases and H2O as this reaction:
CH3COOH (aq) + NaHCO3 (aq)  CH3COONa (aq) + H2CO3 (aq)
H2CO3 (aq)  CO2 (g) + H2O (l)
Shake the funnel with same method like before until CO2 gas has gone
from the solution and put it in vertical position then separated by opening the
stopcock so that the bottom layer will separated with the top layer which is an
ester (yellowish solution) that has been formed. Move the ester from the
separating funnel to the beaker glass
The next step is added 1 grams of MgSO4 which has been put into oven
machine before. So that the water content is gone and the MgSO4 become
MgSO4 anhydrous. The function of the addition MgSO4 anhydrous is to
reduce the water content from the ester because MgSO4 anhydrous will bind
the H2O. The reaction is:
MgSO4 (s) + 7H2O (l)  MgSO4.7H2O (aq)
Then from the beaker glass which contain mixture of ester and MgSO4
anhydrous filtered with filter paper. Then the filtrate is weighed as ester mass.
And from the calculation the mass of ester is 1,044 grams and the rendement
is 8,2%.
J. CONCLUSION
Based on experiment that we have done, we can conclude that:
1. The esterification making can produce from n-butanol and glacial acetic
acid with H2SO4 solution as the catalys. The esterification is the reaction
process that need more time to get ester as the organic compound with
stable temperature.
2. The ester solution has properties brownish yellow and smell like banana.
3. Mass of the ester is 1,044 gram with precentage of rendement is 8,2%
K. REFERENCES
Carey, F. A. 2000. Organic chemistry 4th ed. USA: McGraw-Hill
Day R, A., dan Underwood A,L. 2002. Analisis Kimia Kuantitatif. Jakarta:
Erlangga.
Djamal, Rusdi. 1990. Kimia Bahan Alam. Padang: Universitas Andalas
Fessenden, R. J., & Fessenden, J. S. 1992. Kimia Organik, Edisi ketiga. Jakarta:
Erlangga
Hart, Harold. 2003. Kimia Organik. Jakarta: Penerbit Erlangga
Ouelette, Robert J. 1995. Organic Chemistry. New York: Mac Millan
Publishing Company
Parlan dan wahjudi. 2003. Kimia Organik I. Malang: Jurusan Kimia FMIPA
Universitas Negeri Malang
Solomons, T. W. G. and Fryhle, C. B. 2011. Organic Chemistry, 10th ed. New
Jersey: John Wiley & Sons, Inc
L. ATTACHMENTS
a. Documentation
Procedure Picture Explanation
10 ml of n-butanol
n-butanol
colorless solution is
- Put 10 ml of n-butanol put into a flask and
into a round bottom also put 1 boiling
flask stone
- Put 1 boiling stones
- Added 30 ml of glacial
acetic acid 30 ml of glacial acetic
- Installed the reflux acid were added
cooler
- Heated the mixture at
a temperature of 90°C-
100°C

result added 5 drops of

concentrated H2SO4
solution

Installed on
reflux. And heated for
1.5 hours
result The mixture for 1.5
hours for heating turns
- Putted the into a turbid white
reaction mixture solution
in the separating
funnel
- Added 30 ml of
water, then
beateng vigorously
The reaction product
solvent
is put into a separating
funnel, added with 30
ml of water and
(solvent) Low
shaken 15 times and
top layer layer,
water
the faucet is opened
occasionally to
remove the formed
gas.
Obtained a solution to
form 2 layers. The top
layer of the solution is
yellowish. The lower
layer of the solution is
colorless.

After removing it from

the separating
funnel. A comparison
is made between the
top layer (solvent) and
the bottom layer. The
top layer of the
solution is yellowish,
the lower layer of the
solution is colorless.
(solvent) top layer Solvent plus 25 ml of
water and 7 ml
- Added 25 ml of of concentrated
water
NaHCO3 , then put
- Added 7 ml of
into a separating
saturated
NaHCO3, then funnel, shake
shake well. Then form 2
- Separated ester layers. The top layer
layer with of the solution is faded
separating funnel yellow, the lower
layer of the solution is
colorless
(solvent) Low The top layer (solvent)
top layer, layer, is removed from the
ester water separating funnel

weighed anhydrous
MgSO4 (white crystal
solid) of 1 gram.

Anhydrous MgSO 4 is
put into the solvent.
Weighed empty
beaker. the weight of
the beaker is 27.0688
gram.

After
adding anhydrous
MgSO4 then
filtered. And the
filtrate (ester) is
obtained.

Weighed beaker and

filtered ester. Obtained
chemical weight +
ester weight 28.1128
grams.
Esther weight of 1,004
grams.
b. Answer of Question
1. What is the function of sulfuric acid, and can it be replaced with other
acids? Explain!
Answer:
The function of concentrated sulfuric acid (H2SO4) is as a catalyst to
decrease the activation energy so that the reaction equilibrium will
occur more quickly. Sulfuric acid (H2SO4) can be replaced with other
acids, provided that the catalyst is prepared from strong acids such as
hydrochloric acid (HCl).
2. Explain why the ester layer is above!
Answer:
It is because ester (n-butyl acetate) has non polar properties while water
has polar properties and the density of ester is smaller than density of
water which is underneath, so that is caused the ester layer is in above
and the water layer is in bottom.
3. Explain the function of adding saturated NaHCO3 solution and
anhydrous MgSO4!
Answer:
 The function of NaHCO3 is to bind excessive reconstitution and
neutralize the acidic solutions that are still present in the organic
phase.
 The function of MgSO4 is to bind or remove water left in the ester
4. Mention other chemicals that can be used instead of MgSO4!
Answer:
The chemical that can be used instead MgSO4 must be chemical that
include anhydrate compounds, such as CaSO4. xH2O, CaCl2. x H2O, or
NaSO4. xH2O
c. Calculation
 Mass of n-butanol = 10 mL x 0,81 gr/mL =8,1 gram
 Molecule weight of C4H9OH = 4(12) + 9(10) + 1(16) = 74 gr/mol
 Mole of n-butanol = = 0,109 mol

 Mass of CH3COOH = 30 mL x 1,05 gr/mL = 31,5 gram

 Molecule weight of CH3COOH = 2(12) + 4(1) + 2(16) = 60 gr/mol

 Mole of CH3COOH = = 0,525 mol

CH3COOH + C4H9OH ⇌ CH3COOCH2CH2CH2CH3 + H2O

M 0,525 mol 0,109 mol - -
R 0,109 mol 0,109 mol 0,109 mol 0,109 mol
S 0,416 mol - 0,109 mol 0,109 mol

MW of n-butyl acetate = 6(12) + 12(1) + 2(16) = 116 gr/mol

Mass theory of ester = 0,109 mol x 116 gr/mol = 12,644 gram
Ester mass = Mass of ester and beaker glass - mass of beaker glass
= 28,1128 gr - 27,0638 gr = 1,044 gram

Rendement mass = x 100% = x 100% = 8,2%