A.

EXPERIMENT TITTLE : Hydrolysis of Ethyl Acetate

B. EXPERIMENT START : Monday, 14th October 2019 at 01.00 p.m
C. EXPERIMENT FINISH : Monday, 14th October 2019 at 03.30 p.m
D. EXPERIMENT PURPOSE :
Determine orde reaction and ethyl acetate hydrolysis in weak acid and
strong acid
E. BASIC THEORY
a) Hydrolysis of Ethyl Acetate
Hydrolysis is the chemical decomposition involving the breaking of ester
bond and releasing the fatty acid and glycerol in the presence of an alkali.
Hydrolysis can also be defined as a chemical decomposition involving
breaking of a bond and the addition of elements of water. The use of an acid
catalyst accelerates the hydrolysis. The reaction rate is expressed in terms of
chemical composition of the reacting species (Octave, 2008). Hydrolysis is a
chemical reaction that breaks down water molecules (H2O) into hydrogen
cations (H+) and hydroxide anions (OH-) through a chemical process.
Hydrolysis can also be defined as a breakdown of salt in water that produces
acids or bases. Besides hydrolysis can also be interpreted as a reaction between
compounds and water that forms an equilibrium reaction. The compounds used
can be either organic or inorganic compounds. In the process of hydrolysis, salt
will be decomposed by water to produce a solution that is acidic or basic. The
equation for the reaction in the hydrolysis of ethyl acetate is:

The hydrolysis process is influenced by several factors namely pH,

temperature, and catalyst concentration (Sari, 2009), namely:
 pH (degree of acidity)
pH affects the hydrolysis process so that hydrolysis can be produced as
desired, a good pH for the hydrolysis process is 2.3.
 Temperature

1
 Temperature also affects the speed of the hydrolysis reaction process, a
good temperature for cellulose hydrolysis is around 21oC.
 Concentration
Concentration affects the rate of hydrolysis reaction, for acid hydrolysis
used concentrated HCl concentrations or concentrated H2SO4 (Groggins,
1985).

The hydrolysis of ethyl acetate is a reversible reaction that is not only the
reactants that react to form the product but the product also reacts with each
other to form reactants again and takes place in a balance that is the rate of
product formation equal to the rate of product decomposition. In equilibrium is
known as the equilibrium shift where the rate of product formation or the rate
of decomposition of the product can be regulated. In the hydrolysis of ethyl
acetate, excess water is used because excess water will shift the equilibrium
toward carboxylic acid. Water will attack the carbonyl group. RO bond will
not break in the hydrolysis reaction because the hydrolysis reaction is a reverse
reaction from esterification or ester-making reaction where in the esterification
used excessive amounts of alcohol .

b) Ethyl Acetate

Ethyl acetate is an organic compound with the formula CH3CH2OC (O)

CH3 or CH3COOC2H5. Ethyl acetate is a polar solvent that is volatile (non-
volatile), non-toxic, and not hygroscopic. Ethyl acetate is the recipient of
hydrogen bonds because of the presence of acidic protons (ie hydrogen bound
to electronegative electrons such as Fluorine, Oxygen, and Nitrogen). Ethyl
acetate can dissolve water up to 30% and dissolve in water up to 8% solubility
at room temperature. Its solubility increases at high temperatures. However,
this compound is unstable in water containing acids or bases (Fessenden,
1982).

Ethyl acetate can be hydrolyzed under acid or base conditions produce

acetic acid and ethanol again. Acid catalysts such as sulfuric acid can inhibit
hydrolysis because the reverse hydrolysis reaction takes place, namely Fischer

2
esterification. The fischer esterification process is a reaction between
carboxylic acid and alcohol. The carboxylic acid used is acetic acid
(CH3COOH) and the alcohol used is methanol (CH3OH). The volume of
NaOH used is different. When hydrolyzing using acetic acid the volume of
NaOH needed is only a little because in the hydrolysis of ethyl acetate the
result is acetic acid and ethanol, thus affecting the reaction speed of the
hydrolysis, the volume of NaOH used is only small. While hydrolysis using
HCl requires a large volume of NaOH because it is needed to neutralize the
HCl first. Here HCl and astetic acid act as catalysts. (Wilkinson, 1975). To
obtain a high yield ratio, strong bases with stoichiometric proportions are
usually used, for example sodium hydroxide (Laidler, 1965). This reaction
produces ethanol and sodium acetate, which cannot react anymore with
ethanol. The reaction equation is:

1. Hidrolisis Etil Asetat dalam Suasana Asam Lemah

 CH3 COOH (aq) + H2 O (l) → CH3 COOH (aq)
H+
 CH3 COOC2 H5 (aq) + H2 O (l) → CH3 COOH (aq) +
C2 H5 OH (aq)
 CH3 COOH (aq) + NaOH (aq) → CH3 COONa (aq) + H2 O (l)
2. Hidrolisis Etil Asetat dalam Suasana Asam Kuat
 HCl (aq) + H2 O (l) → HCl (aq)
H+
 CH3 COOC2 H5 (aq) + H2 O (l) → CH3 COOH (aq) +
C2 H5 OH (aq)
 HCl (aq) + NaOH (aq) → NaCl (aq) + H2 O (l)

Characteristic of Ethyl Acetate :

- Acidity: Hydrogen (H) atoms in the carboxyl group (−COOH) in carboxylic
acids such as acetic acid can be released as H+ (proton) ions, giving them
acidic properties. Acetic acid is a monoprotic weak acid with a pKa = 4.8. The
conjugate base is acetate (CH3COO−). A 1.0 M solution of acetic acid
(approximately equal to the concentration in house vinegar) has a pH of
around 2.4.

3
- Cyclic Dimers : The crystalline structure of acetic acid shows that the acetic
acid molecules pair up to form dimers connected by hydrogen bonds. Dimers
can also be detected in steam at 120 °C. Dimers also occur in dilute solutions
in non-hydrogen-bound solvents, and sometimes in pure acetic acid liquids.
The polymer is damaged in the presence of hydrogen-bound solvents (for
example water). The enthalpy of the dimer dissociation is estimated to be
65.0-66.0 kJ / mol, the dissociation entropy of about 154–157 J mol–1 K–1.
This dimerization property is also shared by other simple carboxylic acids.
- As a Solvent: Liquid acetic acid is a hydrophilic (polar) protic solvent, similar
to water and ethanol. Acetic acid has a moderate dielectric constant, 6.2, so
acetic acid can dissolve both polar compounds such as inorganic salts and
sugars as well as non-polar compounds such as oil and elements such as sulfur
and iodine. Acetic acid splashes easily with other polar or nonpolar solvents
such as water, chloroform and hexane. The solubility and ease of mixing of
acetic acid make it widely used in the chemical industry.
- Chemical Reactions : Acetic acid is corrosive to many metals such as iron,
magnesium and zinc, forming hydrogen gas and acetate salts (called metal
acetate). Metal acetate can also be obtained by the reaction of acetic acid with
a suitable base. A famous example is the reaction of baking soda (Sodium
bicarbonate) to react with vinegar. Remove all acetate salts that dissolve well
in water. One exception is chromium (II) acetate. Examples of acetate salt
formation reactions:
Mg(s) + 2 CH3COOH(aq) → (CH3COO)2Mg(aq) + H2(g)
NaHCO3(s) + CH3COOH(aq) → CH3COONa(aq) + CO2(g) + H2O(l)
Two typical organic reactions of acetic acid Acetic acid undergoes
carboxylic acid reactions, for example producing acetic salt when it reacts
with alkalis, producing ethanoate metal when reacting with metals, and
producing ethanoate metal, water and carbon dioxide when reacting with
carbonic or bicarbonate salts. The best-known organic reaction of acetic acid
is the formation of ethanol through reduction, the formation of carboxylic
acid derivatives such as acetyl chloride or acetic anhydride through
nucleophilic substitution. Acetic anhydride is formed by condensation of two

4
 molecules of acetic acid. Esters of acetic acid can be obtained through the
Fischer esterification reaction, and also the formation of amides. At 440 °C,
acetic acid breaks down into methane and carbon dioxide, or ketene and
water.
- Detection : Acetic acid can be recognized by its distinctive smell. In addition,
salts of acetic acid react with iron (III) chloride solution, which produces a
deep red color that disappears when the solution is acidified. Acetate salts
when heated with arsenic trioxide (AsO3) form kakodil oxide ((CH3)2As-O-
As(CH3)2), which is easily recognized by its unpleasant odor.
c) Reaction rate
The rate of reaction is defined as the change in the number of molecules of
reacting species per unit volume per unit time. It is also defined to be
proportional to the concentration of reacting species raised to a certain power
called the order of reaction. It is usually taken as the rate at which the reactant
disappear or the rate at which the product is formed. The rate at which the
reactant ‘a’ is disappearing is proportional to its concentration at any instance
(Dara, 2009).
rate (r) α (a - x)
rate (r) = k (a - x)
Which is, k = rate constant (Fogler, 2008)
The reaction rate per unit volume is a function of concentration: reactants,
sometimes products and even reagents that do not appear in the equation for
the whole reaction (Wilkinson,1980)
aA + bB + .....= pP + qQ + .......
simple form:
−1 𝑑[𝐴] 1 𝑑[𝑃]
𝑟= = = = 𝑘 [𝐴]𝛼 [𝐵]𝛽 [𝐶]𝛾
𝛼 𝑑𝑡 𝑃 𝑑𝑡
𝑛= 𝛼+ 𝛽+ 𝛾
To calculate the reaction rate if concentration data are obtained, then the
integral method can be used both graphically and non-graphically. With the
non-graphical method, the rate constants (k) of several orders can be
determined by trial and error. The adjacent k values indicate the corresponding
order. As for the graph method, the corresponding order is known with a linear

5
regression value close to 1. In theory, the hydrolysis rate of ethyl acetate has
the order of 2. That is, each addition of the reactant concentration is 2 times the
original, then the rate will increase to 22 times the original rate, and so so on
for the addition of reactants by n times. The law of reaction rates for order 2 is:
dx
= k(a − x)(b − x)
dt
a = initial concentration (mol / L)
b = initial concentration OH- (mol / L)
x = concentration of ester or base (M)
k = reaction rate constant
(Wilkinson, 1980)
The law of reaction rate (The Rate Law) shows the correlation between
reaction rate (V) of the concentration of the reaction rate (k) and the reactant
concentration raised by a certain number (reaction order). The law of reaction
rates can be stated as follows: aA + Bb Cc + Dd
v = k [A]x [B]y
x and y are rank numbers (reaction order) which can only be determined
through experimentation. Both x and y values are not the same as the reaction
coefficients a and b. The digits x and y show the effect of the reactants A and B
concentrations on the reaction rate. The total order (overall order) or reaction
rate is the total number of reactant reaction orders. In this case, the total order
is x + y.
The reaction rate according to first order, where n = 1 is influenced by the
concentration of the reactants where the reaction rate is directly proportional to
the concentration of the reactants. This means that increasing the concentration
will also increase the rate of reaction (Labuza, 1982). In zero-order reactions,
where n = 0 the rate of the reaction does not depend on the concentration of the
reagent and is constant at a constant temperature. Thus, the rate of zero-order
reactions depends only on the reaction rate constant (k). The reaction order is
the base of concentration in the rate law. To be able to determine whether or
not a second order reaction can be investigated as in a first level reaction,
namely:
1. By entering prices a, b, t and x in the equation:

6
 1 ba  x 
k2  ln
t(a  b) a b  x 

If the prices of k2 are fixed then the second order reaction.

2. Grapically
2,303 ba  x  2,303 b
t log  log
k 2 a  b  a b  x  k 2 a  b  a

If the second order reaction then the graph t to log a  x  is a straight line
b  x 
tangent or slope:
2,303
slope 
k 2 a  b 
2,303
k2 
slope a  b 

For the same concentration:

1 1
k2  
ax a
1 1
t 
k 2 a  b  k 2 a
1
So the graphic is must be straight if the second order reaction.
ax

Integral graph method

The order of a reaction can be determined by making a graph from

experimental data. For Order 2 applies:

Non-Graph Integral Method

7
 For orde 2:
𝑑𝑥 𝑑𝑥
= 𝑘(𝑎 − 𝑥)2(𝑎−𝑥)2 = 𝑘 𝑑𝑡
𝑑𝑡

𝑑𝑥
−∫ = 𝑘 ∫ 𝑑𝑡
(𝑎 − 𝑥)2
1
=𝑘𝑡+𝐶
(𝑎 − 𝑥)
When t = 0 dan x = 0
1
= 𝑘0+𝐶
(𝑎 − 0)
1
=𝐶
𝑎
So :
1 1
=𝑘𝑡+
(𝑎 − 𝑥) 𝑎
𝑥
kt =
𝑎(𝑎−𝑥)

F. TOOLS AND MATERIALS

 Tools
1. Erlenmeyer flask 6 pieces
2. Graduated cylinder 10 ml 1 piece
3. Graduated cylinder 50 ml 2 pieces
4. Stopwatch 1 piece
5. Beaker glass 400 ml 2 pieces
6. Pipete 5 pieces
7. Buret 1 piece
8. Statif and klem 1 set
 Materials
1. NaOH solution sufficiently
2. CH3COOC2H5 solution 40 ml
3. CH3COOH 0,5 M solution 50 ml
4. HCl 0,5 M solution 50 ml
5. Cool aquadest 600 ml
6. PP indicators 24 drops

8
G. LANES WORK
1) Hydrolysis of ethyl acetate in weak acid

50 ml acetic acid 0,5 M +

45 ml aquadest

- Entered into erlenmeyer A

- Let in room temperature for
15 minutes

Acetic acid solution

Reaction:
CH3COOH (aq) + H2O (l)  CH3COOH (aq)

50 ml ethyl acetate

- Entered into erlenmeyer B

- Let in room temperature for
15 minutes

Ethyl acetate solution

Reaction:

H+
CH3COOC2H5 (aq) + H2O (l)  C2H5OH (aq) + CH3COOH (aq

9
 5 ml ethyl acetate solution

- Poured into erlenmeyer A

- Stirred

Mixed solution

- Let in room temperature for

5 minutes
- Taken 10 ml mi
- Entered into erlenmeyer C
contain of 50 ml cool
aquadest
- Titrated with NaOH
- Repetaed with range of 10,
20, 30, 50, and 60 minutes

Volume NaOH

Reaction:
CH3COOH (aq) + NaOH (aq)  CH3COONa (aq) + H2O (l)

2) Hydrolysis of ethyl acetate in strong acid

50 ml HCl 0,5 M + 45 ml
aquadest

- Entered into erlenmeyer A

- Let in room temperature for
15 minutes

HCl solution

Reaction:
HCl (aq) + H2O (l)  HCl (aq)

10
 50 ml ethyl acetate

- Entered into erlenmeyer B

- Let in room temperature for
15 minutes

Ethyl acetate solution

Reaction:

H+
CH3COOC2H5 (aq) + H2O (l)  C2H5OH (aq) + CH3COOH (aq)

5 ml ethyl acetate solution

- Poured into erlenmeyer A

- Stirred

Mixed solution

- Let in room temperature for

5 minutes
- Taken 10 ml mi
- Entered into erlenmeyer C
contain of 50 ml cool
aquadest
- Titrated with NaOH
- Repetaed with range of 10,
20, 30, 50, and 60 minutes

Volume NaOH

Reaction:
HCl (aq) + NaOH (aq)  NaCl (aq) + H2O (l)

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G. OBSERVATION RESULT

Observation Result
No. Lanes Work Prediction/Reaction Conclusion
Before After
1. Hydolysis of Ethyl Acetate in Weak  Acetic acid:  Ethyl acetate  CH3COOH (aq) + The hydrolysis of
Acid colorless with for 15 H2O (l)  ethyl acetate in

50 ml acetate acid 0,5 M solution minutes: CH3COOH (aq) weak acid is second
+ 45 ml aquadest  Aquadest: colorless  CH3COOC2H 5 (aq)
order reaction using
+
H
colorless solution + H2O (l)  graph method with
- Entered into erlenmeyer A
solution  Acetate acid+ C2H5OH (aq) + R2 = 0,08653
- Let in room temperature
for 15 minutes  Cool aquadest: aquadest: CH3COOH (aq)
colorless colorless  CH3COOH (aq) +
Acetate acid solution
solution solution NaOH (aq) 
 Ethyl acetate:  Ethyl acetate + CH3COONa (aq) +
50 ml ethyl acetate
colorless acetate acid: H2O (l)
- Entered into erlenmeyer B solution colorless  The order of
- Let in room temperature  PP indicator: solution hydrolysis reaction
for 15 minutes
colorless  Ethyl acetate + is 2 (Mukhtar et al.,
Ethyl acetate solution solution with acetate acid + 2017)..

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 white blurry cool aquadest:

5 ml ethyl acetate solution colorless

solution
- Poured into erlenmeyer A  Ethyl acetate +
- Stirred
acetate acid +

Mixed solution cool aquadest +

pp indicator:
- Let in room temperature for colorless
5 minutes solution
- Taken 10 ml mi
- Entered into erlenmeyer C  Ethyl acetate +
contain of 50 ml cool acetate acid +
aquadest cool aquadest +
- Titrated with NaOH
pp indicator +
- Repetaed with range of 10,
20, 30, 50, and 60 minutes NaOH : Soft
pink solution.
Volume NaOH
 V NaOH:
5 minutes: 12,8
ml
10 minutes:

13
 13,1 ml
20 minutes:
13,2 ml
30 minutes:
13,3 ml
50 minutes:
13,4 ml
60 minutes:
13,5 ml
2. Hydolysis of Ethyl Acetate in Strong  Acetic acid:  Ethyl acetate  HCl (aq) + H2O (l) The hydrolysis of
Acid colorless with for 15  HCl (aq) ethyl acetate in

50 ml HCl 0,5 M + 45 ml solution minutes:  CH3COOC2H5 (aq) strong acid is

H+
aquadest  Aquadest: colorless + H2O (l)  second order
colorless solution C2H5OH (aq) + reaction using graph
- Entered into erlenmeyer A
solution  HCl+ aquadest: CH3COOH (aq) method with R2 =
- Let in room temperature
for 15 minutes  Cool aquadest: colorless  HCl (aq) + NaOH 0,08852
colorless solution (aq)  NaCl (aq) +
HCl solution
solution  Ethyl acetate + H2O (l)
 Ethyl acetate: HCl: colorless  The order of

14
 colorless solution hydrolysis reaction
solution  Ethyl acetate + is 2 (Mukhtar et al.,

50 ml ethyl acetate  PP indicator: HCl + cool 2017).

colorless aquadest:
- Entered into erlenmeyer B solution with colorless
- Let in room temperature
white blurry solution
for 15 minutes
 Ethyl acetate +
Ethyl acetate solution HCl + cool
aquadest + pp
indicator:
colorless
solution
 Ethyl acetate +
HCl + cool
aquadest + pp
indicator +
NaOH : Soft
pink solution.
 V NaOH:

15
 5 minutes: 12,5

5 ml ethyl acetate solution ml

10 minutes:
- Poured into erlenmeyer A 12,7 ml
- Stirred 20 minutes:
12,6 ml
Mixed solution
30 minutes:
- Let in room temperature for 12,8 ml
5 minutes 50 minutes:
- Taken 10 ml mi
12,9 ml
- Entered into erlenmeyer C
contain of 50 ml cool 60 minutes:
aquadest 13,0 ml
- Titrated with NaOH
- Repetaed with range of 10,
20, 30, 50, and 60 minutes

Volume NaOH

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H. ANALYSIS AND EXPLANATION
This experiment purpose is to determine the reaction order of hydrolysis of
ethyl acetate in weak and strong acid. The principle of this experiment, Ethyl
acetate can be hydrolyzed in acidic or basic conditions to regain acetic acid and
ethanol. In this experiment, acid is used catalyst to accelerate the hydrolysis
process of ethyl acetate.
1. Hydrolysis of Ethyl Acetate in Weak Acid
The first step was preparing acetic acid solution. 50 mL of 0,5M acetic acid
was measured using graduated cylinder, then put in Erlenmeyer A. Acetic acid is
colorless solution. Then 45 mL of aquades was measured using graduated
cylinder. Aquades is colorless solution. Next, it was entered into Erlenmeyer A
that has been filled by acetic acid before. After that it was left in temperature
room for 15 minutes. The result was colorless acetic acid solution. The reaction is:
• CH3COOH (aq) + H2O (l)  CH3COOH (aq)
Acetic acid is weak acid. In this experiment acetic acid used as catalyst to
accelerate the hydrolysis reaction of ethyl acetate. Ethyl acetate if reacted with
water, hydrolysis process will occur. The salt will be broken down by water to
produce a solution that is acidic or alkaline.
Next step was preparing ethyl acetate solution. 50 mL ethyl acetate was
measured using graduated cylinder, then put in Erlenmeyer B. Ethyl acetate is
colorless solution. After that it left in temperature room for 15 minutes. The result
was colorless ethyl acetate solution. The reaction is:
• CH3COOC2H5 (aq) + H2O (l)  C2H5OH (aq) + CH3COOH (aq)
After preparing the solution, the next step was taking 5 mL ethyl acetate
solution that has been prepared before into Erlenmeyer A, then it was stirred. The
result was colorless mixed solution. Then it was left in room temperature for 5
minutes, then it was taken 10 mL and entered into Erlenmeyer C that has been
filed by 50 mL cool aquades. The result was colorless solution. Aquades prepared
in cool condition to make the reaction slower. Next, it was added PP indicator
which is colorless. Then it was titrated with NaOH. NaOH is colorless solution.
The titration is done until the solution turns into softpink that indicates the end
point of the titration. After that, it was repeated with leaving time 10, 20, 30, 50,

17
and 60 minutes. What can be obtained from these steps is volume NaOH. From
rhe experiment, volume of NaOH needed for titration in each leaving time were:
 5 minutes: 12,8 ml
 10 minutes: 13,1 ml
 20 minutes: 13,2 ml
 30 minutes: 13,3 ml
 50 minutes: 13,4 ml
 60 minutes: 13,5 ml
The reaction of this experiment is CH3COOH (aq) + NaOH (aq)  CH3COONa
(aq) + H2O
The product produced from the reaction between ethyl acetate and water
with HCl is titrated with NaOH, The mole equivalent. of NaOH is equal to the
mole of H+ from HCl (catalyst) plus mole of H+ from the product. According to
the data and calculation, graphic and non-graphic method is used to determine the
order of the reaction.
Graphic method
Reaction order 1
t (s) ln (a-x)
300 -0.06
600 -0.13
1200 -0.15
1800 -0.17
3000 -0.19
3600 -0.2

18
 orde 1
0
0 1000 2000 3000 4000

-0.05

-0.1
ln(a-x)

ln (a-x)
-0.15 Linear (ln (a-x))

-0.2
y = -3E-05x - 0.0904
R² = 0.7786
-0.25
t (s)

Reaction order 2
t (s) 1/(a-x)
300 1.06
600 1.14
1200 1.16
1800 1.19
3000 1.22
3600 1.25

orde 2
1.3

y = 5E-05x + 1.0875
1.25 R² = 0.8653

1.2
1/(a-x)

1/(a-x)
1.15
Linear (1/(a-x))
1.1

1.05
0 1000 2000 3000 4000
time (s)

19
 The hydrolysis of ethyl acetate in weak acid is second order reaction using graph
method with R2 = 0,08653
Non-graphic method
For non-graphic method, we can see the value of the constant (k) reaction whose
range is close to constant. For reaction order 1, the formula is
ln (a-x) = ln a – k.t

t (s) ln (a-x)
300 -0.06
600 -0.13
1200 -0.15
1800 -0.17
3000 -0.19
3600 -0.2

1 1
for reaction order 2, the formula is (𝑎−𝑥) = k.t + 𝑎

t (s) 1/(a-x)
300 1.06
600 1.14
1200 1.16
1800 1.19
3000 1.22
3600 1.25

Based on the data, the order of the reaction is 2

This is in accordance with the theory that, the order of hydrolysis reaction is 2
(Mukhtar et al., 2017).
2. Hydrolysis of Ethyl Acetate in Strong Acid
The first step was preparing HCl solution. 50 mL of 0,5M HCl was
measured using graduated cylinder, then put in Erlenmeyer A. HCl is colorless
solution. Then 45 mL of aquades was measured using graduated cylinder.
Aquades is colorless solution. Next, it was entered into Erlenmeyer A that has

20
been filled by HCl before. After that it was left in temperature room for 15
minutes. The result was colorless HCl solution. The reaction is:
• HCl (aq) + H2O (l)  HCl (aq)
HCl is weak acid. In this experiment HCl is used as catalyst to accelerate the
hydrolysis reaction of ethyl acetate. Ethyl acetate if reacted with water, hydrolysis
process will occur. The salt will be broken down by water to produce a solution
that is acidic or alkaline. The product produced from the reaction between ethyl
acetate and water with HCl will be titrated with NaOH, The mole equivalent. of
NaOH is equal to the mole of H+ from HCl (catalyst) plus mole of H+ from the
product. According to the theory, a second experiment should require more NaOH
volume during titration because more moles of H+ are used in the HCl as a
catalyst than CH3COOH.
Next step was preparing ethyl acetate solution. 50 mL ethyl acetate was measured
using graduated cylinder, then put in Erlenmeyer B. Ethyl acetate is colorless
solution. After that it left in temperature room for 15 minutes. The result was
colorless ethyl acetate solution. The reaction is:
• CH3COOC2H5 (aq) + H2O (l)  C2H5OH (aq) + CH3COOH (aq)
After preparing the solution, the next step was taking 5 mL ethyl acetate solution
that has been prepared before into Erlenmeyer A, then it was stirred. The result
was colorless mixed solution. Then it was left in room temperature for 5 minutes,
then it was taken 10 mL and entered into Erlenmeyer C that has been filed by 50
mL cool aquades. The result was colorless solution. Next, it was added PP
indicator which is colorless. Then it was titrated with NaOH. NaOH is colorless
solution. The titration is done until the solution turns into softpink that indicates
the end point of the titration. After that, it was repeated with leaving time 10, 20,
30, 50, and 60 minutes. The reaction is:
• HCl (aq) + NaOH (aq)  NaCl (aq) + H2O (l)
What can be obtained from these steps is volume NaOH. From rhe experiment,
volume of NaOH needed for titration in each leaving time were:
 5 minutes: 12,5 ml
 10 minutes: 12,7 ml
 20 minutes: 12,6 ml

21
  30 minutes: 12,8 ml
 50 minutes: 12,9 ml
 60 minutes: 13,0 ml
According to the data and calculation, graphic and non-graphic method is used to
determine the order of the reaction.
Graphic method
Reaction order 1

t (s) ln (a-x)

300 0
600 -0.04
1200 -0.02
1800 -0.06
3000 -0.08
3600 -0,11

orde 1
0
300 600 1200 1800 3000 3600
-0.01
-0.02
-0.03
ln (a-x)

-0.04 y = -0.0046x - 0.0173 ln (a-x)

-0.05 R² = 0.0686
Linear (ln (a-x))
-0.06
-0.07
-0.08
-0.09
time (s)

Reaction order 2

t (s) 1/(a-x)
300 1
600 1.04
1200 1.02

22
 1800 1.06
3000 1.09
3600 1.1

orde 2
1.12
1.1 y = 0.0197x + 0.9827
R² = 0.8852
1.08
1.06
1/(a-x)

1.04
1.02 1/(a-x)
1 Linear (1/(a-x))
0.98
0.96
0.94
300 600 1200 1800 3000 3600
time (s)

The hydrolysis of ethyl acetate in strong acid is second order reaction using graph
method with R2 = 0,08852
Non-graphic method
For non-graphic method, we can see the value of the constant (k) reaction whose
range is close to constant. For reaction order 1, the formula is
ln (a-x) = ln a – k.t

t (s) ln (a-x)

300 0
600 -0.04
1200 -0.02
1800 -0.06
3000 -0.08
3600 -0,11
1 1
for reaction order 2, the formula is (𝑎−𝑥) = k.t + 𝑎

23
 t (s) 1/(a-x)
300 1
600 1.04
1200 1.02
1800 1.06
3000 1.09
3600 1.1

Based on the data, the order of the reaction is 2

This is in accordance with the theory that, the order of hydrolysis reaction is 2
(Mukhtar et al., 2017).

J. CONCLUTION

According to the experiment can be concluded:

1. The order of reaction of hydrolysis of ethyl acetate in weak acid condition
using acetic acid is 2 based on graphic method because the regression is
close to 1 and nongraphic method because the value of k is constant in
second order reaction calculation.
2. The order of reaction of hydrolysis of ethyl acetate in strong acid condition
using HCl is 2 based on graphic method because the regression is close to 1
and nongraphic method because the value of k is constant in second order
reaction calculation.

24
K. REFERENCES

Armstrong, David W., Stanley M. Martin, Hiroshi Yamazaki. 1983. Production of

Ethyl Acetate from Dillute Ethanol Solutions by Candida Utilis. Biologycal
and Engineerin, XXVI hal. 1038-1041.
Dara .2009. A Textbook of Engineering Chemistry. S. Chand and company
Limited, Ram Nagar, New Delhi. pg.845 – 862.
Fessenden, Ralp J., Fessenden, Joan S. 1982. Kimia Organik Edisi Ketiga Jilid 2
(Alih bahasa: A. Handyana Pudjaatmaka). Jakarta: Erlangga.
Fogler (2008); Elements of chemical reaction engineering, Fourth edition, Pearson
Education international, Massachusetts, USA. Pg. 4-7.
Groggins, P.H. 1985. Unit Processes in Organic Synthesis. New York :
McGrawHill Book Company Inc.
Labuza TP. 1982. Shelf-life Evaluation of Food and Nutrition. Press., Inc.,
Westport, Connecticut.
Laidler, Keith, J. 1965. Chemical Kinetics. New York: Tara M Graw-Hill
Publishing.
Mukhtar A, Shafiq U, Qazi MO, Qadir HA, Qizilbash M, Awan BA, 2017.
Kinetics of alkaline hydrolysis of ethyl acetate by conductometric
measurement approach over temperature ranges (298.15-343.15 K). Austin
Chemical Engineering, 4: 1-11.
Octave, Levenspiel. 2008. Chemical Reaction Engineering 3rd Edition.
Sari, Ni Ketut. 2009. Pembuatan Bioetanol dari Rumput Gajah dengan Distilasi
Batch. Jurnal Teknik Kimia Indonesia, 8 (3) 2009: hal. 94-103.
Wilkinson, Frank. 1975. Chemical Kinetics and Reaction Mechanisms.

25
 L. ATTACHMENT

1. Question Answer

(1) When viewed from the results of the experiment, what distinguishes
between the 3A trial and the 3B trial? Give an explanation and relate to your
library study!

Answer:

What distinguishes between hydrolysis of ethyl acetate in an

atmosphere of weak acid and strong acid is that the volume of NaOH required
in a weak acidic atmosphere is more than the volume of NaOH needed in a
strong acidic composition. This is contrary to the theory that the volume of
NaOH needed for titration in hydrolysis with strong acid conditions is more
widely used because in the atmosphere of strong acids, H+ is released more
than H+ in a weak acidic atmosphere so to neutralize it requires more
NaOH volume in the atmosphere strong acid. Underlying the incompatibility
of the data obtained with the theory is likely to be:
1. The titration process is carried out where the endpoint is observed
subjectively and the practicator is three people taking turns to do the titration
process, so that it is possible that the titration results (end points) of each
practitioner have differences that affect the NaOH volume and impact on data
precision.
2. The measurement of the time should be 5, 10, 20, 30, 50 and 60
minutes has a vulnerable that does not match expectations for example where
the first titration starts at 7:20 minutes minutes continued at
10:55 minutes, 20:57, 30:33, 50:10 and 60:20. This irregular minute
difference can affect the reaction order curve which affects the low regression
value.
3. The third factor is erroneous / inaccurate when doing a scale reading on the
burette so that it affects the NaOH (volume) value obtained.
4. Given the limited availability of equipment, the titration process is carried
out alternately with the finished equipment used to be washed first. The

26
washing process has the possibility that the washed appliance is not
100% clean. The presence of contamination in equipment used such as unclean
erlenmeyers are washed in titration with weak acid conditions reused in
titration with strong acid conditions. This affects the NaOH volume during
titration and affects the k value (if using non-graphical methods) and regression
values (if using the graph method).

27
2. Calculation

CH3COOC2H5 (aq) + H2O (l) C2H5OH (aq) + CH3COOH (aq)

5 5mL 45 mL 50 mL 100 mL
1 9 10 20
Solution taken 10 mL
1
1. Ethyl acetate = 20 𝑥 10 = 0,5 𝑚𝐿
9
2. H2O = 20 𝑥 10 = 4,5 𝑚𝐿
10
3. H+ = 20 𝑥 10 = 5 𝑚𝐿

 Mol equivalent = Vethyl acetate x Nethyl acetate

CH3COOC2H5 = 0,5 mL x 2 mmol/mL x 1 equivalent
= 1 mmol equivalent
 Mol equivalent = VH+ x NH+
CH3COOC2H5 = 5 mL x 0,5 mmol/mL x 1 equivalent
= 2,5 mmol equivalent
Reaction while titration
CH3COOH + NaOH = CH3COONa + H2O
 t=0
mmol equivalent NaOH = mmol equivalent H+
VNaOH x NNaOH = VH+ x NH+
1 equivalent x VNaOH x 0,2 mmol/mL = 5 mL x 0,5 mmol/mL x 1 equivalent
VNaOH = 12,5 mL
 t=∞
mmol equivalent NaOH = mmol equivalent H+ + mmol ethyl acetate
VNaOH x NNaOH = (VH+ x NH+) + (Vethyl x Nethyl)
1 equivalent x VNaOH x 0,2 mmol/mL = (5 x 0,5 ) + (0,5 x 2)
VNaOH = 17,5 mL

28
1. Calculation hydrolysis of ethyl aacetate in weak acid
Know :
MNaOH : 0,2 M VNaOH when = 1) t5 = 12.8 mL
MCH3COOH : 0,5 M 2) t10 = 13.1 mL
VCH3COOH : 5 mL 3) t20 = 13.2 mL
4) t30 = 13.3 mL
5) t50 = 13.4 mL
6) t60 = 13.5 mL
a) t = 5 minutes
Mmol eq NaOH = mmol eq CH3COOH (catalyst) + CH3COOH (product)
( V x N) NaOH = (V x N) catalyst + x
0,2 M x 12.8 mL= (0,5 M x 5 mL) + x
2,56 mmol = 2,5 mmol + x
x = 0.06
(a-x) = 1- 0.06
(a-x) = 0.94
b) t = 10 minutes
Mmol eq NaOH = mmol eq CH3COOH (catalyst) + CH3COOH (product)
( V x N) NaOH = (V x N) catalyst + x
0,2 M x 13,1 mL = (0,5 M x 5 mL) + x
2,62 mmol = 2,5 mmol + x
x = 0.12
(a-x) = 1- 0.12
(a-x) = 0.88
c) t = 20 minutes
Mmol eq NaOH = mmol eq CH3COOH (catalyst) + CH3COOH (product)
( V x N) NaOH = (V x N) catalyst + x
0,2 M x 13.2 mL = (0,5 M x 5 mL) + x
2,64 mmol = 2,5 mmol + x
x = 0.14
(a-x) = 1- 0.14
(a-x) = 0.86

29
 d) t = 30 minutes
Mmol eq NaOH = mmol eq CH3COOH (catalyst) + CH3COOH (product)
( V x N) NaOH = (V x N) catalyst + x
0,2 M x 13.3 mL = (0,5 M x 5 mL) + x
2,66 mmol = 2,5 mmol + x
x = 0.16
(a-x) = 1- 0.16
(a-x) = 0.84
e) t = 50 minutes
Mmol eq NaOH = mmol eq CH3COOH (catalyst) + CH3COOH (product)
( V x N) NaOH = (V x N) catalyst + x
0,2 M x 13.4 mL = (0,5 M x 5 mL) + x
2,68 mmol = 2,5 mmol + x
x = 0.18
(a-x) = 1- 0.18
(a-x) = 0.82
f) t = 60 minutes
Mmol eq NaOH = mmol eq CH3COOH (catalyst) + CH3COOH (product)
( V x N) NaOH = (V x N) catalyst + x
0,2 M x 13.5 mL = (0,5 M x 5 mL) + x
2,7 mmol = 2,5 mmol + x
x = 0.2
(a-x) = 1- 0.2
(a-x) = 0.8
 1st order reaction
a) t = 5 minutes
ln (a-x)1 = ln a – k.t
ln 0.94 = ln 1 – k.300
-0,06 = - k.300
k = 2 x 10-4
b) t = 10 minutes
ln (a-x) = ln a – k.t

30
 ln 0.88 = ln 1 – k.600
-0.13 = - k.600
k = 2.2 x 10-4
c) t = 20 minutes
ln (a-x) = ln a – k.t
ln 0.86 = ln 1 – k.1200
-0.15 = - k.1200
k = 1.3 x 10-4
d) t = 30 minutes
ln (a-x) = ln a – k.t
ln 0.84 = ln 1 – k.1800
-0.17 = - k.1800
k = 9.7 x 10-5
e) t = 50 minutes
ln (a-x) = ln a – k.t
ln 0.82 = ln 1 – k.3000
-0.19 = - k. 3000
k = -6.6 x 10-5
f) t = 60 minutes
ln (a-x) = ln a – k.t
ln 0.8 = ln 1 – k.3600
-0.2 = - k.3600
k = 6.2 x 10-5

 2nd order reaction

a) t = 5 minutes
1 1
(𝑎−𝑥)
= k.t + 𝑎
1
= k. 300 + 1
0,94

1.06 = 300.k + 1
0.66 = 300.k

31
 𝑘 = 2 x 10-4
b) t = 10 minutes
1 1
(𝑎−𝑥)
= k.t + 𝑎
1
= k. 600 + 1
0,88

1.14 = 600.k + 1
1.14 = 600.k
𝑘 = 2.3 x 10-4
c) t = 20 minutes
1 1
(𝑎−𝑥)
= k.t + 𝑎
1
= k. 1200 + 1
0,86

1.16 = 1200.k + 1
0.16 = 1200.k
𝑘 = 1.3 x 10-4
d) t = 30 minutes
1 1
(𝑎−𝑥)
= k.t + 𝑎
1
= k. 1800 + 1
0,84

1.19 = 1800.k + 1
0.19 = 1800.k
𝑘 = 1.1 x 10-4
e) t = 50 minutes
1 1
(𝑎−𝑥)
= k.t + 𝑎
1
= k. 3000 + 1
0,82

1.22 = 3000.k + 1
0.22 = 3000.k
𝑘 = 7.3 x 10-5
f) t = 60 minutes
1 1
(𝑎−𝑥)
= k.t + 𝑎
1
= k. 3600 + 1
0,8

32
 1.25 = 3600.k + 1
0.25 = 3600.k
𝑘 = 6.9 x 10-5

2. Calculation hydrolysis of ethyl acetate in strong acid

Know :
MNaOH : 0,2 M VNaOH = 1) t5 = 12.5 mL
MHCl : 0,5 M 2) t10 = 12.7 mL
VCH3COOH : 5 mL 3) t20 = 12.6 mL
4) t30 = 12.8 mL
5) t50 = 12.9 mL
6) t60 = 13.0 mL
a) t = 5 minutes
Mmol eq NaOH = mmol eq CH3COOH (catalyst) + CH3COOH (product)
( V x N) NaOH = (V x N) catalyst + x
0.2 M x 12.5 mL = (0,5 M x 5 mL) + x
2.54 mmol = 2,5 mmol + x
x =0
(a-x) = 1- 0
(a-x) =1
b) t = 10 minutes
Mmol eq NaOH = mmol eq CH3COOH (catalyst) + CH3COOH (product)
( V x N) NaOH = (V x N) catalyst + x
0,2 M x 12.7 mL = (0,5 M x 5 mL) + x
2.54 mmol = 2,5 mmol + x
x = 0.04
(a-x) = 1- 0.04
(a-x) = 0.96
c) t = 20 minutes
Mmol eq NaOH = mmol eq CH3COOH (catalyst) + CH3COOH (product)
( V x N) NaOH = (V x N) catalyst + x
0,2 M x 12.6 mL = (0,5 M x 5 mL) + x

33
 2.52 mmol = 2,5 mmol + x
x = 0.02
(a-x) = 1- 0.02
(a-x) = 0.98
d) t = 30 minutes
Mmol eq NaOH = mmol eq CH3COOH (catalyst) + CH3COOH (product)
( V x N) NaOH = (V x N) catalyst + x
0,2 M x 12.8 mL = (0,5 M x 5 mL) + x
2,56 mmol = 2,5 mmol + x
x = 0.06
(a-x) = 1- 0.06
(a-x) = 0.94
e) t = 50 minutes
Mmol eq NaOH = mmol eq CH3COOH (catalyst) + CH3COOH (product)
( V x N) NaOH = (V x N) catalyst + x
0,2 M x 12.9 mL = (0,5 M x 5 mL) + x
2,58 mmol = 2,5 mmol + x
x = 0.08
(a-x) = 1- 0.08
(a-x) = 0.92
f) t = 60 minutes
Mmol eq NaOH = mmol eq CH3COOH (catalyst) + CH3COOH (product)
( V x N) NaOH = (V x N) catalyst + x
0,2 M x 13 mL = (0,5 M x 5 mL) + x
2,6 mmol = 2,5 mmol + x
x = 0.1
(a-x) = 1- 0.1
(a-x) = 0.9

 1st order reaction

a) t = 5 minutes
ln (a-x) = ln a – k.t

34
 ln 1 = ln 1 – k.300
k =0
b) t = 10 minutes
ln (a-x) = ln a – k.t
ln 0.96 = ln 1 – k.600
-0.04 = - k.600
k = 6.8 x 10-5
c) t = 20 minutes
ln (a-x) = ln a – k.t
ln 0.98 = ln 1 – k.1200
-0.02 = - k.1200
k = 1.7 x 10-5
d) t = 30 minutes
ln (a-x) = ln a – k.t
ln 0.94 = ln 1 – k.1800
-0.06 = - k.1800
k = 3.4 x 10-5
e) t = 50 minutes
ln (a-x) = ln a – k.t
ln 0.92 = ln 1 – k.3000
-0.08 = - k. 3000
k = 2.8 x 10-5
f) t = 60 minutes
ln (a-x) = ln a – k.t
ln 0.9 = ln 1 – k.3600
-0.11 = - k.3600
k = 2.9 x 10-5

 2nd order reaction

a) t = 5 minutes
1 1
(𝑎−𝑥)
= k.t + 𝑎
1
= k. 300 + 1
1

35
 𝑘 =0
b) t = 10 minutes
1 1
(𝑎−𝑥)
= k.t + 𝑎
1
= k. 600 + 1
0,96

1.04 = 600.k + 1
0.04 = 600.k
𝑘 = 6.7 x 10-4
c) t = 20 minutes
1 1
(𝑎−𝑥)
= k.t + 𝑎
1
= k. 1200 + 1
0,98

1.02 = 1200.k + 1
0.02 = 1200.k
𝑘 = 1.7 x 10-4
d) t = 30 minutes
1 1
(𝑎−𝑥)
= k.t + 𝑎
1
= k. 1800 + 1
0,94

1.06 = 1800.k + 1
0.06 = 1800.k
𝑘 = 3.3 x 10-4
e) t = 50 minutes
1 1
(𝑎−𝑥)
= k.t + 𝑎
1
= k. 3000 + 1
0,92

1.09 = 3000.k + 1
0.09 = 3000.k
𝑘 = 3 x 10-5
f) t = 60 minutes
1 1
(𝑎−𝑥)
= k.t + 𝑎
1
= k. 3600 + 1
0,9

36
 1.1 = 3600.k + 1
0.1 = 3600.k
𝑘 = 2.8 x 10-5

3. Documentation

Lanes Result/
No. Pictures
Work Explanation
Hydrolysis of Ethyl Acetate in Weak Acid
1. Ethyl Ethyl acetate is
acetate colorless solution
preparation
for 15
minutes

2. Acetic acid Acetic acid is

preparation colorless solution

3. Acetic acid Aquadest is

added with colorless solution.
aquadest The mixture of
aquadest and acetic
acid is colorless
solution
4. Acetic acid Acetic acid is
solution colorless solution
added with and resulting
5 ml of colorless solution
ethyl
acetate

37
5. Mixture Mixture solution is
solution + colorless solution.
cool Cool aqaudest is
aquadest + colorless solution.
pp Pp indicator is
indicator colorless solution
with white blurry

6. Titration The solution

with become soft pink
NaOH in solution
range 5 V NaOH : 12,8 ml
minutes

7. Titration The solution

with become soft pink
NaOH in solution
range 10 V NaOH ; 13,1 ml
minutes

8. Titration The solution

with become soft pink
NaOH in solution
range 20 V NaOH : 13,2 ml
minutes

38
9. Titration The solution
with become soft pink
NaOH in solution
range 30 V NaOH : 13,3 ml
minutes

10. Titration The solution

with become soft pink
NaOH in solution
range 50 V NaOH: 13,4 ml
minutes

11. Titration The solution

with become soft pink
NaOH in solution
range 60 V NaOH: 13,5 ml
minutes

12. All result All resulting soft

pink solution

Hydrolysis of Ethyl Acetate in Strong Acid

39
1. Ethyl Ethyl acetate is
acetate colorless solution
preparation
for 15
minutes

2. HCl HCl si colorless

solution solution

3. HCl added Aquadest is

with colorless solution.
aquadest The mixture of
aquadest and HCl is
colorless solution

4. HCl HCl is colorless

solution solution and
added with resulting colorless
5 ml of solution
ethyl
acetate
5. Mixture Mixture solution is
solution + colorless solution.
cool Cool aqaudest is
aquadest + colorless solution.
pp Pp indicator is
indicator colorless solution
with white blurry

40
6. Titration The solution
with become soft pink
NaOH in solution
range 5 V NaOH : 12,5 ml
minutes

7. Titration The solution

with become soft pink
NaOH in solution
range 10 V NaOH ; 12,7 ml
minutes

8. Titration The solution

with become soft pink
NaOH in solution
range 20 V NaOH : 12,6 ml
minutes

9. Titration The solution

with become soft pink
NaOH in solution
range 30 V NaOH : 12,8 ml
minutes

41
10. Titration The solution
with become soft pink
NaOH in solution
range 50 V NaOH: 12,9 ml
minutes

11. Titration The solution

with become soft pink
NaOH in solution
range 60 V NaOH: 13,0 ml
minutes

12. All result All resulting soft

pink solution

42