Aayushman EE FINAL

Aayushman S. Goyal/Extended Essay/The Shri Ram School /002227-0001 1
Extended Essay
Title: Investigating the effect of ultrasound waves on the equilibrium
constant of an esterification reaction.
Research question:
How do ultrasound waves affect the value of equilibrium constants of
the esterification reactions between ethanoic acid and five different
alcohols (methanol, ethanol, propan-2-ol, butan-1-ol, pentan-2-ol) of
increasing alkyl chain lengths?
Subject: Chemistry
Session: May 2014
Candidate Name: Aayushman Sahuwala Goyal
Candidate Number: 002227-0001
School Name: The Shri Ram School, Moulsari
School Code: 002227
Supervisor Name: Dr. Sriparna Chakrabarti
Word Count: 3987 words

2 Aayushman S. Goyal/Extended Essay/The Shri Ram School /002227-0001
Abstract:
Esters are an interesting class of organic compounds for their characteristic
‘fruity odour’ and various industrial applications. A new emerging, environment-
friendly technique – sonication was used in esterification to increase the yield of
esters. My research question is: “How do ultrasound waves affect the value of
equilibrium constants of the esterification reactions between ethanoic acid
and five different alcohols (methanol, ethanol, propan-2-ol, butan-1-ol,
pentan-2-ol) of increasing alkyl chain lengths?”
I have used 1 moldm-3 of aqueous solutions of five alcohols with increasing alkyl
chain lengths (C1 to C5) and esterified with 1 moldm-3 of ethanoic acid using 1
moldm-3 of H2SO4 as catalyst. I had first conducted the esterification reactions by
heating the alcohol-carboxylic acid mixture in a water bath at 90-100°C for 30
minutes. The resultant mixtures were titrated with 1 mol dm-3 of NaOH solution.
It was observed that due to the high temperature of the water bath and the low
boiling points of some of the alcohols, the esters were not formed properly.
Hence I repeated the same experiment by refluxing the reaction mixtures for one
hour. Another set of esterification was done by using ultrasound waves of
frequency 40 kHz in an ultrasonic bath at an ambient temperature 55-60°C for
30 minutes. Also, the volume of 1 moldm-3 NaOH solution required to neutralize
1 moldm-3 H2SO4 catalyst was eliminated from the final titre values for accuracy
in the Kc values. The equilibrium constants of all these esterification reactions
were computed and compared.
I concluded that the Kc values of esterification done by sonication were
significantly higher than those done by refluxing. My hypothesis that sonication
would increase the yield of esters produced at that particular temperature was
accepted. Interestingly, refluxing gave the maximum yield of ethyl ethanoate
whereas sonication gave the maximum yield of 1-methylbutyl ethanoate.
Word Count: 299 words

Table of contents:
Heading Page no.
Introduction:
Approach to the research question
Background research
How sonicators work?
Plan of Action
4
4
6
6
7
Investigation:
Experiment 1
Experiment 2
Experiment 3
Experiment 4
10
11
15
18
22
Conclusion 25
Evaluation 27
Future Scope 27
Appendices
Appendix 1: Apparatus
Appendix 2: Detailed calculations
28
28
29
Bibliography 32
Acknowledgements 35

Introduction
Approach to the research question:
Organic chemistry is the science of designing, synthesizing, and developing
applications for molecules that contain carbon.1 After being introduced to this
field in my tenth standard, I have had a strong inclination towards Organic
Chemistry and particularly, esters due to their role in perfumes and flavourings
industry. Made by condensation reaction between alcohols and carboxylic acids,
esters are known for their characteristic fruity odour, causing them to have a
wide range of uses. For example, 1-methylbutyl ethanoate (from pentan-2-ol +
ethanoic acid) is claimed to be the primary flavouring agent in ‘Juicy Fruit’
chewing gum.2
Some practical applications of esters are their use in Plexiglas (a solid
transparent plastic) and Dacron (a polyester fiber) requiring large-scale
production of long chain esters.3 With the advances in technology, there are
newer, better and more cost effective ways to carry out production of esters.4
Literature Search:
During literature search, I found that esterification is one of the widely studied
reactions. I was looking for a new alternative technique to carry out the
esterification reaction.5 Some of the methods pursued by other scholarly
research groups were the use of polymer chemistry in the synthesis of esters6
and the use of microwave irradiation7.
1 “Is all around us.” Organic Chemistry. Web. 16 Dec. 2013.
http://www.acs.org/content/acs/en/careers/whatchemistsdo/careers/organic-
chemistry.htcm3
2 “Honey Bees, Whiskey and Juicy Fruit Gum.” Smells Like Science. Web. 16 Dec. 2013.
http://smellslikescience.com/honey-bees-whiskey-and-juicy-fruit-gum/
3 "Esters in Nature and Society." Esters in Nature and Society. N.p., n.d. Web. 02 Feb.
2014. <http://personal.ashland.edu/~bmohney/ket_scholars/esters.html>.
4 “ESTERIFICATION.” Esterification. Web. 20 Dec. 2013.
http://vigoschools.org/~mmc3/AP%20Chemistry/ap%20lab%20documents/Esterficat
ion.pdf
5 Manohar, Basude, Vangala R. Reddy, and Benjaram M. Reddy."Esterification by ZrO2
and Mo-ZrO2 eco-friendly solid acid catalysts." Synthetic communications 28.17 (1998):
3183-3187.
6 Theato, P. (2008), Synthesis of well-defined polymeric activated esters. J. Polym. Sci. A
Polym. Chem., 46: 6677–6687.
7 Loupy, André, et al. "The synthesis of esters under microwave irradiation using dry-
media conditions." Canadian Journal of chemistry 71.1 (1993): 90-95.

Sonication8 - an emerging technique in the frontiers of science could be extended
to esterification, though esters are traditionally made by refluxing acid and
alcohol in presence of acid catalyst. The beauty of esterification is that we can
use a wide range of combination between various carboxylic acids and alcohols
to carry out our studies. So I decided to find out whether conducting
esterification reactions using ultrasonic waves affect the equilibrium constants
of the reactions and hence affect the yield of the esters; I also wanted to
investigate the effect of sonication on esters of varying alkyl chain lengths. This
led me to the research question:
How do ultrasound waves affect the value of equilibrium constants of the
esterification reactions between ethanoic acid and five different alcohols
(methanol, ethanol, propan-2-ol, butan-1-ol, pentan-2-ol) of increasing alkyl
chain lengths?
An esterification reaction takes place when an alcohol and a carboxylic acid
condense in the presence of a catalyst (usually sulphuric acid) to yield the
corresponding ester and water. For example:
C2H5OH + CH3COOH CH3COOC2H5 + H2O
(alcohol + carboxylic acid ester + water)
The compounds in the above reaction are ethanol, ethanoic acid, ethyl ethanoate
and water respectively. The ‘ ’ symbol is used as the process of
esterification is a reversible reaction and a dynamic equilibrium is established
between the reactants and products after the reaction is allowed to rest for some
time. Dynamic equilibrium is that state of chemical equilibrium where the
forward and backward reactions occur at the same rate.9 According to Le
Chatelier’s Principle (“If a change is made to the conditions of chemical
equilibrium, then the position of equilibrium will readjust so as to minimize the
change made”)10
8 “Esters. An Introduction.” Ester. Web. 20 Dec. 2013.
http://www.chem.umass.edu/~samal/269/ester.pdf
9 John Green and Sadru Damji. IB Chemistry, Third Edition. Victoria: IBID Press, 2007.
Print. (Page 181)
Print. (Page 185)

The equilibrium constant (Kc) of a reaction can be defined as the product of the
concentration of the products divided by the product of the concentration of the
reactants.11 Its expression is:
Kc = [ester][water]
[acid][alcohol],
Since in dilute aqueous solutions, the concentration of water would not change
from its initial concentration, the expression for Kc can be simplified to:
Kc = [ester] as [water] is constant in dilute solutions
[acid][alcohol]
Higher the Kc value, more the reaction goes to forward direction and higher the
yield of ester. Since altering certain reaction conditions could shift the position of
equilibrium towards the forward direction, the yield of esters can be improved.
Hence finding the equilibrium constant and investigating the effect of carrying
out the reaction using ultrasound waves on its Kc was worthy of investigation.
Sonication is cost-effective as less use of fossil fuels was required since the
process was done under ambient temperature.
Background Research:
How do sonicators work?
An ultrasound refers to any sound that occurs beyond the frequency range of
human hearing - frequency of over 20,000 Hz. The most familiar use of an
ultrasound is to see the image of a baby in its womb. For medical purposes, the
ultrasound is sent through the required part of the body, and it bounces off
dense surfaces (the child in the womb) to give a gray image.12
An ultrasound is most commonly used as an ultrasonic cleaner used to clean
objects such as spectacles or jewelry. Ultrasonic cleaners can also be used to
clean oils off cars and weapons for federal agents. Sonication can also be used to
improve sterilization and influence the development of living cells in food.13 The
process of cleaning through ultrasound is simple; the object to be cleaned is
placed in a detergent solution of water inside the cleaning tank and sound waves
(greater than 20,000 Hz) are carried through the solution in a pattern that varies
between two phases; the high-pressure phase and the low-pressure phase. In the
Print. (Page 184)
12 “What is an Ultrasound?”. MNT. Web. 20 Dec. 2013.
http://www.medicalnewstoday.com/articles/245491.php
13 "The Uses of Ultrasound in Food Technology." The Uses of Ultrasound in Food
Technology. N.p., n.d. Web. 03 Feb. 2014.
<http://www.sciencedirect.com/science/article/pii/S135041779600034x>.

low-pressure phase, many tiny bubbles or cavities form and start sticking to the
object (cavitation). In the high-pressure phase, these bubbles implode, giving out
large amounts of energy that attacks the surface of the object, thereby cleaning
it.14 This principle is applied in chemical reactions, the electrons in the reactant
molecules get excited as the imploding cavities attack the outside of the reaction
vessel, initiating the reaction and leading to effective collisions, thus lowering the
activation energy of the reaction.
It is more environmentally friendly than other chemical cleaners and it is more
efficient as it uses less water, energy and time to clean an object.15 One major
breakthrough with ultrasound is its use in the production of bio-diesel. It was
found that bio-diesel can now be processed faster due to ultrasound-assisted
reactors.16
Plan of Action:
I had planned to investigate sonication is more effective in the production of
esters, compared to the refluxing method. To make the investigation more
general to maximum kinds of esters, I had planned to study the esterification
between ethanoic acid and five different alcohols with increasing carbon chain
lengths. The alcohols chosen are methanol (carbon-1), ethanol (carbon-2),
propan-2-ol (carbon-3), butan-1-ol (carbon-4) and pentan-2-ol (carbon-5) due to
their ready availability in the lab and because they are successive members in
the homologous series (C1-C5) of alcohols. I had chosen ethanoic acid as the
carboxylic acid due to its easy availability, low cost and wide availability in
natural fruit and flavours.17 1 mol dm-3 of sulphuric acid was used in this
reaction as a catalyst and a dehydrating agent. As a catalyst it lowers the
activation energy of the reaction for both forward and backward directions,
speeding up the reaction; however that would not increase the yield of esters. As
a dehydrating agent, it removes the water produced in the reaction, shifting the
position of equilibrium forward.
Some important details of the five alcohols used for my study are mentioned in
Table 1 below:
14 “How to use your ultrasonic cleaning system.” Tuttnauer. Web. 20 Dec. 2013.
http://www.tuttnauerusa.com/sites/default/files/assets-usa/support/Ultrasonic-CSU-
Manual.pdf
15 "Five Advantages of Ultrasonic Cleaning." Five Advantages of Ultrasonic Cleaning. N.p.,
n.d. Web. 03 Feb. 2014. <http://www.iultrasonic.com/frequently-asked-questions/five-
advantages-of-ultrasonic-cleaning.html>.
16 “Faster Biodiesel Processing with Ultrasound-Assisted Reactors”. Uidaho. N.p. n.d.
Web. 08 Feb. 2014. http://web.cals.uidaho.edu/biodiesel/files/2012/11/ultrasonic.pdf
17 "Esters in Nature and Society." Esters in Nature and Society. N.p., n.d. Web. 02 Feb.
2014. <http://personal.ashland.edu/~bmohney/ket_scholars/esters.html>.

Table 1: Structural formulae and boiling points of alcohols under study
IUPAC
Names
(A-E)
No. of
carbon
atoms
Structural formulae Boiling
Point18,19,20
Methanol:
A
1
21
64.7 C
Ethanol:
B
2
22
78.4 C
Propan-
2-ol: C
3
23
82.5 C
Butan-1-
ol: D
4
24
117.4°C
Pentan-2-
ol: E
5
25
119.3°C
18 "SmartLearner." SmartLearner. N.p., n.d. Web. 09 Feb. 2014.
<http://www.smartlearner.mobi/science/videopastpapers/organics/organics_1.htm>.
19 N.p., n.d. Web. 09 Feb. 2014. <http://avogadro.chem.iastate.edu/MSDS/Propan-2-
ol.htm>.
20 "Pentan-2-ol." 6032-29-7|pentan-2-ol|sec-amyl Alcohol. N.p., n.d. Web. 09 Feb. 2014.
<http://en.chembase.cn/substance-168826.html>.
21 "Revision Systems, Inc." Revision Systems Inc. N.p., n.d. Web. 10 Feb. 2014.
<http://revision-systems.co.uk/exam-boards/aqa/chemistry-alcohols-carboxylic-acids-
and-esters/>.
22 "." Representing Organic Structures. N.p., n.d. Web. 10 Feb. 2014.
<http://firstyear.chem.usyd.edu.au/prelab/organic_structures.shtml>.
23 "Unit 1 - Elaborations - Structural Formulas." UWEC. N.p., n.d. Web. 09 Feb. 2014.
<http://www.chem.uwec.edu/Chem150_S07/elaborations/unit1/unit1-d-structural-
formulas.html>.
24 "Creative Chemistry Molecular Models." Creative Chemistry Positional Isomers. N.p.,
n.d. Web. 10 Feb. 2014. <http://www.creative-
chemistry.org.uk/molecules/positional.htm>.

My hypothesis: The collision theory of kinetics states that a reaction takes place
when the energy of collisions exceeds the activation energy of the reaction (the
minimum amount of energy required for the reaction to occur). The sulphuric
acid molecules will collide with the water molecules produced more effectively
due to the cavitation effect of sonication, removing the water molecules (as
addition complex) more efficiently and that in turn will shift the position of
equilibrium to the right, increasing the concentration of esters formed. So the Kc
of the esterification reaction conducted in the sonicator would be higher than
that produced by refluxing the mixture of reactants. If I keep the initial
concentrations of ethanoic acid and the respective alcohols the same, formation
of more esters will lead to a higher value of Kc. As the physical properties of
esters change when the length of alkyl chain is changed ultrasound waves would
have different effect on the Kc of esterification for esters with varying alkyl chain
lengths.
25 "GCSE CHEMISTRY - What Are the Isomers of Pentanol?" GCSE Science. N.p., n.d. Web.
10 Feb. 2014. <http://www.gcsescience.com/o39.htm>.

Investigation
I have conducted esterification reactions between 1 mol dm-3 of ethanoic acid
and 1 mol dm-3 alcohols A-E (Table 1) using 1 mol dm-3 H2SO4 as catalyst under
three different reaction conditions. In Experiment 1, the alcohol-carboxylic acid
reaction mixture was heated in a water bath at 100 °C for 30 minutes; in
Experiment 3 the reaction mixture was refluxed using a heating mantle for 1
hour and in Experiment 4, the reaction mixture was sonicated using an
ultrasonic bath at 55-60 °C. The esterified reaction mixtures were allowed to
reach equilibrium and then titrated against standard NaOH solutions. From these
titre values, the unknown concentration of un-reacted acid could be found and
having known the initial concentrations of ethanoic acid and the alcohols, the
concentrations of other components at equilibrium and thus the equilibrium
constants (Kc) of each ester could be computed using the following expression
for equilibrium constant:
Kc = [ester]
[acid][alcohol]
Temperature was kept constant as Kc is a constant at a particular temperature
only. Therefore the five esters that were going to be produced were: methyl
ethanoate (from methanol), ethyl ethanoate (from ethanol), 1-methylethyl
ethanoate (from propan-2-ol), butyl ethanoate (from butan-1-ol) and 1-
methylbutyl ethanoate (from pentan-2-ol) respectively.
In Experiment 2, I computed the correction values for 1 mol dm-3 of H2SO4
catalyst. NaOH will react with the un-reacted acetic acid in the reaction mixture
and H2SO4 catalyst will also neutralize NaOH, so we had to eliminate that volume
from our titre values. Titrations of alcohol-carboxylic acid reaction mixtures
were performed before and after adding requisite volume of H2SO4. The
difference in the titre values were recorded.
The five esterification reactions are: (Alcohol used)
1. CH3OH (aq) + CH3COOH (aq) CH3COOCH3 (aq) + H2O (l) (Methanol)
2. C2H5OH (aq) + CH3COOH (aq) CH3COOC2H5 (aq) + H2O (l) (Ethanol)
3. C3H7OH (aq) + CH3COOH (aq) CH3COOC3H7 (aq) + H2O (l) (Propan-2-
ol)
4. C4H9OH (aq) + CH3COOH (aq) CH3COOC4H9 (aq) + H2O (l) (Butan-1-
ol)
5. C5H11OH (aq) + CH3COOH (aq) CH3COOC5H11 (aq) + H2O (l) (Pentan-
2-ol)

1
The variables for experiments 1, 3 and 4 are:
Independent variable: Using five different alcohols with increasing carbon chain
lengths (C1-C5).
Dependent variable: The equilibrium constant (Kc) of the reaction at the
particular temperature.
Controlled variables: Variables such as concentration and volume of the
reactants and catalyst were maintained at all times. Duration of the reaction and
temperature of the reaction were also maintained throughout.
Experiment 1:
Aim: To determine the equilibrium constant of the esterification reaction
between ethanoic acid and the alcohols A-E using 1 mol dm-3
sulphuric acid as
catalyst by heating the reaction mixtures in water bath at 90-100 °C.
For experiments 1, 3 and 4:
1. I had prepared 1 mol dm-3
of the following compounds using the dilution
method. The volume of each compound in 1 mol dm-3
of solution is:
12.01 cm3 of ethanoic acid in 200 cm3 distilled water
6.4 cm3 of methanol in 200 cm3 distilled water
9.2 cm3 of ethanol in 200 cm3 distilled water
12.0 cm3 of propan-2-ol in 200 cm3 distilled water
14.8 cm3 of butan-1-ol in 200 cm3 distilled water
17.6 cm3 of in 200 cm3 – Pentan-2-ol
1.0 cm3 in 20 cm3 – Sulphuric acid
2. After pouring 200 cm3 of ethanoic acid solution, 200 cm3 of the respective
alcohol solution and 20 cm3 of 1 mol dm-3
sulphuric acid into a 500 cm3
beaker, I stirred the solution till it became homogenous.
Methodology:
I placed the respective solutions into the water bath at a temperature of
90-100°C for half an hour.
I removed the respective solution from the water bath, covered the top of
the beaker with foil and let the reaction mixture rest for one week.
After one week, I took 3 titrations of 10 cm3 of each solution using 1 mol
dm-3
NaOH solution and phenolphthalein as an indicator.
It was observed that butan-1-ol and pentan-2-ol form a separate layer over the
water, which shows that as you go up in the homologous series of alcohols,
solubility decreases. It was also interesting to note some of the smells of the

esters. 1-Methylbutyl ethanoate gave off smell of bananas and ethyl ethanoate
gave off a smell of nail polish remover.
Data Collection:
Temperature of the lab: 23 °C.
Titre values – Water bath
Table 2: Methyl ethanoate – Methanol + ethanoic acid
Initial volume -
cm3 ( 0.05)
Final volume - cm3
( 0.05)
Difference in
volume - cm3
( 0.10)
1. 0.00 5.80 5.80
2. 5.80 11.40 5.60
3. 11.40 17.00 5.60
Table 3: Ethyl ethanoate – Ethanol + ethanoic acid
Initial volume -
cm3 ( 0.05)
Final volume - cm3
( 0.05)
Difference in
volume - cm3
( 0.10)
1. 0.00 5.50 5.50
2. 5.50 11.40 5.90
3. 11.40 17.30 5.90
Table 4: 1-Methylethyl ethanoate – Propan-2-ol + ethanoic acid
Initial volume -
cm3 ( 0.05)
Final volume - cm3
( 0.05)
Difference in
volume - cm3
( 0.10)
1. 0.00 5.40 5.40
2. 5.40 11.00 5.60
3. 11.00 16.60 5.60
Table 5: Butyl ethanoate – Butan-1-ol + ethanoic acid
Table 6: 1-Methylbutyl ethanoate – Pentan-2-ol + ethanoic acid
Initial volume -
cm3 ( 0.05)
Final volume - cm3
( 0.05)
Difference in
volume - cm3
( 0.10)
1. 0.00 2.80 2.80
2. 2.80 6.00 3.20
3. 6.00 9.20 3.20
Initial volume -
cm3 ( 0.05)
Final volume - cm3
( 0.05)
Difference in
volume - cm3
( 0.10)
1. 0.00 2.60 2.60
2. 2.60 6.00 3.40
3. 6.00 9.40 3.40

3
Table 7: Summary of the titre values of esters formed by water bath method
Name of Ester (Alcohols A-E) Volume of 1 mol dm-3 NaOH required
for neutrlisation of reaction mixtures -
cm3 ( 0.05)
Methyl ethanoate (A) 5.60
Ethyl ethanoate (B) 5.90
1-Methylethyl ethanoate (C) 5.60
Butyl ethanoate (D) 3.40
1-Methylbutyl ethanoate (E) 3.20
Data Processing:
Before calculating equilibrium constant (Kc), a series of steps must be followed26:
1. The number of moles of base must be found.
As we know, c = n/v (Concentration = Number of moles/ volume) so
n = c x v. Concentration is in (mol dm-3
) and volume (Titre value) will be
in dm-3
so it has to be converted from cm3 to dm-3
. This can be done so by
dividing the value by 1,000.
2. The number of moles of acid must be found.
This can be done so by multiplying the number of moles of base with the
ratio of the co-efficients of the acid and the base (Always 1:1 in this case).
3. The concentration of acid can now be found.
As mentioned in step 1, c = n/v.
Therefore the concentration of acid = number of moles/volume of acid
used (In dm-3
again).
From here the equilibrium constant can be found.
If the value of step 3 is (1-x) mol dm-3, then the concentration of un-
reacted acid = x mol dm-3. The concentration of un-reacted alcohol will
also be the same, and the concentration of the ester formed shall be = (1
– x) mol dm-3. 27
So the formula for Kc that we can use is:
26 “Titration of Hydrochloric Acid with Sodium Hydroxide”. Austin Peay State University
Department of Chemistry. Web. 23 Dec. 2013.
https://www.apsu.edu/sites/apsu.edu/files/chemistry/SP12_1011_Titration_of_Hydro
chloric_Acid_with_Sodium_Hydroxide_0.pdf
27 Please see appendix 2 for detailed calculations.

Kc = (1-x) mol dm-3
(x)2 mol dm-3
To simplify the formula above, our units for Kc will always be in dm3/mol in this
case. x is to the power of 2 because the concentration of acid and alcohol at
equilibrium will be the same. To further simplify the steps above, x = Titre
value/10.
So the following values of Kc for the esters were:
Table 8: Equilibrium constant values of esters formed by water bath method
Name of ester
(Alcohols A-E)
Titre value/10 =
(x) cm3
Kc= (1-x)/(x)2 Kc value
(dm3/mol)
Methyl ethanoate
(A)
5.60/10 = 0.56 (1-0.56)/(0.56)2 1.40
Ethyl ethanoate
(B)
5.90/10 = 0.59 (1-0.59)/(0.59)2 1.17
1-Methylethyl
ethanoate (C)
5.60/10 = 0.56 (1-0.56)/(0.56)2 1.40
Butyl ethanoate
(D)
3.40/10 = 0.34 (1-0.34)/(0.34)2 5.71
1-Methylbutyl
ethanoate (E)
3.20/10 = 0.32 (1-0.32)/(0.32)2 6.64
Results and Discussion:
As we can see, the Kc values for esters made from alcohols D and E are
significantly higher than those made from alcohols A-C. This is because the lower
alcohols with lesser number of carbon atoms (A-C) have low boiling points and
were more volatile, and hence I had realized from the high titre values and the
low Kc values that esterification reaction did not take place at all for lower
alcohols as at that temperature (90-100 °C), the alcohols (boiling points of 64.7,
78.4 and 82.5 °C for A-C respectively) evaporated from the reaction mixture
leaving more acid content. I had also realized that 1 mol dm-3 sulphuric acid in
the mixture was not accounted for during titration. This must not be included in
the titre values as it was not a reactant in the reaction but simply a catalyst.
Therefore I set out to make corrections and exclude the volume of NaOH used to
neutralise 1 cm3 sulphuric acid from the recorded titre values.

5
Experiment 2:
Aim: To determine the volume of 1 mol dm-3 sodium hydroxide solution
required to neutralize 1 cm3 of 1 mol dm-3 sulphuric acid catalyst that needs to
be accounted for while calculating the titre values and to make corrections in the
titre values for 1 mol dm-3 sulphuric acid.
Methodology:
After mixing 200 cm3 of ethanoic acid solution with 200 cm3 of alcohol
solution in a 500 cm3 beaker, I stirred the solution till it became homogenous.
I titrated 10 cm3 of the solution with 1 mol dm-3 of NaOH using
phenolphthalein as an indicator.
After noting down those titre values, I added the 20 cm3 of 1 mol dm-3 of
sulphuric acid to the solution, stirred well to make the solution homogeneous
and then carried out three titrations again.
The difference is the volume of 1 mol dm-3 sodium hydroxide solution
required to neutralize 1 mol dm-3 sulphuric acid catalyst which had to be
subtracted from the titrations of the esterification reactions.
Data Collection:
Temperature of the lab: 20.5 °C
Titre values before sulphuric acid was added
Initial volume -
cm3 ( 0.05)
Final volume -
cm3 ( 0.05)
Difference in volume
- cm3 ( 0.10)
1. 0.00 4.80 4.80
2. 4.80 9.60 4.80
3. 9.60 14.30 4.70
Initial volume -
cm3 ( 0.05)
Final volume -
cm3 ( 0.05)
- cm3 ( 0.10)
1. 0.00 5.50 5.50
2. 5.50 11.30 5.80
3. 11.30 17.10 5.80

Initial volume -
cm3 ( 0.05)
Final volume -
cm3 ( 0.05)
- cm3 ( 0.10)
1. 0.00 6.30 6.30
2. 6.30 12.60 6.30
3. 12.60 19.00 6.40
Initial volume -
cm3 ( 0.05)
Final volume -
cm3 ( 0.05)
- cm3 ( 0.10)
1. 0.00 5.40 5.40
2. 5.40 10.90 5.50
3. 10.90 16.40 5.50
Initial volume -
cm3 ( 0.05)
Final volume -
cm3 ( 0.05)
- cm3 ( 0.10)
1. 0.00 5.50 5.50
2. 5.50 11.00 5.50
3. 11.00 16.60 5.60
Table 14: Summary of the titre values of alcohol-acid mixtures before adding
1 mol dm-3 sulphuric acid
Name of alcohol + acid (Alcohols A-E) Volume of 1 mol dm-3 NaOH required
for neutralisation of reaction mixtures
before adding acid catalyst - cm3
( 0.05)
Titre values after 1 mol dm-3 sulphuric acid was added
Initial volume -
cm3 ( 0.05)
Final volume -
cm3 ( 0.05)
- cm3 ( 0.10)
1. 0.00 5.40 5.40
2. 5.40 11.10 5.70
3. 11.10 16.50 5.40

7
Initial volume -
cm3 ( 0.05)
Final volume -
cm3 ( 0.05)
- cm3 ( 0.10)
1. 0.00 5.90 5.90
2. 5.90 11.90 6.00
3. 11.90 17.90 6.00
Initial volume -
cm3 ( 0.05)
Final volume -
cm3 ( 0.05)
- cm3 ( 0.10)
1. 0.00 6.60 6.60
2. 6.60 13.20 6.60
3. 13.20 19.70 6.50
Initial volume -
cm3 ( 0.05)
Final volume -
cm3 ( 0.05)
- cm3 ( 0.10)
1. 0.00 5.80 5.80
2. 5.80 11.60 5.80
3. 11.60 17.10 5.50
Initial volume -
cm3 ( 0.05)
Final volume -
cm3 ( 0.05)
- cm3 ( 0.10)
1. 0.00 6.10 6.10
2. 6.10 12.20 6.10
3. 12.20 18.20 6.00
Table 20: Summary of the titre values of alcohol-acid mixtures after adding 1
mol dm-3 sulphuric acid
for neutrlisation of reaction mixtures
- cm3 ( 0.05)

Data Processing:
Table 21: Difference between both sets of titre values of alcohol-acid
mixtures
Name of Ester
(Alcohols A-E)
Value 1
(before adding
catalyst) - cm3
( 0.05)
Value 2 (after
adding catalyst) -
cm3 ( 0.05)
Value 3
(Difference) - cm3
( 0.10)
Methyl ethanoate (A) 4.80 5.40 5.40 – 4.80= 0.60
Ethyl ethanoate (B) 5.80 6.00 6.00 – 5.80 = 0.20
1-Methylethyl
ethanoate (C)
6.30 6.60 6.60 – 6.30 = 0.30
Butyl ethanoate (D) 5.50 5.80 5.80 – 5.50 = 0.30
1-Methylbutyl
ethanoate (E)
5.50 6.10 6.10 – 5.50 = 0.60
The values found in Table 6 (value 3) for each alcohol-acid mixture tell us that
the next time we take titre values of esters, the amounts given above must be
subtracted from the titre value in order to give us a more accurate equilibrium
constant value. However, the problem with the alcohols evaporating and not
being present in the final reaction mixture still had to be dealt with. This is what
led me to experiment 3.
Experiment 3:
between ethanoic acid and the alcohols A-E using 1 mol dm-3 sulphuric acid as a
catalyst by refluxing the reaction mixtures for one hour.
In order to avoid the evaporation of low boiling alcohols and to ensure a
complete esterification reaction, I needed to use a new, more efficient method,
refluxing the reaction mixtures using heating mantle and a Soxhlet apparatus.
The main role of reflux is to react compounds through constant vaporisation and
condensation. As this is taking place the reactants are reacting to produce the
ester. The main advantage of using a reflux setup over a water bath setup is that
the temperature does not go beyond the boiling point of the mixture. It simply
gets vaporised and then condenses back down to the flask. Therefore this would
give me a more reliable value of equilibrium constant, which could be compared
with that of sonication later. I had not allowed the refluxed solutions to stand for
a week but only allowed them to come to room temperature before titration as it
was assumed that the solutions produced by using reflux for one hour had
already reached equilibrium.

9
Methodology:
I transferred the prepared
alcohol-acid reaction
mixture to a round
bottom flask that was
attached to the Soxhlet
apparatus using grease
and cardboard pieces (for
secured clamping) (as
shown in the photo
below).
Figure 1: Reflux setup for Esterification
It can be seen that the heating mantle at the bottom is connected to the
plug point has been set to a temperature of 80 C. The condenser Soxhlet
apparatus on the top has an inlet that is connected to the spout of the tap
and an outlet that leads to the sink. The round bottom flask that contains
the reaction mixture is at the bottom of the setup and placed on the
heating mantle. A few boiling chips consisting of pieces of broken
porcelain have been added to the round bottom flask to prevent any
damage that could be done to the apparatus and to keep the boiling
solution from bumping.28
After refluxing all the solutions for one hour, I removed the solution from
the setup, allowed to come down to the room temperature and took 3
titrations of 10 cm3 of each solution using 1 mol dm-3 NaOH and
phenolphthalein as an indicator.
Data Collection:
Temperature of the lab: 16 °C
Titre values – Reflux
Initial volume -
cm3 ( 0.05)
Final volume - cm3
( 0.05)
Difference in
volume - cm3
( 0.10)
1. 0.00 6.90 6.90
2. 6.90 16.90 10.00
3. 16.90 23.80 6.90
28 “Refluxing.” The Organic Chemistry Undergraduate Laboratories. Web. 23 Dec. 2013.
http://www.chem.wisc.edu/areas/organic/orglab/tech/reflux.htm

Initial volume -
cm3 ( 0.05)
Final volume - cm3
( 0.05)
Difference in
volume - cm3
( 0.10)
1. 0.00 5.70 5.70
2. 5.70 11.30 5.60
3. 11.30 17.00 5.70
Initial volume -
cm3 ( 0.05)
Final volume - cm3
( 0.05)
Difference in
volume - cm3
( 0.10)
1. 0.00 7.10 7.10
2. 7.10 14.20 7.10
3. 14.20 21.50 7.30
Initial volume -
cm3 ( 0.05)
Final volume - cm3
( 0.05)
Difference in
volume - cm3
( 0.10)
1. 0.00 6.50 6.50
2. 6.50 12.90 6.40
3. 12.90 19.40 6.50
Initial volume -
cm3 ( 0.05)
Final volume - cm3
( 0.05)
Difference in
volume - cm3
( 0.10)
1. 0.00 7.30 7.30
2. 7.30 14.60 7.30
3. 14.60 21.80 7.20
Table 27: Summary of the titre values of esters formed by reflux method
for neutralization of reaction mixtures -
cm3 ( 0.05)

1
Table 28: Volume of NaOH solution required to neutralize reaction mixtures
after correction for sulphuric acid catalyst
Name of Ester
(Alcohols A-E)
Old titre value
- cm3 ( 0.05)
Volume to
subtract (from
table 6) - cm3
( 0.05)
Difference =
volume of 1 mol
dm-3 NaOH
required to
neutralize
esterified reaction
mixtures - cm3
( 0.10)
Methyl ethanoate
(A)
6.90 0.60 6.90 – 0.60 = 6.30
Ethyl ethanoate (B) 5.70 0.20 5.70 – 0.2 = 5.50
1-Methylethyl
ethanoate (C)
7.10 0.30 7.10 – 0.3= 6.80
Butyl ethanoate (D) 6.50 0.30 6.50 – 0.30 = 6.20
1-Methylbutyl
ethanoate (E)
7.30 0.60 7.30 – 0.60 = 6.70
Data Processing:
Table 29: Equilibrium constant values of esters formed by reflux method
Name of Ester
(Alcohols A-E)
Titre value/10 =
(x) - cm3
Kc = (1-x)/(x)2 Kc value
(dm3/mol)
Methyl ethanoate
(A)
6.30/10 = 0.63 (1-0.63)/(0.63)2 0.93
Ethyl ethanoate
(B)
5.50/10 = 0.55 (1-0.55)/(0.55)2 1.49
1-Methylethyl
ethanoate (C)
6.80/10 = 0.68 (1-0.68)/(0.68)2 0.69
Butyl ethanoate
(D)
6.20/10 = 0.62 (1-0.62)/(0.62)2 0.98
1-Methylbutyl
ethanoate (E)
6.70/10 = 0.67 (1-0.67)/(0.67)2 0.73
As we can see from the Kc values given above in Table 9 and the titre values in
Table 7, although the titre values were considerably high, the Kc values provide
for a better analysis as there is consistency of values this time. With the water
bath, there were two extremes of Kc values found. The only issue that might have
been faced was that since the reflux produced solutions were not given time to
rest, it is questioned whether the equilibrium constant might have been higher
had they been given one week or even 24 hours to rest. This could have been
verified by taking a set of titrations one week after the reflux reaction was
carried out.

Experiment 4:
between ethanoic acid and the alcohols A-E using 1 mol dm-3 sulphuric acid as
catalyst by using a sonicator bath.
Methodology:
I transferred the prepared alcohol-acid reaction mixture to a 250 cm3
conical flask that was partially immersed into the 40 kHz sonicator bath
through a clamp stand (as shown in the photo below). A cardboard piece
was also used to ensure that the flask did not fall into the bath. The
following set up was used:
Figure 2: Ultrasound setup for esterification – outside
Figure 3: Ultrasound setup for esterification – inside

3
I placed the respective solution into the sonicator bath filled with water
set at 55-60 C and allowed the reaction to take place using ultrasound
waves of frequency of over 20,000 Hz for half an hour.
The sonicator used was the LMUC-2A Ultrasonic cleaner made by Lab
Man Scientific Instruments PVT. LTD.
Its ultrasonic frequency was 40 kHz or 40,000 Hz.
It was observed during the reaction as seen in figure 3 that small bubbles
(cavities) were forming and coming closer to the flask.
After half an hour, I removed the respective solution from the sonicator
bath, covered the top of the beaker with foil and let the esterified reaction
mixture rest for one week.
After one week, I took 3 titrations of 10 cm3 of each solution using 1 mol
dm-3 NaOH and phenolphthalein as an indicator.
Data Collection:
Temperature of the lab: 22 °C
Titre values – Ultrasound
Initial volume -
cm3 ( 0.05)
Final volume -
cm3 ( 0.05)
- cm3 ( 0.10)
1. 0.00 5.10 5.10
2. 5.10 10.30 5.20
3. 10.30 15.50 5.20
Initial volume -
cm3 ( 0.05)
Final volume -
cm3 ( 0.05)
- cm3 ( 0.10)
1. 0.00 5.10 5.10
2. 5.10 10.20 5.10
3. 10.20 15.40 5.20
Initial volume -
cm3 ( 0.05)
Final volume -
cm3 ( 0.05)
- cm3 ( 0.10)
1. 0.00 5.00 5.00
2. 5.00 10.00 5.00
3. 10.00 15.20 5.20

Initial volume -
cm3 ( 0.05)
Final volume -
cm3 ( 0.05)
- cm3 ( 0.10)
1. 0.00 5.30 5.30
2. 5.30 10.50 5.20
3. 10.50 15.70 5.20
Initial volume -
cm3 ( 0.05)
Final volume -
cm3 ( 0.05)
- cm3 ( 0.10)
1. 0.00 4.10 4.10
2. 4.10 8.30 4.20
3. 8.30 12.50 4.20
Table 35: Summary of the titre values of esters formed by ultrasound method
Name of Ester (Alcohols A-E) Volume of 1 mol dm-3 NaOH
required for neutralization of
reaction mixtures - cm3 ( 0.05)
Table 36: Volume of NaOH solution required to neutralize reaction mixtures
after correction for sulphuric acid catalyst
Name of Ester
(Alcohols A-E)
Old titre value
- cm3 ( 0.05)
Volume to
subtract (from
table 6) - cm3
( 0.05)
Difference =
volume of 1 mol
dm-3 NaOH
required to
neutralize
esterified reaction
mixtures - cm3
( 0.10)
Methyl ethanoate
(A)
5.20 0.60 5.20 – 0.60 = 4.60
Ethyl ethanoate
(B)
5.10 0.20 5.10 – 0.20 = 4.90
1-Methylethyl
ethanoate (C)
5.00 0.30 5.00 – 0.30 = 4.70
Butyl ethanoate
(D)
5.20 0.30 5.20 – 0.30 = 4.90
1-Methylbutyl
ethanoate (E)
4.20 0.60 4.20 – 0.60 = 3.60

5
Data Processing:
Table 37: Equilibrium constant values of esters formed by ultrasound
method
Name of Ester
(Alcohols A-E)
Titre value/10 =
(x) - cm3
Kc = (1-x)/(x)2 Kc value
(dm3/mol)
Methyl
ethanoate (A)
4.60/10 = 0.46 (1-0.46)/(0.46)2 2.55
Ethyl ethanoate
(B)
4.90/10 = 0.49 (1-0.49)/(0.49)2 2.12
1-Methylethyl
ethanoate (C)
4.70/10 = 0.47 (1-0.47)/(0.47)2 2.40
Butyl ethanoate
(D)
4.90/10 = 0.49 (1-0.49)/(0.49)2 2.12
1-Methylbutyl
ethanoate (E)
3.60/10 = 0.36 (1-0.36)/(0.36)2 4.94
As we can see from the Kc values given above in Table 37 and the titre values
given in Table 36, the ultrasound method has given a greater yield of esters in
terms of concentration. The only issue during this reaction might have been that
the speed of the reaction. Since the temperature was low and the flask was not
completely immersed into the bath, the reaction might not have reached
completion after half an hour. However, the reaction mixture was allowed to
reach equilibrium for one week.
Conclusion
Table 38: Comparison of the two sets of Kc values (Reflux and Ultrasound)
Name of Ester (Alcohols A-
E)
Kc value - Reflux
(dm3/mol)
Kc value - Ultrasound
(dm3/mol)
Methyl ethanoate (A) 0.93 2.55
Ethyl ethanoate (B) 1.49 2.12
1-Methylethyl ethanoate
(C)
0.69 2.40
Butyl ethanoate (D) 0.98 2.12
1-Methylbutyl ethanoate
(E)
0.73 4.94
The table above shows different Kc for esterification reactions by refluxing and
sonication. The titre values suggest that esterification has taken place. The titre
values of refluxing method are higher which seems to suggest that the reaction
has not reached completion and the low Kc of their respective esters agree with
it. Since the titre values are high, the unreacted acid content will probably be

high, hence the yield of esters will be less. According to my hypothesis, the Kc of
the esters produced by sonicator should be higher and this proved correct as the
Kc values of sonicator were higher than those produced by refluxing. This proves
that the sonicator is a more effective approach to esterification as it improves the
yield of esters.
Can any pattern be detected from the Kc values of esters of varying alkyl
chain lengths (A-E)?
Figure 4: Comparison of Kc values of all 3 reactions
Looking at figure 4, it can be inferred that varying alkyl chain lengths do not
cause Kc values to increase or decrease in a gradual manner. The Kc remains
unaffected for the lower alcohols A-C and remains the same under any reaction
condition. However, for high boiling and less soluble higher alcohols D and E,
sonication even at ambient temperature, resulted in greater yield of esters, also
high temperature in water bath has allowed these reaction mixtures to go
further towards formation of esters as compared to refluxing. In case of
ultrasound and water bath, 1-methylbutyl ethanoate was produced in higher
yields whereas in case of refluxing, ethyl ethanoate gave the maximum yield.
Although the Kc for the first 3 esterifications using water bath are low, the last
two are even higher than those of the ultrasound-assisted esterification. This
could be because the temperature of the water bath was high at 90-100°C so this
caused the forward reaction to occur faster when the alcohols did not evaporate
(butan-1-ol, pentan-2-ol) and so their Kc values came out higher.
0
1
2
3
4
5
6
7
A (C1) B (C2) C (C3) D (C4) E (C5)
Kcvalues
Esters of varying alkyl chain lengths
Comparison of Kc values of all 3
reactions
Water Bath
Reflux
Ultrasound

7
Evaluation
How reliable was my data?
In case of water bath, the volume of 1 mol dm-3 NaOH required to
neutralize the sulphuric acid in the solution was not subtracted from the
values before calculating Kc.
In case of reflux, the solutions were not allowed to rest for a week before
calculating Kc.
In case of ultrasound, a high temperature was not used for the reaction, a
medium temperature of 55-60°C was used.
Since the temperature of the lab varied during the time of the reactions,
this might have caused the Kc values to change according to temperature.
For instance, the Kc values of esters produced by reflux could be lower
than expected since the temperature of the lab recorded at that time was
the lowest of the 4 experiments.
Therefore comparing the three sets of Kc values without controlling all the
variables impacted my conclusion.
How reliable are the secondary sources?
While looking for ways to calculate Kc, I got misled by an article in Austin Peay
State University’s “Titration of Hydrochloric Acid with Sodium Hydroxide”.29 In
page 3 of the document what it refers as ‘initial concentration of acid’, I actually
found this value to be ‘concentration of acid reacted’. Sometimes web resources
confuse us and do not provide authentic information.
Future Scope:
I had set out to determine how effective the use of ultrasound was in the
formation of esters. From the equilibrium constant values measured, it is clear
that the use of ultrasound gives better yield of esters as compared to the
traditional refluxing. The use of ultrasound in esterification is cost effective and
could positively impact companies and their costs of production all around the
world. Besides esterification, sonication can be extended to so many industrially
important chemical reactions to not only enhance speed but also produce greater
yields of products, at the same time using lesser toxic materials and lesser fuel
usage.
29 “Titration of Hydrochloric Acid with Sodium Hydroxide”. Austin Peay State University
Department of Chemistry. Web. 23 Dec. 2013.
https://www.apsu.edu/sites/apsu.edu/files/chemistry/SP12_1011_Titration_of_Hydro
chloric_Acid_with_Sodium_Hydroxide_0.pdf

Appendices:
Appendix 1:
Materials and Apparatus used:
500 cm3 Beaker
200 cm3 Beaker
150 cm3 Conical flask
250 cm3 Round bottom flask
Dropper
1000 cm3 Measuring cylinder
Pipette
Pipette Pump
Burette
Clamp stand
Boiling chip
Cardboard pieces
Stirrer
Latex Gloves
Water Bath
Sonicator Bath
Reflux apparatus
Foil
Chemicals used:
ethanoic acid
Methanol
Ethanol
Propan-2-ol
Butan-1-ol
Pentan-2-ol
1 mol dm-3 Sulphuric acid
Distilled water
Phenolphthalein
Sodium Hydroxide
Grease

9
Appendix 2:
Detailed calculations for finding Kc:
When produced by reflux:
1. Methyl ethanoate –
Moles of NaOH = 1 mol dm-3 x 6.3/1000 dm3= 0.0063 mol of NaOH.
Moles of CH3COOH = 0.0063 mol x 1/1 = 0.0063 mol of CH3COOH.
Conc. of CH3COOH = 0.0063 mol/(10/1000) dm3= 0.63 mol dm-3 of
CH3COOH.
Therefore the Kc = (1 - 0.63)/0.632 = 0.93 dm3/mol.
2. Ethyl ethanoate –
Moles of NaOH = 1mol dm-3 x 5.5/1000 dm3= 0.0055 mol of NaOH.
CH3COOH.
3. 1-Methylethyl ethanoate –
CH3COOH.
4. Butyl ethanoate –
CH3COOH.
5. 1-Methylbutyl ethanoate –

CH3COOH.
When produced by sonicator:
1. Methyl ethanoate –
CH3COOH.
2. Ethyl ethanoate –
CH3COOH.
3. 1-Methylethyl ethanoate –
CH3COOH.
4. Butyl ethanoate –
CH3COOH.

1
5. 1-Methylbutyl ethanoate –
CH3COOH.

Bibliography
Books
1. John Green and Sadru Damji. IB Chemistry, Third Edition. Victoria: IBID
Press, 2007. Print.
Web
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3
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23. Manohar, Basude, Vangala R. Reddy, and Benjaram M.
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5
Acknowledgements
I would like to acknowledge the assistance and support of the following people:
Dr. Sriparna Chakrabarti, Supervisor and Chemistry Teacher
Mr. Vijay Sharma, Laboratory Technician
Ms. Manisha Malhotra, Principal
Ms. Anjali Sharma, Extended Essay and IB Co-ordinator
Ms. Anuradha Goyal, Mother
Mr. Vinay Goyal, Father
Mr. Arpit Goyal, Brother

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