Petroleum Engineering & Gas Technology Department

Module Subject: Organic Chemistry

Module Leader: Associate Prof. Tamer Tawhid
Name: Osama Hesham Sayed Eraky
ID: 131820

/Group: A1

CARBOXILIC ACIDS
Organic Chemistry Lab Report Three

Abstract
A carboxylic acid is an organic compound that contains a carboxyl group (C(=O)OH) as The general
formula of a carboxylic acid is RCOOH, with R referring to the rest of the (possibly quite large) molecule
as Carboxylic acids occur widely and include the amino acids (which make up proteins) and acetic acid
(which is part of vinegar and occurs in metabolism) (Robert C. Neuman, 2004). Salts and esters of
carboxylic acids are called carboxylates as When a carboxyl group is deprotonated, its conjugate base
forms a carboxylate anion while Carboxylate ions are resonance-stabilized, and this increased stability
makes carboxylic acids more acidic than alcohols, Carboxylic acids can be seen as reduced or alkylated
forms of the Lewis acid carbon dioxide; under some circumstances they can be decarboxylated to yield
carbon dioxide (Lawrence, 1996). These tests are very important to Differentiate between the carboxylic
acids and both alcohols and carbonyl compounds (acidity test), Explaining the values of acidity of the
carboxylic acids and their mode of reactions based on the resonance in the carboxylic group (COOH),
Discriminating the different acids based on some important individual tests. The Test are classified into
two types; general tests and special tests as the general tests are; The acidity Test, Functional group Test,
Esterification Test, Calcium Chloride Test & Iron Chloride Test while the special tests are Mercuric Chloride
Test, Resorcinol Test, Azo-dye Test, Phthaleine Test, Fluorescene Test & Unsaturation Test.

Table of Contents
1- Abstract .....................................................................................................................................1
2- Table of Contents ......................................................................................................................2
3- Introduction ..............................................................................................................................3
- Introduction to Carboxylic Acids .........................................................................3
- General Reactions .............................................................................................3
- 1. The acidity Test ...............................................................................................3
- 2. Functional group Test ......................................................................................4
- 3. Esterification Test ............................................................................................4
- 4. Calcium Chloride Test ....................................................................................4
- 5. Iron Chloride Test ...........................................................................................4
- Special Reactions ..............................................................................................4
- 1. Mercuric Chloride Test ....................................................................................4
- 2. Resorcinol Test ................................................................................................5
- 3. Azo-dye Test....................................................................................................5
- 4. Phthaleine Test ................................................................................................5
- 5. Fluorescene Test ..............................................................................................5
- 6. Unsaturation Test ............................................................................................5
4- Experimental Results/Discussion ............................................................................................6
- Unknown 1 .........................................................................................................6
- Unknown 2 ..........................................................................................................7
- Unknown 3 ..........................................................................................................8
- Unknown 4 ..........................................................................................................9
- Unknown 5 .......................................................................................................10
- Unknown 6 ........................................................................................................11
- Unknown 7 ........................................................................................................12
- Unknown 8 ........................................................................................................11
- Unknown 9 ........................................................................................................12
5- References ................................................................................................................................13

Introduction
Carboxylic acids are compounds which contain a -COOH group, their physical properties (for example,
boiling point and solubility) of the carboxylic acids are governed by their ability to form hydrogen bonds
as the higher boiling points of the carboxylic acids are still caused by hydrogen bonding, but operating in
a different way (an introduction to carboxylic acids, 2016).
HO
O
C C
HOOC
COOH
O
OH
HO
COOH

HCOOH

HO

COOH

COOH

Formic acid
Oxalic acid

COOH
OH

CH3COOH

Tartaric acid

Benzoic acid

Succinic acid

COOH
COOH

COOH

Acetic acid
Phthalic acid

Cinnamic acid

Salicylic acid

General Reactions
1. The acidity test
Carboxylic acids have a high value of both Ka & pka which indicate their relatively high acidity compare to
other organic compounds
The acidity strength is determined by two functions which are Ka, pKa where ka is the acid dissociation
constant noting that pKa is the negative log of Ka which means the stronger the acid is, the lower its Ka
value.

There are many factors that affects the value of Ka as it increases as the dissociation of an acid in water
increases as a result of the production of more hydrogen ions. Ka is affected also by electronic factors or
steric environment. Carboxylic acids contain carboxylic group (COOH) that may seem it contains both
carbonyl group & hydroxyl group but is was proved that it does not undergo neither reactions of carbonyl
groups not the reactions of alcohols
2. Functional group test
It is a test used to detect the acidity of the sample as acids reacts with sodium carbonate or sodium
bicarbonate with effervescences due to the evolution of carbon dioxide gas.

3. Esterification test
It is a test that acids react with alcohols in the presence of a dehydrating agent such as concentrated
sulphuric acid and gives esters and water as ester possess fruity odor and this reaction is By adding one
gram of a carboxylic acid to one ml of an alcohol then gradually adding few drops of concentrated
sulphuric acid then by heating the mixture in a water bath for 5-10 min then cool then pour into sodium
bicarbonate solution

4. CaCl2 Test (aliphatic-: oxalic, tartaric, and succinic)

This test is used to detect the aliphatic (oxalic, tartaric, and succinic) by adding a suitable amount of
neutral salt of an acid then add about one ml of iron chloride solution / calcium chloride solution & detect
the precipitation in case of calcium chloride solution; if no precipitate is formed on cold, scratch the walls
of the test tube with a glass rod, if there is still no ppt. forming, boil the solution.
5. FeCl3 Test
This test is used to detect the aromatic and succinic acids by adding a suitable amount of neutral salt of
an acid then add about one ml of iron chloride solution. It is observed the formation of either buff
[succinic, benzoic, cinnamic and phthalic acids or violet color (Salicylic acid)].

Special Reactions
1. Mercuric Chloride Test
This test is used to detect the formic acid by adding an suitable amount of mercuric chloride (HgCl2)
solution to a sample of formic sample, we will observe the formation of a white precipitate from the
mercuric chloride after and after heating this white precipitate changes into black precipitate due to
deposition of mercury (Hg).
2. Resorcinol test
This test is used to detect the Tartaric acid by adding a suitable amount of resorcinol solution to a sample
of Tartaric acid then gradually adding few drops of concentrated sulphuric acid and finally warm & you
will observe the formation of a violet red ring at the interface of the two layers
3. Azo-dye formation (distinctive of phenols)
This test is used to detect the Salicylic acid by dissolving one ml of aniline dissolved in concentrated
hydrochloric acid and cool it to be test tube no. 1. By taking a sutable amount of sodium nitrite and adding
in a test tube to be no.2. By dissolving the salicylic acid into one gram of sodium hydroxide solution in a
test tube to be no. 3. Finally, by pouring test tube 2 into test tube 1 and pouring test tube 1 into 3, you
will observe the formation of red azo-dye.
4. Phthaleine test
This test is used to detect the Phthalic acid by adding one gram of salicylic acid in a dry test tube then add
one gram of phthalic anhydride and then gradually adding few drops of concentrated sulphuric acid and
finally by adding this mixture into a solution of sodium hydroxide and you will observe the formation of a
bright red color.

5. Fluorescene test
This test is used to detect the Succinic acid by fusing a few crystals of resorcinol with the sample of Succinic
acid then gradually adding few drops of concentrated sulphuric acid and finally by adding this mixture into
a solution of sodium hydroxide and you will observe the formation of a green fluorescence.
6. Unsaturation test
This test is used to detect the Cinnamic acid by adding suitable amount of bromine water to a sample of
Cinnamic acid in a separate test tube and then shake well for a few minutes and you will observe the
discharge of the bromines orange color.

Reagent
Formic acid
Acetic acid
Oxalic acid
Tartaric acid
Succinic acid
Benzoic acid
Salicylic acid
Phthalic acid
Cinnamic acid

N.S. + FeCl3
red color
red color
Buff ppt.
Buff ppt.
Violet color
Buff ppt.
Buff ppt.

N.S.+ CaCl2
White ppt. immediately
White ppt. on scratching
White ppt. on boiling
-

Solution + KMnO4
Violet color discharges
Violet color discharges
Violet color discharges

Experimental Results/Discussion
Carboxylic Acids
Unknown 1
Physical Properties:
Appearance:
Color:
Chemical Reactions:
Test
Acidity test
FeCl3 Test
KMnO4 Test
Ester formation
HgCl2 test

Observation
Effervescence due to CO2
Red color
Violet color discharges
Fruity odor
White ppt formed

Unknown is: Formic Acid

Result
Carboxylic acid
Formic acid or acetic acid
Formic acid
Carboxylic acid
Formic acid
Write the structure: HCOOH

Carboxylic Acids
Unknown 2
Physical Properties:
Appearance:
Color:
Chemical Reactions:
Test
Acidity test
FeCl3 Test
KMnO4 Test
Ester formation
CaCl2 test
Unknown is: Acetic Acid

Observation
Effervescence due to CO2
Red color
Negative
Fruity odor
Negative

Result
Carboxylic acid
Formic acid or acetic acid
Acetic acid
Carboxylic acid
Acetic acid
Write the structure: CH3COOH

Carboxylic Acids
Unknown 3
Physical Properties:
Appearance:
Color:
Chemical Reactions:
Test
Acidity test
CaCl2 Test
KMnO4 Test
CaCl2 test

Observation
Effervescence due to CO2
Negative
Violet color discharges
White ppt. on scratching

Unknown is: Tartaric acid

Result
Carboxylic acid
Oxalic or tartaric acid
Oxalic or tartaric acid
Tartaric acid
Write the structure: C4H6O6

HO
COOH
HO
COOH

Carboxylic Acids
Unknown 4
Physical Properties:
Appearance:
Color:
Chemical Reactions:
Test
Acidity test
CaCl2 Test
KMnO4 Test
Fluorescein test

Observation
Effervescence due to CO2
White ppt. on boiling
negative
Green Fluorescein

Unknown is: Succinic acid

Result
Carboxylic acid
Succinic acid
Carboxylic acid
Succinic acid
Write the structure:

HOOC
COOH

Carboxylic Acids
Unknown 5
Physical Properties:
Appearance:
Color:
Chemical Reactions:
Test
Acidity test
CaCl2 Test
KMnO4 Test
Fecl3 test

Observation
Effervescence due to CO2
Negative
Negative
Buff color

Unknown is: Benzoic Acid

Result
Carboxylic acid
Acetic or benzoic
Acetic or benzoic
Benzoic or succinic
Write the structure: C7H6O2

COOH

Carboxylic Acids
Unknown 6
Physical Properties:
Appearance:
Color:
Chemical Reactions:
Test
Acidity test
CaCl2 Test

Observation
Effervescence due to CO2
Negative

KMnO4 Test

Negative

Phthalein test
Bromine water test
Azo dye
Unknown is: Salicylic acid

Negative
negative
Azo dye will form

Result
Carboxylic acid
Formic or Acetic or succinic
or benzoic or salicylic or
phthalic
Acetic or succinic or benzoic
or salicylic or phthalic
Negative
negative
Salicylic acid
Write the structure: C7H6O3

COOH
OH

Carboxylic Acids
Unknown 7
Physical Properties:
Appearance:
Color:
Chemical Reactions:
Test
Acidity test
CaCl2 Test

Observation
Effervescence due to CO2
Negative

KMnO4 Test

Negative

Phthalein test

Bright red color appears

Unknown is: Phthalic Acid

Result
Carboxylic acid
Formic or Acetic or succinic
or benzoic or salicylic or
phthalic
Acetic or succinic or benzoic
or salicylic or phthalic
Phthalic Acid
Write the structure:

COOH
COOH

Carboxylic Acids
Unknown 8
Physical Properties:
Appearance:
Color:
Chemical Reactions:
Test
Acidity test
CaCl2 Test
KMnO4 Test
Phthalein test
Bromine water test

Observation
Effervescence due to CO2
Negative
Violet discharges
Negative
Orange color descending
gradually

Unknown is: Cinnamic acid

Result
Carboxylic acid
Negative
Cinnamic acid
Negative
Cinnamic acid

Write the structure:

COOH

Carboxylic Acids
Unknown 9
Physical Properties:
Appearance:
Color:
Chemical Reactions:
Test
Acidity test
CaCl2 Test

Observation
Effervescence due to CO2
White ppt appears

KMnO4 Test

Violet color discharges at the

moment
Negative
Negative

Phthalein test
Bromine water test
Unknown is: Oxalic acid

Result
Carboxylic acid
oxalic or tartaric or succinic
acids
Oxalic acid
Negative
Negative
Write the structure:

HO
O
C C
O
OH

10

References list

an introduction to carboxylic acids. (2016). Chemguide.co.uk. Retrieved 26 November 2016,

from http://www.chemguide.co.uk/organicprops/acids/background.html
Lawrence, N. J. (1996). Aldehydes and ketones. p. 11.
Robert C. Neuman, J. (2004). Carbonyl Compounds: Ketones, Aldehydes, Carboxylic Acids.
University of California, Riverside.

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