Hydrolysis of esters in basic solution

Zeinab Ahmed Elbhnsawi

193247

Submitted to: Dr. Ziad Khalifa

Physical Chemistry

Year 2, Chemical Engineering

The British University in Egypt

Paper format: APA style with BUE guidelines

Abstract

The following lab report discusses the hydrolysis of ester in alkaline medium where the aim

is to find the rate constant and the half lifetime of the reaction where a certain procedure was

followed by preparing certain concertation of each used substance then adding them so that the

reaction occurs across a certain timeline where titration should be done several times to know x

values then a graph is plotted between x/a-x and time so that K is calculated from its slope and

t1/2 is calculate by using t1/2= 1/K * Va so that k was found to be 6.08*10 -4 and t1/2 was 197.3

minutes.

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Table of contents

Abstract..........................................................................................................................................2

Table of contents............................................................................................................................3

Introduction....................................................................................................................................4

Experimental method....................................................................................................................9

Experimental results....................................................................................................................10

Conclusion....................................................................................................................................12

Sources of errors..........................................................................................................................13

References.....................................................................................................................................14

Table of figures

Figure 1. Alkali hydrolysis of esters................................................................................................5

Figure 2. acidic hydrolysis of esters................................................................................................5

Figure 3. rate determining step........................................................................................................6

Figure 4. increasing concentrations.................................................................................................7

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Introduction

Esters can perform many reactions. One of the most important reactions is hydrolysis,

which is its reaction with water generally, it can occur in basic or acidic medium where it is

considered as the most important reaction of esters. In basic medium, an ester is hydrolyzed by

an alkali to produce an alcohol and a carboxylate salt where ester should be heated in the use of a

reflux then a base like sodium hydroxide is added where this reaction is irreversible and gives

better results than that of acidic medium where it produces salt then can be converted to an

alcohol by adding an excess amount of any strong acid where this reaction is called

saponification as it is preparation of soap (Hydrolysis of Esters, 2021).

Figure 1. Alkali hydrolysis of esters

In acidic hydrolysis, the reverse of esterification occur where dilute acid is used to hydrolyze the

ester into an alcohol and a carboxylic acid but this reaction is reversible and never gets complete

so that it is less used than alkali hydrolysis (Clark, 2016).

Figure 2. acidic hydrolysis of esters

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Activation energy has many definitions according to its field, in chemical field, activation energy

can be defined as the least value of energy needed to cause the chemical reaction to start or the

chemical bonds to be broken where it is calculated by a certain equation in which E a is the

activation energy (Britannica, 2021),

−Ea
RT
k=A.e

Where k refers to the rate constant of the reaction where rate determining steps are applied which

is the slowest step used to determine the rate of a reaction of two consecutive parts. Where if the

reaction passes by more than one step, one of these steps is the slowest one so that the whole

reaction rate depends on this step so it is known as the rate determining step and its value can be

calculated using a certain relation (learning, n.d.).

Figure 3. rate determining step

The rate of a chemical reaction can be affected by many factors. Reactants chemical nature,

reactants’ subdivision state, presence of catalyst, temperature and concentrations of reactants are

these factors where each of them has its own specifications. When it comes to the reactants’

nature, it differs from one substance to another where some elements react rapidly while others

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react slowly, so that the rate differs according to the characteristics of each reactant. The

reactants’ subdivision refers to the contact between the two phases of the reaction where a liquid

reacts with a solid faster than two solids reaction. The presence of catalyst affects the rate of

reaction where it lowers the activation energy so that the reaction goes faster. High temperatures

make reactions goes faster while low ones make it goes slower which can appear in the spoiling

of food in the fridge and out of it where it gets spoiled faster outside the fridge. Concentration of

the reaction is from the major factors affecting the rate of the reaction. When the concentration

of the reactants increases, the rate of the reaction increases where the increase of concentrations

increases the number of collisions at the same time so that reaction proceeds faster (Theopold,

2020).

Figure 4. increasing concentrations

The rate of the reaction is measured using equation called the rate equation where for the

following reaction,

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the rate can be calculated using the following equation,

in which k is the rate constant, x is the order of the first reactant, y is the order of the second, A

and B are concentrations of the reactants respectively. Where x and y define the order of reaction

which defines the effect of this substance of the rate of the reaction so that if it was zero then it

doesn’t affect the reaction rate while if it was1 or 2 then it affects it. The order of the reaction is

the sum of x and y and their values can be known by using graphs to see the relation between

concentration and time and know the order (clark, 2013).

The molecularity of reaction is known as the number of molecules that participate in the rate

determining step, so when it is single molecule, it is unimolecular, two molecules are

bimolecular and three are termolecular (Reusch, 2020).

The second order reaction is reaction where two reactants are first order or one of its reactants ir

from second order so it can be represented by the following two reactions (second order

reactions, n.d.),

r =k [ A ][ B ]

2
r =[ A ]

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Experimental method

1. 100 ml of 0.1 N of each of Na2CO3, HCL and NaOH are prepared.

2. Original A is 12 ml.

3. Dilute 100 ml of N/40 HCL, N/20 and N/40 NaOH.

4. 100 ml of N/20 ethyl acetate is prepared.

5. Using pipette, 50 ml of the N/20 ethyl acetate and NaOH is transferred to two separate

dry flasks and keep at 20ο C.

6. Add base to ester quickly, mix and record timing.

7. Remove 10 ml of the mixture which is reacting, record time and run to a flask with 100

ml water distilled and 10 ml N/40 HCL then titrate the excess in presence of

phenolphthalein.

8. Last step is repeated till 80 mins to fill the table by doing multiple titrations.

For calculations:

1. Tabulate results of x, A-x and x/a-x in the table.

2. Plot graph between time and x/a-x.

3. Get the slope which equals AK then divided by original concentration to get K which

is the rate constant.

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Experimental results

A = 12 ml

Time (min) X (ml) A-x (ml) x/a-x

2 3.6 8.4 0.42857

5 5.3 6.7 0.791

10 6.8 5.2 1.3

15 7.8 4.2 1.857

20 8.6 3.4 2.5294

30 9 3 3

40 10.1 1.9 5.315789

60 10.4 1.6 6.5

80 10 2 5

by plotting graph between x/a-x on y-axis and time on x-axis,

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The slope was found to be equal 0.073 so that K is calculated from the following relation,

slope= A° K

By knowing that Ao is 12 ml so that K will be equal 0.0073/12, K = 6.083x10-4.

Then using the following relation t1/2 is calculated,

1 1
t 1= = VA
2 K [ Ao] K

so that t1/2 will be equal 197.3 minutes.

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Conclusion

The main aim of the experiment was to find rate constant and half lifetime of the experiment

where ethyl acetate is getting saponified in basic medium. This was done by preparing certain

concentration of NaOH, Na2CO3, HCl and ethyl acetate the make a certain reaction in order to be

used in a certain timeline by repeated titration so that the values of x gets tabulated till time

reaches 80 minutes then these tabulated value of x and time are used to find difference between x

and initial volume then a graph is plotted between x/a-x and time so that the rate constant (K) is

concluded from the slope then t1/2 is calculated from the relation t1/2 = 1/k VA where K was found

to be 6.08*10-4 and t1/2 was found to be 197.3 minutes.

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Sources of errors

The value of R2 was found to be 0.8002,

Where this value shows that results aren’t very accurate or reliable so that the value is far from

one so that percentage of error is found.

Error can be due to errors in the prepared concentrations of used substances which can be

avoided by being accurate in preparing samples. Errors can also be found in used flasks and in

the titration process where the flasks should be made sure to be clean and dry so that no errors

occur. Errors in calculations and plotting graphs can also be found which can be avoided by

repeating the calculations to make sure each step is right.

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References

1. Britannica, T. E. (2021, april 16). activation energy. Retrieved from Encyclopaedia

Britannica: https://www.britannica.com/science/activation-energy

2. clark, j. (2013). ORDERS OF REACTION AND RATE EQUATIONS. Retrieved from

https://www.chemguide.co.uk/physical/basicrates/orders.html

3. Clark, J. (2016, january). HYDROLYSING ESTERS. Retrieved from chemguide:

https://www.chemguide.co.uk/organicprops/esters/hydrolysis.html

4. Hydrolysis of Esters. (2021, march 22). Retrieved from chemistry libretexts:

https://chem.libretexts.org/@go/page/68163

5. learning, l. (n.d.). reaction mechanisms. Retrieved from lumen learning:

https://courses.lumenlearning.com/boundless-chemistry/chapter/reaction-mechanisms/

6. Reusch, W. (2020, september 13). Molecularity and Kinetics. Retrieved from chemistry

libretexts:

https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Or

ganic_Chemistry)/Alkyl_Halides/Reactivity_of_Alkyl_Halides/

Alkyl_Halide_Reactions/Substitution_and_Elimination_Reactions_of_Alkyl_Halides/

SN1_Substitution_Reactions/Molecula

7. second order reactions. (n.d.). Retrieved from https://byjus.com/chemistry/second-order-

reaction/

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8. Theopold, P. F. (2020, july 17). Factors Affecting Reaction Rates (Kinetics). OpenStax

CNX. Retrieved from chemistry libretexts:

https://chem.libretexts.org/Courses/Oregon_Tech_PortlandMetro_Campus/OT_-_PDX_-

_Metro%3A_General_Chemistry_II/08%3A_Crash_Course_on_Kinetics

%2C_Equilibrium_and_Thermodynamics/

8.03%3A_Factors_Affecting_Reaction_Rates_(Kinetics)

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