SK0034 : ORGANIC CHEMISTRY

LABORATORY REPORT

TITLE : EXPERIMENT 5- CARBOXYLIC ACID AND ITS DERIVATIVES

DATE OF EXPERIMENT : 11 APRIL 2017

DATE OF SUBMISSION : 16 APRIL 2017

LAB DEMONSTRATOR : MADAM MEGAWATI YUNUS

TUTORIAL : 10

GROUP MEMBERS :

NAME MATRIC NO. TASKS

Danish Shazrein binti FS16160481 Materials and Apparatus,
Kaslan Procedure

Jane Ann Jumi FS16110364 Discussion

Mohd Syazwan Hilmy bin Cover, Introduction,

FS16110146
Mohd Ghazali Objective

Nurul Farhana binti Bahrin FS16110310 Results

Siti Aisah binti Amlan FS16110179 Conclusion, References

INTRODUCTION

Carboxylic acids are compounds that could possibly be considered as

having two functional groups rolled which is a carbonyl (C=O) group to which is
directly attached a hydroxyl (OH) group. The properties of these two
functionalities together seem to reinforce one another such that together they
give some properties that are very different from either group, even though their
independent chemical properties are at times retained. When the carbonyl group
is directly bonded to a hydroxyl group the compound is said to be a carboxylic
acid - RCOOH. In addition, carboxylic acids are present in the majority of
biological pathway. The reaction of carboxylic acid with a base will produce
carboxylate salt and water.

RCOOH + NaOH RCOO - Na+ + H2O

In the presence of water, the carboxylic acids don't dimerise. Instead,

hydrogen bonds are formed between water molecules and individual molecules
of acid. The carboxylic acids with up to four carbon atoms will mix with water in
any proportion. When you mix the two together, the energy released when the
new hydrogen bonds form is much the same as is needed to break the hydrogen
bonds in the pure liquids. The solubility of the bigger acids decreases very
rapidly with size. This is because the longer hydrocarbon of the molecules get
between water molecules and break hydrogen bonds. In this case, these broken
hydrogen bonds are only replaced by much weaker van der Waals dispersion
forces.

Many classes of compound can be determined by substituting the OH

group of the acid with other functional group. These compound are called
carboxylic acid derivatives. Example of carboxylic acid derivatives are acid halide
and ester.

OBJECTIVES

1. To study the chemical properties of carboxylic acids and its derivatives.

2. To predict the end product of the reaction.
MATERIALS AND APPARATUS

CHEMICALS APPARATUS
Ether Beakers
2.5 M NaOH Droppers
0.6 M AgNO3 Test tubes
Glacial acetic acid Thermometer
Benzoic acid Measuring cylinder
Stearic acid Blue litmus paper
Acetyl chloride

METHODOLOGY

A. Solubility of carboxylic acid

1 9 dry test tubes were labeled.

2 It was placed such that
i 3 mL of ether into test tubes 1, 2, and 3.
ii 3 mL of distilled water into test tubes 4, 5, and 6.
iii 3 mL of 2.5 M NaOH into test tubes 7, 6, and 9.
3 6 drops of glacial acetic acid were added to test tubes 1, 4 and 7.
4 The tubes were shaken. If the acid dissolved, glacial acetic acid was added
continuously one drop at a time, until the volume of the solution reached 6
mL.
5 The solubility of the solutions were observed and recorded.
6 Benzoic acid was added in small portions into test tubes 2, 5, and 8. The
test tubes were shaken after each addition until each solution was
saturated.
7 The observations were recorded.
8 Step 6 was repeated using stearic acid in test tubes 3, 6, and 9.

B. Hydrolysis of acid chloride

1 Acetyl chloride was added carefully a drop at a time to 5 mL of water in a

fume cupboard.
2 The temperature of the reaction was recorded.
3 After the reaction has completed, the solution was tested with blue litmus
paper.
4 1 mL of 0.6 M AgNO3 was added.
5 The observations were recorded.
RESULT

A. Solubility of Carboxylic Acids

 Test tube Observation

1. Ether + glacial acetic acid Soluble

2. Ether + benzoic acid Soluble

3. Ether + stearic acid Soluble

4. Distilled water + glacial Insoluble

acetic acid
5. Distilled water + benzoic Insoluble
acid
6. Distilled water + stearic Insoluble
acid
7. NaOH + glacial acetic acid Soluble

8. NaOH + benzoic acid Soluble

9. NaOH + stearic acid Insoluble

B. Hydrolysis of Acid Chloride

Solution Observation

Acetyl Chloride + water Temperature: 30C

Blue litmus paper turns red

Acetyl Chloride + water + AgNO3 Turns cloudy

DISCUSSION
This experiment has been conducted to study the chemical properties of
carboxylic acids and its derivatives and to predict the end product of the
reaction. Carboxylic acid with general formula RCOOH, where R is an alkyl or aryl
group, are organic compound with a carboxyl (carbonyl+hydroxyl) functional
group.

In experiment solubility of carboxylic acid, the result shows that test tube
1,4, and 7 showed glacial acetic acid is soluble in ether and in sodium
hydroxide(NaOH) but insoluble in water(H 2O). Test tube 2,5 and 8 showed
benzoic acid is soluble in ether, insoluble in water(H 2O) but soluble in NaOH. Last
but not least, test tubes 3,6 and 9 showed stearic acid is soluble in ether,
insoluble in H2O and NaOH. According to the theory in organic chemistry,
hydrocarbons below 4 carbons are soluble in water, 5 to 6 carbons may or may
not soluble in water and above 6 carbons is insoluble in water. Those with a
higher molecular weight are insoluble owing to the larger hydrocarbon portion,
which is hydrophobic. Carboxylic acid are weak acids, therefore they form salt,
RCO2-, Na+ and H2O when reacted with NaOH which are base.

Theoretically, the glacial acetic acid(CH3COOH) should be soluble in water

because it has only one carbon atom (other than the carbonyl carbon), so steric
hindrance provided by the methyl group is substantially low. This allows water
molecule to easily form bonds with the acetic acid molecules(hydrogen bonds).

CH3COOH + H2O CH3COO- + H3O+

Glacial acetic acid dissolve in NaOH because when it reacts with sodium
hydroxide, it will produce sodium acetate and water as shown below;

CH3COOH + NaOH CH3COONa- + H2O

Benzoic acid is insoluble in water because even though a base is primarily

made from water, it also contains other compounds such as ether or solvated
hydroxide, that soon get to work deprotonating the acid on contact. The reason
that deprotonating easily occurs in a base that is predominantly water is because
the additional compounds often contained in a base liquid cause the benzoic acid
to create sodium benzoate after deprotonation occurs. The benzoic acid quickly
vanishes into the aqueous layer at this time because it has effectively
transformed into a salt, which is perfectly capable of dissolving in water. When
benzoic acid reacts with NaOH, it will produce benzoate ion and water, as shown
below;

C6H5COOH(s) + NaOH(aq) C6H5COO-Na+(aq) + H2O(l)

Even though it is soluble in NaOH but still it depends on the molarity of the
benzoic acid because its also follow the same rules as mentioned above.

The solubility of stearic acid with H2O and NaOH matches with the theory but
the solubility of stearic acid with ether does not match with the theory. In theory,
the stearic acid is slightly soluble in ether but from the experiment, it shows that
stearic acid in soluble in ether. This may due to human error or sight limitations
which cannot determine properly the solubility of the mixture of solution. This
may also due to the contamination in the test tube that filled with stearic acid.

For the experiment of hydrolysis of acid chloride, acetyl chloride is added into
5 mL water in a fume cupboard and heated. The temperature was the measured
and tested with a blue litmus paper after the reaction has completed and this
resulted in the blue litmus paper turns red. This showed that the acetyl chloride
has turne into carboxylic acid. When the solution in added with 1 mL of 0.6 M
AgNO3 , it turns cloudy and thus prove that the solution has mainly become a
carboxylic acid because of the reaction between two reactants has produced an
insoluble salt.

Several precautions can be taken when doing this experiment. One of it is

acetic acid must be handled in the fume cupboard because of its smell that
cannot be smell directly. Proper protective equipment such as gloves and safety
glasses must be used throughout the experiment.
 QUESTIONS

1. Briefly explain the saponification of ester and draw a diagram

to show the apparatus set up for the reaction.

Saponification is an organic chemical reaction that utilizes an alkali to

cleave an ester into a carboxylic acid and alcohol. As we will see
shortly, the primary use for this reaction is during the production of
soap products. The terms ester, carboxylic acid, and alcohol are
functional groups. A functional group is simply a group of molecules or
atoms that we can easily identify in a compound.

CONCLUSION
 In conclusion, the structure of the compounds plays an important role in its
solubility. From the result, glacial acetic acid is soluble in ether and sodium
hydroxide (NaOH) but insoluble in water. Theoretically, glacial acetic acid should
be soluble in water because it has only one carbon atom. Other than that, from
the result, benzoic acid is soluble in ether and NaOH but insoluble in water
because it contains other compound such as ether. Lastly, stearic acid is soluble
in ether but insoluble in water and NaOH. However, the solubility of stearic acid
is not match with theory because of human error during the experiment. For the
hydrolysis of acid chloride, the result showed that the acetyl chloride turn cloudy
because it has become carboxylic acid solution. The objective is achieved.

REFERENCES
 Leicester Henry and Marshall Klickstein (2011) Organic chemistry.
Englewood Cliffs, N.J: Prentice Hall.
Milligan, D. E.; Jacox, M. E (2012) Organic Chemistry IUPAC Nomenclature:
Carboxylic Acids and Their Derivatives (2nd edition). Wiley, John & Sons,
Incorporated
N. N. Greenwood and A. Earnshaw (2010) March's Advanced Organic
Chemistry: Reactions, Mechanisms, and Structure. Wiley-Inter science, 6th
edition.
Roald Hoffmann and Robert Burns Woodward (2014). Chemical Properties
of Carboxylic acid. Verlag Chemie Academic Press
R. G. Parr and W. Yang (2012) The chemistry of Carboxylic acid and Ester.
Oxford University Press, New York
Tan Yin Toon and Sheila Shamuganathan (2015) Chemistry for
Matriculation (4th edition). Oxford Fajar Sdn. Bhd.