Philippine Normal University

College of Teacher Development

Faculty of Science Technology and Mathematics

Qualitative Analysis of Organic Compound

Denilyn Madrid1, Renyrick Manaloto1, Carla Bianca Salutin1
1
FSTEM, CTD, Philippine Normal University, Taft Avenue, Malate, Manila

DATE PERFORMED: 06/22/2021

DATE SUBMITTED: 06/28/2021

Abstract

The purpose of this experiment was to identify the unsaturation, heterogeneous atoms, and
functional groups present in these unknown compounds by being familiar with their properties
and identity. In testing the functional groups’ unsaturation, Bromine water test and Baeyer's test
was used. Whereas for testing the functional group, each group has been tested in various tests
including sodium metal test, ester test, ceric ammonium test, acetyl chloride test, litmus test,
Phtalein dye test, Fehling's test, m-Dinitrobenzene test, etc. Then, using Lassaigne’s test, the
presence of atoms (specifically, nitrogen, sulfur, chlorine, bromine, and chlorine) was
determined. From these various tests, the reaction of certain saturated and/or saturated to a
reagent was known. An unsaturated compound decolorizes while a saturated compound doesn’t
change. Also, the functional group present on a compound was determined through the
formation of a precipitate, color changes, or when the reaction gives a certain smell. Lastly, it
was detected that the unknown element assigned to the researchers was chlorine; as it formed
a white precipitate that is soluble in ammonium hydroxide.

______________________________________________________________________________

Keywords: qualitative, unsaturation, organic compounds

Introduction

Chemists frequently use qualitative patterns of reactivity to identify the functional groups
of unknown compounds. This technique, qualitative analysis, was an especially
important tool for structure determination in the early days of organic chemistry
(Amherst.edu, n.d.). Chemists often deal with identifying compounds even those which
are unknowns and it is important that they are knowledgeable how to run tests and to
process identifying and working with these compounds.

The purpose of this experiment is to identify the unsaturation, heterogeneous atoms and
functional groups present in these unknown compounds by being familiar with their
properties and identity. As the qualitative analysis contributes an important aspect to
experimental organic chemistry, the knowledge about identifying the elements and the
functional groups existing in the unknown compounds has to be put to a test using
various methods in the simulation. To test the functional groups (test of unsaturation) we
will be using both the Bromine water test and Baeyer's test. Whereas in identifying the

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presence of atoms (nitrogen, sulfur, chlorine, bromine, and iodine) Lassaigne's test will
be utilized.

Methodology

In this laboratory experiment (simulation), we had tested various compounds and used
chemicals to run tests. The researchers had to make sure that when doing this experiment,
protective gears were worn (goggles, gloves, lab coat, etc.) all throughout the duration of the
experiment to protect the body from the hazards of chemicals used. Proper handling of
chemicals, glassware, and equipment was also observed.

In testing the functional groups’ unsaturation, Bromine water test and Baeyer's test are used. In
the Bromine water test, the bromine water will be added to the saturated compound and
unsaturated compound; shake well and wait until a reaction will happen. In Baeyer’s test, the
alkaline potassium permanganate will be added to the saturated compound and unsaturated
compound and wait again until a reaction will happen.

Whereas for testing the functional group, each group has been tested in various tests:

For the alcohol group, the researchers will do sodium metal, ester test (the glacial
acetic acid and conc sulfuric will be added to the sample; the sample in the test tube will
be placed into a water bath for 10 minutes and is placed into a beaker with cold water),
ceric ammonium test (the ceric ammonium nitrate will be added to a sample and wait
until it will react with alcohol), acetyl chloride test (calcium chloride will be added to the
sample to create a solution and then will be filtered, acetyl chloride will be also added
into the sample, a rod will be dipped to ammonium hydroxide and will be placed over the
mouth of the test tube containing the sample), iodoform test (few drops of iodine
solution will be added to the sample and dilute sodium hydroxide will be added too, the
test tube containing the solution will be put in hot water bath for 10 minutes), and Lucas
test (the Lucas reagent will be added to each of the three test tubes containing primary,
secondary and tertiary alcohols labelled A-C and is shaken very well).

For phenol: litmus test (the sample will be dropped to the moist blue litmus), ferric
chloride test ( the sample will be added to the neutral ferric chloride solution),
Liebermann's test (the sample and sodium nitrite will be combined and will be heated in
a bunsen burner to heat its contents for 10 minutes; let the contents to cool for another
10 minutes; sulfuric acid will be added to the test tube containing the solution), and
Phtalein dye test (phthalic anhydride and 2 drops of concentrated sulfuric acid must be
added to the sample, the solution will be put into an oil bath for 10 minutes and then will
be cooled for another 10 minutes; the solution will be transferred to the beaker).

For the Aldehyde group: Schiff's test (Schiff reagent will be added to the sample),
Tollen's test (silver nitrate, diluted NaOH, diluted ammonia solution, and few drops of
the sample will be added to the test tube; it will be placed to a hot water bath for 10
minutes), Fehling's test (Fehling's solutions A and B will be added to the sample and
was put in a hot water bath for 10 minutes), 2-4-Dinitrophenylhydrazine test
(2,4-Dinitrophenyl and rectified spirit will be put into the sample), sodium bisulfite test

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(the saturated solution of sodium bisulphite will be added to the sample, sealed with a
cork and it must be shaken well).

For ketone group: m-Dinitrobenzene test (the m-Dinitrobenzene will be added to the
sample as well as the diluted sodium hydroxide), sodium nitroprusside test (sodium
nitroprusside and NaOH will be added to the sample), 2-4-Dinitrophenylhydrazine test
(rectified spirit and 2,4-Dinitrophenylhydrazine will be added to the sample) sodium
bisulfite test (sodium bisulphite will be added to the sample and the test tube will be
sealed with cork before it is shaken well).

For Carboxylic acid: Litmus test ( the sample was added into a moist blue litmus),
sodium bicarbonate test, and ester test (where few amounts of ethyl alcoholand conc.
sulfuric acid will be added to the sample. The test tube will be put in a water bath for 10
minutes).

For the Amine group: solubility test (diluted HCl will be added to the sample to produce
soluble salts), litmus test (the sample was added into the moist red litmus paper),
carbylamines (few drops of ethyl alcohol will be added to KOH, and will be heated in
bunsen burner for 10 minutes; chloroform and drops of the sample will be added also
then heated for 10 minutes), azo-dye test (HCl will be added to the sample; diluted
sodium hydroxide will be added to test tube C containing B-naphthol; the three test tubes
labeled A-C will be put in an ice bath for 10 minutes; contents of test tube B containing
sodium nitrite will be poured into the test tube A containing the sample and the solution
will be put into test tube C).

There were also tests that will be conducted for the primary, secondary and tertiary
amines such as the nitrous acid test and Hinsberg test. In a nitrous acid test,
concentrated HCl will be added to primary amine while sodium nitrite is added to test
tube B and is placed in an ice bath for 10 minutes. The sodium nitrite in test tube B is
poured into the primary amine that produced bubbles of nitrogen gas. The same process
is repeated for both the secondary and tertiary amine yielding different results. On the
other hand, the process done in the Hinsberg test is also just the same as the primary
amine and repeated with the secondary and tertiary amine.

Few drops of 25% NaOH, water, and benzene sulphonyl chloride are added to each
amine and produced different reactions.

On the other hand, to determine the presence of atoms (nitrogen, sulfur, chlorine, bromine, and
chlorine), Lassaigne's test is used. In this laboratory experiment an unknown element is used
which has to be identified after conducting several tests: (1) detection of Nitrogen, (2) in the
detection of Sulfur using sodium nitroprusside test, the sodium nitroprusside will be added to
Lassaigne's extract; in lead acetate test, the acetic acid will be poured into the Lassaigne's
extract and followed by the addition of acetate, (3) the detection of chlorine using silver nitrate
test where the concentrated HNO3 will be poured to Lassaigne's extract and will be heated, and
the AgNO3 and NH4OH will be added to the solution, (4) the detection of bromine using silver
nitrate test the concentrated HNO3 must be poured to Lassaigne's extract and heated, and the
AgNO3 and NH4OH will be added to the solution; next is through carbon disulfide test where
the diluted HCl and carbon disulfide must be added to the Lassaigne's extract followed by the
addition of chlorine water, and lastly (4) the detection of Iodine using the silver nitrate test, the

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concentrated HNO3 will be poured into Lassaigne's extract and heated, and the AgNO3 and
NH4OH will be added to the solution; the other one to test the presence of iodine is the carbon
disulfide test where the diluted HCl and carbon disulfide will be added to the Lassaigne's extract
followed by the addition of chlorine water.

Results and Discussion

Test for Functional groups (test for unsaturation)

In this virtual experiment, the aim is to identify organic compounds with the use of the different
types of tests for unsaturation. In background, the hydrocarbons are classified as saturated and
unsaturated. Saturated hydrocarbons are known as having no multiple bonds of carbon-carbon
and commonly called alkanes. While unsaturated hydrocarbons are those with double or triple
bonds such as alkenes and alkynes which are known as having the least amount of hydrogen
atoms.

The two methods for detecting unsaturation are done in this virtual experiment and the results
are as follows:

In the Bromine water test, a few drops of bromine solution is added to both Test tube A and B. In
test-tube A, the red-brown color remains indicate that the organic compound present in test tube
A is saturated. The color does not change since saturated compounds such as alkanes do not
react with the bromine, hence no changes occur. In test-tube B, the red-brown color is
decolorized. Decolorization indicates that the compound is unsaturated; this is due to the
molecular bromine being consumed as it undergoes an addition reaction with unsaturated
hydrocarbons.

In Baeyer’s test, a few drops of alkaline potassium permanganate is added to both test tubes. In
test tube A, the pink color remains indicate that the compound present is saturated. The color
does not change since there is no reaction between potassium permanganate and saturated
hydrocarbons. In test tube B, the pink color is decolorized. Decolorization indicates that the
compound is unsaturated; this happens when potassium permanganate reacts with unsaturated
compounds, the pink color permanganate is destroyed in the reaction. Hence, decolorization
happened.

The summary of the results are presented in Table 1:

Observation

Type of Test Reagent Used

Test tube A Test Tube B
(Saturated Compound) (Unsaturated Compound)

Bromine Water Bromine Water The red-brown color was not The red-brown color
Test decolorized disappeared

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Baeyer’s Test Alkaline The pink color was not The pink color disappeared
𝐾𝑀𝑛𝑂4 decolorized

Table 1. Shows the comparison of observed results in two different organic compounds subjected to
two types of tests for unsaturation.

Test for functional groups (alcohol)

The organic compounds which have the -OH functional group are called alcohols. The aim of
the experiment is to identify the presence of alcohol in an organic compound through a series of
different tests and as follows:

In the Sodium metal test, the appearance of brisk effervescence is due to the release of
hydrogen gas when alcohol reacts with active sodium metal.

2𝑅𝑂𝐻 + 2𝑁𝑎 → 2𝑅𝑂𝑁𝑎 + 𝐻2 ↑

2𝐶𝐻3𝑂𝐻 + 2𝑁𝑎 → 2𝐶𝐻3𝑂𝑁𝑎 + 𝐻2 ↑

In the Ester test, carboxylic acid reacts with alcohol to produce a fruit-smelling ester, the
reaction is called esterification. This reaction is slow and needs to be catalyzed by sulfuric acid.

𝑅 − 𝑂𝐻 + 𝑅𝐶𝑂𝑂𝐻 → 𝑅𝐶𝑂𝑂𝑅 + 𝐻2𝑂

𝐶𝐻3𝑂𝐻 + 𝐶𝐻3𝐶𝑂𝑂𝐻 → 𝐶𝐻3𝐶𝑂𝑂𝐶𝐻3 + 𝐻2𝑂

In the Ceric ammonium nitrate test, the reaction between ceric ammonium nitrate and alcohol
forms a pink color precipitate due to the formation of alkoxy cerium (IV) complex

(𝑁𝐻4)2[𝐶𝑒(𝑁𝑂3)6] + 3𝑅𝑂𝐻 → [𝐶𝑒(𝑁𝑂3)4(𝑅𝑂𝐻)3] + 2𝑁𝐻4𝑁𝑂4

(𝑁𝐻4)2[𝐶𝑒(𝑁𝑂3)6] + 3𝐶𝐻3𝑂𝐻 → [𝐶𝑒(𝑁𝑂3)4(𝐶𝐻3𝑂𝐻)3] + 2𝑁𝐻4𝑁𝑂3

In the Acetyl chloride test, alcohol reacts with acetyl chloride that results in the formation of
ester and hydrogen chloride. The product hydrogen chloride on contact with ammonium
hydroxide forms white fumes ammonium chloride and ammonium hydroxide.

𝑅𝑂𝐻 + 𝐶𝐻3𝐶𝑂𝐶𝑙 → 𝐶𝐻3𝐶𝑂𝑂𝑅 + 𝐻𝐶𝑙

𝐻𝐶𝑙 + 𝑁𝐻4𝑂𝐻 → 𝑁𝐻4 𝐶𝑙 + 𝐻2𝑂

In the Iodoform test, when secondary alcohol is warmed with sodium hydroxide solution and
iodine, a yellow precipitate of iodoform is formed.

𝐶𝐻3𝐶𝐻(𝑂𝐻)𝐶𝐻3 + 𝐼2 + 2𝑁𝑎𝑂𝐻 → 𝐶𝐻3𝐶𝑂𝐶𝐻3 + 2𝑁𝑎𝐼 + 3𝐻2𝑂

𝐶𝐻3𝐶𝑂𝐶𝐻3 + 3𝐼2 + 4𝑁𝑎𝑂𝐻 → 𝐶𝐻𝐼3(𝑖𝑜𝑑𝑜𝑓𝑜𝑟𝑚) + 𝐶𝐻3𝐶𝑂𝑂𝑁𝑎 + 3𝑁𝑎𝐼 + 3𝐻2𝑂

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In the Lucas test, Lucas reagent is a mixture of zinc chloride and concentrated hydrochloric
acid. It reacts with primary, secondary, and tertiary alcohols at different rates. The Lucas reagent
forms cloudiness as it reacts with alcohol. Tertiary alcohols immediately form cloudiness,
secondary alcohols react slowly and give cloudiness after five minutes, and primary alcohols
need to be heated to form cloudiness.

Figure 1. Shows the chemical reaction of Lucas reagent with

primary, secondary, and tertiary alcohol

The summary of the results are presented in Table 2:

Functional group Type of Test Observation

present

Sodium metal test Release of brisk effervescence

Alcohols
Ester test The fruity smell indicates the presence of alcohol

Ceric ammonium nitrate The red color precipitate appeared

test

Acetyl chloride test White fumes formed

Iodoform test Yellow precipitate formed

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Tertiary alcohol Cloudiness appears immediately

Lucas test
Secondary alcohol Cloudiness appears within five minutes

Primary alcohol Cloudiness appears only heating

Table 2. Shows the observed results from different types of test for the alcohol group

Test for Functional group (Phenol)

Phenol is a hydroxyl group on an aromatic ring or the hydroxy derivative of aromatic

compounds. The aim of the experiment is to identify the presence of phenol in an organic
compound through a series of different tests and as follows:

In the Litmus test, phenol turns blue litmus to red. This indicates that phenol is acidic.

In the Ferric chloride test, the aqueous solution of phenol reacts with ferric chloride solution
which gives a colored complex.

3− +
6𝐶6𝐻5𝑂𝐻 + 𝐹𝑒𝐶𝑙3 → [𝐹𝑒(𝐶6𝐻5𝑂)6] (𝑣𝑖𝑜𝑙𝑒𝑡 𝑐𝑜𝑙𝑜𝑟 𝑐𝑜𝑚𝑝𝑙𝑒𝑥) + 3𝐻𝐶𝑙 + 3𝐻

In Liebermann’s test, phenol reacts with concentrated sulfuric acid and sodium nitrite to form a
yellow color quinone monoxime complex. With the addition of sulfuric acid, a deep blue
indophenol complex is formed. On a dilution with distilled water, a red color indophenol is
formed. And with the addition of sodium hydroxide, the color turns to a deep blue sodium salt
solution of indophenol.

Figure 2. Shows the overall chemical reaction in

Libermann’s test

In the Phthalein dye test, phenol upon heating with phthalic anhydride with the presence of
concentrated sulfuric acid it forms a colorless condensation compound called phenolphthalein.
With further reaction with dilute sodium hydroxide, the solution becomes pink in color due to the
compound called fluorescein.

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Figure 3. Shows the overall chemical reaction in the Pthalein dye test.

The summary of the results are presented in Table 3:

Functional Type of Test Observation

group present

Litmus test Blue litmus turns to red

Ferric chloride test Violet color is seen

With sulfuric acid A deep blue color is seen

Phenols
Liebermann’s test With distilled water The deep blue color turns to
red

With Sodium The deep blue color

hydroxide solution appears again

Phthalein dye test The pink color is seen

Table 3. Shows the observed results from different types of test for the phenol group

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Test for Functional group (Aldehyde)

Aldehyde contains a carbonyl group and has a structure RCH(=O). The aim of the experiment is
to identify the presence of aldehydes in an organic compound through a series of different tests
and as follows:

In Schiff’s test, Schiff's reagent is prepared by passing the sulfur dioxide into the solution of dye
fuchsin. The aldehyde abstracts sulfurous acid from the reagent and restores the pink color. The
coloration is due to the formation of complex compounds in the solution.

In Tollen’s test, Tollen’s reagent consists of a silver ammonia complex in an ammonia solution.
The aldehyde reacts with Tollen’s reagent to form a grey-black precipitate or the silver mirror.

𝑅𝐶𝐻𝑂 + 2[𝐴𝑔(𝑁𝐻3)2]𝑂𝐻 → 𝑅𝐶𝑂𝑂𝑁𝐻4 + 3𝑁𝐻3 + 𝐻2𝑂 + 2𝐴𝑔 ↓ (𝑠𝑖𝑙𝑣𝑒𝑟 𝑚𝑖𝑟𝑟𝑜𝑟)

2+
In Fehling’s test, the solution Fehling’s is a complex of 𝐶𝑢 . When aldehyde is treated with the
2+ +
solution of Fehling’s the 𝐶𝑢 is reduced to 𝐶𝑢 and the aldehyde is reduced to acids. During the
reaction, a red precipitate is formed.

Figure 4. Shows the overall chemical reaction in Fehling’s test

In the 2,4-Dinitrophenylhydrazine test, aldehyde readily reacts with 2,4-Dinitrophenylhydrazine

to yield a yellow precipitate.

Figure 5. Shows the overall chemical reaction in

2,4-Dinitrophenylhydrazine test

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In the Sodium bisulfite test, aldehydes combine with sodium bisulfite to form a crystallized
water-soluble product or the aldehyde bisulfite.

Figure 5. Shows the overall chemical reaction in

Sodium bisulfite test

The summary of the results are presented in Table 4:

Functional group
present Type of Test Observation

Schiff’s test Pink color is seen

Tollen’s test Shining silver mirror is formed

Aldehyde

Fehling’s test Red precipitate is formed

2,4-Dinitrophenylhydrazine Test Yellow or orange precipitate is

formed

Sodium bisulfite test White crystalline precipitate is

formed
Table 4. Shows the observed results from different types of test forthe aldehyde group

Test for Functional group (Ketones)

Ketones contains a carbonyl group and has a structure 𝑅2𝐶(= 𝑂). The aim of the experiment is
to identify the presence of ketones in an organic compound through a series of different tests
and as follows:

In the m-Dinitrobenzene test, the ketones readily react with m-dinitrobenzene that gives violet
colorization.

In the Sodium nitroprusside test, the anion of ketone formed by the alkali reacts with
nitroprusside ion to form a red-colored complex.

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− −
𝐶𝐻3𝐶𝑂𝐶𝐻3 + 𝑂𝐻 → 𝐶𝐻3𝐶𝑂𝐶𝐻2 + 𝐻2𝑂
2− − 3−
[𝐹𝑒(𝐶𝑁)5𝑁𝑂] + 𝐶𝐻3𝐶𝑂𝐶𝐻2 → [𝐹𝑒(𝐶𝑁)5𝑁𝑂𝐶𝐻3𝐶𝑂𝐶𝐻2]

In the 2,4-Dinitrophenylhydrazine test, aldehyde readily reacts with 2,4-Dinitrophenylhydrazine

to yield a yellow precipitate.

Figure 5. Shows the overall chemical reaction in

2,4-Dinitrophenylhydrazine test

In the Sodium bisulfite test, aldehydes combine with sodium bisulfite to form a crystallized
water-soluble product or the aldehyde bisulfite

Figure 5. Shows the overall chemical reaction in Sodium bisulfite test

The summary of the results are presented in Table 5:

Functional group
present Type of Test Observation

m-Dinitrobenzene test Violet color is formed which slowly fades

away

Ketones Sodium nitroprusside test Red coloration

2,4-Dinitrophenylhydrazine Test Yellow or orange precipitate is formed

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Sodium bisulfite test White crystalline precipitate is formed

Table 5. Shows the observed results from different types of test for the ketone group

Test for Functional group (Carboxylic acid)

Carboxylic acids structure contains a carbonyl functional group and hydroxyl. The aim of the
experiment is to identify the presence of carboxylic acids in an organic compound through a
series of different tests and as follows:

In the Litmus test, the carboxylic acid turns the blue litmus to red due to the hydroxyl present in
-COOH which is far more acidic than alcohol.

− +
𝑅𝐶𝑂𝑂𝐻 + 𝐻2𝑂 → 𝑅𝐶𝑂𝑂 + 𝐻3𝑂

In the Sodium bicarbonate test, carboxylic acid reacts with sodium carbonate solution to
produce carbon dioxide which can be seen in the form of brisk effervescence.

𝑅𝐶𝑂𝑂𝐻 + 𝑁𝑎𝐻𝐶𝑂3 → 𝑅𝐶𝑂𝑂𝑁𝑎 + 𝐻2𝑂 + 𝐶𝑂2 ↑ (𝑏𝑟𝑖𝑠𝑘 𝑒𝑓𝑓𝑒𝑟𝑣𝑒𝑠𝑐𝑒𝑛𝑐𝑒)

In the Ester test, the carboxylic acid reacts with alcohol in the presence of concentrated sulfuric
acid to form a fruity smell of ester. This process is known as esterification.

𝑅𝐶𝑂𝑂𝐻 + 𝑅𝑂𝐻 + 𝐻2𝑆𝑂4 → 𝑅𝐶𝑂𝑂𝑅 (𝑒𝑠𝑡𝑒𝑟) + 𝐻2𝑂

The summary of the results are presented in Table 6:

Functional group
present Type of Test Observation

Litmus test Blue litmus turns to red

Carboxylic acid
Sodium bicarbonate test Brisk effervescence is observed

Ester Test Fruity smell

Table 6. Shows the observed results from different types of test for the carboxylic acid group

Test for Functional group (Amines)

Amines structure contains the functional group − 𝑁𝐻2. The aim of the experiment is to identify

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the presence of amine groups in an organic compound through a series of different tests and as
follows:

In the Solubility test, amines are basic in nature and readily dissolves in mineral acids

+ −
𝐶6𝐻5𝑁𝐻2 + 𝐻𝐶𝑙 → 𝐶6𝐻5𝑁𝐻3 𝐶𝑙

In the Litmus test, amines are basic in nature which turns red litmus into blue.
+ −
𝐶𝐻3𝐶𝐻2𝑁𝐻2 + 𝐻2𝑂 → 𝐶𝐻3𝐶𝐻2𝑁𝐻3 + 𝑂𝐻

In the Carbylamine test, the primary amine is treated with alcoholic potassium hydroxide and
chloroform to form offensive smelling isocyanide.

𝑅𝑁𝐻2 + 3𝐾𝑂𝐻 + 𝐶𝐻𝐶𝑙3 → 𝑅𝑁𝐶 (𝑖𝑠𝑜𝑐𝑦𝑎𝑛𝑖𝑑𝑒) + 3𝐾𝐶𝑙 + 3𝐻2𝑂

In the Azo-dye test, the aromatic primary amines react with nitrous acid to form diazonium salts.
The product further undergoes a coupling reaction with B-naphthol to form an orange-colored
dye.

Figure 6. Shows the overall chemical reaction in the Azo-dye test

In the Nitrous acid test, primary, secondary and tertiary amines are used and reacted with
nitrous acid.

Primary aliphatic amines react with nitrous acid to yield nitrogen gas, which is seen as bubbles
+ −
in the reaction. 𝐶6𝐻5𝑁𝐻2 + 𝐻𝑁𝑂2 → 𝐶6𝐻5𝑁≡𝑁 𝐶𝑙 (𝑑𝑖𝑎𝑧𝑜𝑛𝑖𝑢𝑚 𝑐𝑜𝑚𝑝𝑜𝑢𝑛𝑑)

Secondary amines react with nitrous acid to form a yellow oily nitrosamine
𝑅2𝑁𝐻2 + 𝐻𝑂𝑁𝑂 → 𝑅2𝑁𝑁𝑂 + 𝐻2𝑂

Tertiary amines react with nitrous acid to form soluble nitrile salts
+ −
𝑅3𝑁 + 𝐻𝑂𝑁𝑂 → 𝑅3𝑁𝐻 𝑁𝑂2

In the Hinsberg test, primary, secondary, and tertiary amines are reacted with benzene sulfonyl
chloride in the alkaline medium

Primary amines react with benzyl sulfonyl chloride to produce substituted sulfonamide that

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contains acidic hydrogen and dissolve in medium

Figure 7. Shows the overall chemical reaction of

primary amines and benzyl sulfonyl chloride

Secondary amines form a substituted sulfonamide which is insoluble in alkali since it does not
have acidic hydrogen

Figure 8. Shows the overall chemical reaction in the Hinsberg test with the secondary amine

Tertiary amine forms a substituted sulfonamide which is insoluble in alkali since it does not have
acidic hydrogen.

Figure 9. Shows the overall chemical reaction

in Hinsberg test with tertiary amine

The summary of the results are presented in Table 7:

Functional group
present Type of Test Observation

Solubility test Amine dissolves in dilute HCl

Litmus test Red litmus turns to blue

Amines

Carbylamines test An offensive smell is produced

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Azo-dye test Formation of red dye

Primary amine Bubbles of nitrogen gas

Nitrous acid test

Secondary amine Formation of a yellow oily layer

Tertiary amine No visible change

Primary amine No precipitate. In addition to conc.

HCl, insoluble material is seen

Secondary amine Hinsberg test The precipitate is formed. It does not

dissolve in HCl

Tertiary amine The precipitate is formed. It dissolves

in conc, HCl
Table 7. Shows the observed results from different types of test for the amine group

Lassaigne’s test

The aim of this experiment is to detect the presence of nitrogen, sulfur, chlorine, bromine, and
iodine in the given sample.

The given sample for our group in the virtual experiment is element 4, upon doing the silver
nitrate test the observed change in the test tube is the formation of white precipitate that is
soluble in 𝑁𝐻4𝑂𝐻which indicates that element 4 is chlorine.

In the Silver nitrate test, during the preparation of Lassaigne’s extract, element 4 (chlorine)
reacts with sodium to form sodium chloride. Sodium chloride gives a white precipitate of silver
chloride with silver nitrate solution. The precipitate is soluble in ammonium hydroxide.

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Figure 10. Shows the overall chemical reaction in silver nitrate test
with chlorine using Lasseigne’s extract, nitric acid, and silver nitrate.

The summary of results are presented in Table 8:

Sample Identification Test Test Method Observation Interference

Detection of No observed Absence of

Nitrogen change Nitrogen

Detection of Sulfur Sodium No observed Absence of Sulfur

nitroprusside test change

Detection of Silver nitrate test Formation of white

Chlorine precipitate that is Presence of
Element 4
soluble in 𝑁𝐻4𝑂𝐻 Chlorine

Detection of Silver nitrate test

Bromine No observed Absence of
change Bromine
Carbon disulfide
test

Detection of Iodine Silver nitrate test

No observed Absence of Iodine
change
Carbon disulfide
test

Conclusion and Recommendation

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This virtual experiment and laboratory report aims to identify the different properties of
organic compounds. To find out these properties, different tests were performed which
specifically identifies the unsaturation, heterogenous atoms, and functional groups present in
the organic compounds. Based on the results, we can conclude that a saturated compound will
not change its color if it is added to bromine water or alkaline. However, there will be a
decolorization of an unsaturated compound if it is added to bromine water or alkaline. Then,
based on the observations from the conducted tests to know the functional groups present in a
compound, we can conclude that most of the functional groups were determined through
observation of decolorization and formation of precipitation. On the other hand, the observation
on the Ester test for the alcohol and carboxylic acid function group is the fruity smell released by
the reaction. Then, after we conducted a virtual Lassaigne’s Test we found out that the assigned
element to us (which is Element 4) is Chlorine. The element forms a white precipitate that is
soluble in ammonium hydroxide.
As we finished this laboratory report, here are some of the recommendations that we suggest
for further research:
● It is better to conduct the experiment on hand to also practice the laboratory
techniques.
● Be familiarized with the virtual simulation site to avoid technical errors.
● Explore more techniques or tests to identify the properties of the organic
compounds.
● Make sure that the researchers are well-informed about the organic compounds
including their common properties and functional groups before conducting the
experiment.

References

● amrita.olabs.edu.in,. (2014). Detection of Elements: Lassaigne's Test. from

amrita.olabs.edu.in/?sub=73&brch=7&sim=149&cnt=4

● amrita.olabs.edu.in,. (2015). Tests for the functional groups. from

amrita.olabs.edu.in/?sub=73&brch=8&sim=141&cnt=4

● Experiment 10—Qualitative Analysis(n.d). https://www.amherst.edu

● Jove. (n.d.) Identification of Unknown Aldehydes and Ketones. [Video File].

https://www.jove.com/science-education/11223/identification-of-unknown-aldehydes-and-
ketones

● Jove. (n.d.). Identifying Alcohols. [Video File].

https://www.jove.com/science-education/11228/identifying-alcohols

● Williamson, K. L., & Masters, K. M. (2011). Macroscale and microscale Organic

Experiments. In Macroscale and microscale organic experiments (6th ed). Boston, MA:
Cengage Learning.

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