Experiment 4

Carboxylic Acid and Its Derivatives

NAME ID NO.

1. ADIB BIN ARIFFIN 012020090097

1. DHILANDHIRANN A/L POOBALAN 012020092263

1. SUKHVEER SINGH A/L RAJINDAR SINGH 012020091421

1. HEMANAND NAIDU A/L ANBHANANTHAN 012020092340

1. AMOSSON A/L AUGUSTIN 012020091788

1. SHARVIN A/L SHANKER 012020091724

CARBOXYLIC ACID AND ITS DERIVATIVES

Introduction:

The important classes of organic compounds known as alcohols, phenols, ethers, amines and
halides consist of alkyl and/or aryl groups bonded to hydroxyl, alkoxyl, amino and halo
substituents respectively. If these same functional groups are attached to an acyl
group (RCO–) their properties are substantially changed, and they are designated
as carboxylic acid derivatives. Carboxylic acids have a hydroxyl group bonded to an acyl
group, and their functional derivatives are prepared by replacement of the hydroxyl group with
substituents, such as halo, alkoxyl, amino and acyloxy. The carboxylic acid derivatives can all
be hydrolysed to carboxylic acids. The specific reaction conditions are discussed in this
experiment.

Objectives

 To study the properties and reactions of carboxylic acid and its derivatives

Apparatus

 Beaker
 Dropper
 Test tubes
 Retort stand
 Tripod stand
 Measuring Cylinder
Chemical reagent

 Ice
 Ether
 Boiling Chips
 Litmus paper
 Stearic acid
 Benzoic acid
 Ethyl benzoate
 Glacial acetic acid
 Propanoyl chloride
 0.5 M HCL solution
 NaOH 10% solution
 NaOH 20% solution
 Distilled water

Method

A. Solubility of Carboxylic Acid

1. Nine clean and dry test tubes are prepared and labelled.
2. 6 drops of glacial acetic acid is added to 3 ml of each of the following solvents in the
labelled test tube: ether, water, NaOH 10% solution. The test tubes are shaken. If the
acid dissolves, one drop at a time is continue to be added, until the solution is saturated
or until the volume of liquid reaches 6 ml. The acid is classified as soluble, slightly
soluble or insoluble.
3. Step 2 is repeated using the same small amounts of benzoic acid and acetic acid.
4. The observation is recorded in a table. If the small amount used does not dissolve at all,
the mixture is discarded and the test is repeated with an even smaller amount. Classify
the acid as soluble, slightly soluble, or insoluble.
 B. Hydrolysis of Acid Chloride

1. Propanoyl chloride is added one drop at a time to 5 ml of water in the fume hood.
2. The temperature of the reaction is recorded.
3. After the reaction is completed, the solution is tested with litmus paper.
4. Observation is recorded.

Results

Solubility of Carboxylic Acids

Acid Solubility in
Ether Water 10% NaOH
Glacial acetic acid
Soluble Soluble Cloudy (Mildly
soluble)
Benzoic acid
Soluble Insoluble Soluble

Stearic acid
Soluble Insoluble Insoluble
 Acid Solubility in

Ether Water 10% NaOH

Glacial acetic acid

Benzoic acid

Stearic acid
Hydrolysis of Acid Chloride

Observation:

The temperature increased by the end of hydrolysis (from 25°c to 27°c). The product also
changed blue litmus paper to red .
Discussion

1. Identify either the process that occurred in Hydrolysis of Acid Chloride is

exothermic or endothermic. Why?

The reaction that occurs when the acid chloride is reacted with water is a very exothermic
reaction as steam gas is given off and propanoic acid is formed. The reaction is exothermic
because the energy given off by the formation of bonds is greater than the energy that is
used to break the bonds thus the reaction is exothermic. We call tell if a reaction is
exothermic if the temperature is increased.

2. What is the reason to test the solution with litmus paper?

The main reason why the solution was tested with the litmus paper is to test whether the
solution is acidic or basic. It was used to determine the acidity of the chemical solution.

3. Arrange the carboxylic acids in order of increasing solubility in water. Explain.

Stearic acid, Benzoic acid, Glacial acetic acid.

a. Glacial acetic acid - acetic acid is able to form many new hydrogen bonds to water
molecules and so this results in a highly favourable interaction, leading to the high
solubility of acetic acid in water
b. Benzoic acid - Benzoic acid is a monobasic aromatic acid, moderately strong, white
crystalline powder, very soluble in alcohol, ether, and benzene, but poorly soluble in
water.
c. Stearic acid - Stearic acid is a saturated fatty acid that can deposit on the surface in
special conditions. This acid is insoluble in water.
Conclusion

Therefore, the solubility of different carboxylic acids can be rationalized from the structure of the
carboxylic acid itself. Acetic acid soluble since their OH groups are able to solubilize their alkyl
chain which does not exceed five carbons. Stearic acid are insoluble in water because their
alkyl chain exceeds 5 carbons and the OH group cannot solubilize the long, bulky alkyl chain. A
good solvent for stearic acid would be organic solvents like ether, chloroform and carbon
tetrachloride. Benzoic acid is insoluble in water because the benzene ring, due to its stability,
cannot be solubilized by the OH group. Carboxylic acids also react with sodium carbonate
through deprotonation. Only acetic acid and benzoic acid give a reaction because these acids
have a lower pKa value than the conjugate acid of the base which is NaHCO3.Stearic acid do
not react with NaHCO3 because they have higher pKa values than the conjugate acid of the
base. This tells us that sodium bicarbonate is not strong enough to deprotonate both carboxylic
acids. The rule here is: an acid can be deprotonated by a base that has a conjugate acid with a
higher pKa.NaHCO3 can be used to separate a mixture containing a water insoluble carboxylic
acid. Na2CO3 is not effective because carboxylic acids react, therefore, no separation occurs.
Some carboxylic acids react with KMnO4 and are oxidized. Examples are lactic acid which is
oxidized to pyruvic acid and formic acid and oxalic acids which are oxidized to carbon dioxide
and water. Non-reducing acids include acetic acid. And for the last part of the experiment, the
molar mass of an unknown carboxylic acid may be determined by identifying how many COOH
groups are present and by computing its neutralization equivalent.
References

1. Britannica. 2021. Carboxylic Acid.

https://www.britannica.com/science/carboxylic-acid

Accessed on 1st May 2021.

2. Chem Libre Text. 2021. Properties of Carboxylic Acid.

https://chem.libretexts.org/Courses/Eastern_Mennonite_University/EMU
%3A_Chemistry_for_the_Life_Sciences_(Cessna)/15%3A_Organic_Acids_and_Bases_
and_Some_of_Their_Derivatives/15.04_Physical_Properties_of_Carboxylic_Acids

Accessed on 2nd May 2021.

3. Praxi Labs. 2021. Test for Carboxylic Acid.

https://praxilabs.com/EnglishContent/Final_Experiments_PDF/Chemistry/Organic-
Chemistry/tests-for-carboxylic-group-simulation.pdf

Accessed on 3rd May 2021.

 LAB REPORT EVALUATION FORM
Subject/ Code: FGS0071P
Lab Title: CARBOXYLIC ACID AND ITS DERIVATIVES
Group Members:
1. ADIB BIN ARIFFIN
2. DHILANDHIRANN A/L POOBALAN
3. SUKHVEER SINGH A/L RAJINDAR SINGH
4. HEMANAND NAIDU A/L ANBHANANTHAN
5. AMOSSON A/L AUGUSTIN
6. SHARVIN A/L SHANKER
4 3
CRITERIA EXCELLENT
Report was sent earlier or
Punctuality, on time. Followed all the
format, guidelines and format
language and provided. Use appropriate
neatness language with minimal
X2 grammatical errors. Report
Max = 8m produced was neat and
orderly.
Description or step-by-step
Procedure of the process is included in
X1 detail and in order, using
Max = 4m passive sentences, diagram
is included when necessary.
Raw data, including units,
Data Collection
are recorded in a way that
X2
is appropriate, clear and
Max = 8m
organized.
1. The data is analyzed in
an appropriate way and is
related to the objectives.
2. The discussions was
Data analysis made related to the theory.
and Discussions 3. Identifies sources of
X4 error and explains their
Max = 16m effects on results
4. Presents suggestions on
experiment improvement
and further studies to be
done.
1. Data is summarized in
the conclusion.
Conclusion 2. Conclusions are made
X1 based on the data (not wild
Max = 4m guesses or leaps of logic),
3. Conclusions are made
based on the objectives
NAME
GOOD
Report was sent 1 day late.
Followed all the guidelines
and format provided. Use
appropriate language with
minimal grammatical errors.
Report produced was neat
and orderly.
Description or step-by-step
of the process is included
but not very clear, using
passive sentences, diagram
is included when necessary.
Raw data, including units,
are recorded in a way that is
appropriate and clear.
3 of 4 of the "excellent"
conditions is met
3 of 4 of the "excellent"
conditions is met
2 1
AVERAGE
Report was sent 2 days late.
Followed all the guidelines
and format provided. Use
appropriate language with
significance grammatical
errors. Report produced
was averagely neat and
orderly.
General description was
provided but not really in
order, did not use passive
sentences.
Raw data, including units,
are recorded although not
as clearly or appropriately
as they might be.
2 of the 4 excellent
conditions met
2 of the 4 excellent
conditions met
ID NO.
012020090097
012020092263
012020091421
012020092340
012020091788
012020091724
NEEDS WORK MARKS
Report was sent 3 days late.
Guidelines and format were
not followed. Use
appropriate language with
significance grammatical
errors. Report produced
was not in order.
The description was not
complete, some parts are
missing, did not use passive
sentences.
Raw data, including units,
are not recorded in a way
that is appropriate and
clear.
1 of the 4 excellent
conditions met
1 of the 4 excellent
conditions met
4. Hypothesis is rejected or
accepted based on the
data.

Marks 40