Amanda Nadine V.

Lazo
19B
Experiment 4: Identification of an Unknown through Qualitative Analysis 01/03/19

Objectives:
 To use the qualitative tests to analyze an unknown sample.
 To be able to identify the unknown sample after the qualitative tests

Prelab Questions

1. Qualitative tests can be used to determine if there are functional groups in a

compound. The following information can be derived from these qualitative tests: the
solubility of the compound in water, its solubility in 5% NaOH, 5% NaHCO3, 5%
HCL, concentrated H2SO4, the saturation of the compound via ignition test, what
kind of haloalkanes are present, whether the molecule is an alkene or an alkyne,
whether there are 5 or 6 carbon atoms, the types of alcohols present, the presence of
esters, the presence of methyl ketones, ethanol, and methyl carbinols, and the
presence of aldehydes and ketones (1).

2. Order of Solubility tests:

o Water START
o 5% NaOH
o 5% NaHCO
o 5% HCl
o Concentrated H2SO4

Is the
sample
Liquid Solid
solid or
liquid?

Add 1 to 2 drops
Use a spatula tip

Add 1 mL of the test solution into a

test tube and shake vigorously.
Observe if the solution is
homogenous. Test the solution with
red and blue litmus paper if soluble
in water.

Start
 Soluble
Do a Litmus Test in Yes Nitrogen, Oxygen, or
No
water? compounds with until
4 carbons

Solubility in 5%
NaOH
No Yes

Solubility in 5%
Carboxylic acid or phenol
HCl Test

Solubility in
No Yes 5% NaHCO3
Test
Amine Yes
Solubility in No
H2SO4 Test

Phenol Carboxylic
acid
No Yes

Compounds with nitrogen,

Halides, alkene, Unsaturated hydrocarbons, or
and alkyls oxygen
 3. Functional Groups tests:

Name of Test Compounds/Functional Important chemical Indications for a

Groups Reactions Positive Result
Confirmed/Differentiated

Unsaturated
Ignition Test compounds: yellow
Unsaturated compounds vs Combustion flame and sooty
Saturated compounds smoke
Saturated
compounds: Yellow
flame, non-sooty
smoke
Haloalkanes Sn1 mechanism Formation of
Alcoholic Silver insoluble silver
Nitrate Test halides

Alkenes and Alkynes Oxidation Formation of vicinal

Baeyer Test diol

Tertiary and Secondary Sn1 mechanism Formation of alkyl

Lucas Test Alcohols with up to 5-6 carbon chlorides
atoms
Primary 
Chromic Acid Test aldehydes
Primary and Secondary Oxidation
Alcohols Secondary 
ketones

Green Precipitates
Phenols Purple,
Iron (III) Chloride Test Phenols and enols red, or green
complexes

Enols  red, tan,or

violet complexes
Esters Red-violet
Hydroxamic Acid Test complexes

Methyl Ketones, Ethanol, Haloform reaction Yellow precipitate

Iodoform Test Methyl Carbinols

2,4- Aldehydes and Ketones Precipitation Yellow red

Dinitrophenylhydrazine Precipitate
(2,4-DNPH) Test
Aldehydes Reduction Carboxylate and
Tollens’ Test silver mirror

Safety Data Sheet

 Chemical Properties,
Reagent Physical Properties Safety Precautions, and
Waste Disposal
Toluene Molecular weight: May cause irritation to
(C6H5CH3) 92.13g/mol eyes, and nose
BP:110.7 ˚C Do not inhale
MP: -95 ˚C Dispose of in proper
Benzene-like odor waste container
Colorless

Cyclohexane Molecular weight: Emits acrid smoke and

(C6H12) 84.162g/mol fumes when heated to
BP:80.7 ˚C decomposition, may cause
MP:6.47 ˚C irritation/ corrosion to
Colorless liquid, pungent skin, flammable, dispose
odor in proper waste container
t-butanol OH Molecular weight: May cause eye and skin
(C4H10O) 74.123g/mol irritation, do not inhale or
MP: 25.81 ˚C ingest, Dispose in non-
Colorless liquid halogenated waste
Camphor-like odor

Ethanol Molecular weight: May irritate skin or burn

(CH3CH2OH) 46.069g/mol eyes, may produce
OH BP: 78.2 ˚C irritating, corrosive or
H
MP: -114.14 ˚C toxic gases, dispose in
Colorless liquid, pleasant non-halogenated waste
odor, burning container
Acetone Molecular weight: 58.08 Vapor may be irritating to
(C3H6O) O g/mol the eyes and mucous
BP: 56.08 ˚C membranes, low toxicity
MP: -94.9 ˚C but irritating to mucous
Colorless liquid, fruity membranes, dispose in
odor, pungent, sweetish Halogenated organic
waste container
Ethyl acetate Molecular weight: Flammable, may cause
(C4H8O2) 88.106g/mol headaches, irritation or
BP: 77.1 ˚C eyes, skin and respiratory
o MP: -83.8 ˚C passages, dispose in non-
Colorless liquid, fragrant halogenated waste
o odor container

Benzaldehyde Molecular weight: Inhalation of vapor may

(C7H6O) O 106.124g/mol cause irritation to eyes,
H BP:178.7 ˚C Prolonged contact may
MP: -57.12 ˚C cause irritation to skin,
Colorless to yellow dispose in non-
liquid, bitter almond or halogenated waste
oil like odor container
Source: PubChem

Procedure:

Solubility tests:

Order of Solubility tests:

o Water START
o 5% NaOH
o 5% NaHCO
o 5% HCL
o Concentrated H2SO4

Is the
sample
Liquid Solid
solid or
liquid?

Add 1 to 2 drops
Use a spatula tip

Add 1 mL of the test solution into a

test tube and shake vigorously.
Observe if the solution is
homogenous. Test the solution with
red and blue litmus paper if soluble
in water.
Tests for Functional Groups:

1. Ignition test

Start

Put 1-2 drops of a liquid sample

onto the tip of the spatula and heat
in inner cone of Bunsen burner.
Observe smoke

2. Alcoholic Silver Nitrate Test

Start

Put 1-2 drops of liquid sample into a
test tube or dissolve a spatula tip of
solid sample in minimum amount of
ethanol and add 1-2 drops of
solution to test tube
Add 4-5 drops of ethanolic silver
nitrate test solution and observe for
formation of gray/white precipitate.
If no precipitate forms after 5
minutes, heat mixture on steam
bath.

*Disposal: dissolve in 2-3 drops of

5% nitric acid and then throw in
silver waste container

3. Baeyer Test

Start

Shake test tube vigorously and

Put a few drops of sample and a few observe formation of reddish-brown
drops of Baeyer test solution precipitate. Dispose in non-
(potassium permanganate) into a halogenated waste container.
test tube
 4. Lucas Test

Start

Put 2-3 drops of sample and 5-8

drops of Lucas’ reagent into test
tube. Shake vigorously and observe
formation of second phase. Dispose
in non-halogenated waste container

5. Chromic Acid Test

Start

Add 4-5 drops of Chromic Acid test

Put 1-2 drops of liquid sample or solution and shake vigorously.
spatula tip of solid sample into test Observe for the formation of blue
tube green precipitate. Dispose in
chromium Waste container

6. Iron(III) Chloride Test

Start

Put 1-2 drops of a liquid sample or

spatula tip of solid sample into test
tube. Add 4-5 drops of 2% iron (III)
chloride and observe for the
formation of a colored solution.
Dispose in non-halogenated waste
container
 7. Hydroxamic Acid Test
Start
Put 1-2 drops of sample in and
about 5-8 drops of hydroxamic test
solution into a test tube
Add 5-8 drops of ethanol if solution
becomes cloudy. Add 2 drops of 2%
iron (III) chloride and observe
formation of red-violet solution.
Dispose in non-halogenated waste
container.
8. Iodoform Test
Start
Dissolve 2-3 drops of sample in 8-10
drops of water in a test tube
Add 3-5 drops of 5% NaOH until
color disappears and continue
shaking solution. Dispose in
halogenated organic waste disposal
9. 2,4 – Dinitrophenylhydrazine test
Add a drop of 6M NaOH and heat
test tube in water bath until boiling
Cool down to room temperature
and add 2M HCl drop-by-drop until
the solution becomes acidic
Add 8-10 drops of 5% NaOH and
add KI/I2 solution drop-by-drop until
dark color persists. Shake solution
vigorously and observe formation of
precipitates.
Warm test tube in hot water bath to
60 ˚C if no precipitates form. If
dark color disappears add KI/I2
until dark color persists for 2
minutes
 Start

Add 5-8 drops of 2,4-DNPH test

Put 1-2 drops of liquid sample or
spatula tip of solid sample into test
tube
10. Tollens’ Test
solution and shake test tube
vigorously. Observe for formation of
precipitates if no forms, gently heat
the mixture for 30 second and shake
test tube. Dispose in non-
halogenated Waste container.

Start

Add a drop of liquid or spatula tip of

In a clean test tube pour 2 mL of
solid sample. Shake test tube
Tollens’ reagent.
vigorously and leave for 15 minutes.
Observe appearance of mirror
silver.

Warm the mixture in a water bath

at 30-45 ˚C for a few minutes if
no silver mirror forms.
Disposal: destroy Tollens’
reagent with small amount of
dilute nitric acid. Dispose in
Silver waste container.
References:

1. Yanza ERS. Survey of Organic Chemistry Laboratory Manual. Department of Chemistry,

Ateneo de Manila University; 2014.