Exercise 2

QUALITATIVE TESTS FOR THE ELEMENTS IN ORGANIC COMPOUNDS

The predominant elements in organic compounds are carbon and hydrogen. The next common
elements are oxygen, nitrogen, sulfur, phosphorus, and the halogens (chlorine, bromine, and iodine);
while the less common ones are the arsenic, antimony, mercury, and other metals.
Carbon and hydrogens are detected qualitatively by heating a mixture of the given substance with
dry copper (II) oxide in a glass tube. The organic substance is oxidized, forming carbon dioxide and
water. The presence of carbon dioxide is indicated by the formation of a white precipitate of calcium
carbonate when the gaseous products are passed through a solution of lime water. The presence of
hydrogen is indicated by the formation of droplets of water in the cool end of the tube.
The presence of oxygen is tested with the use of ferrox paper which is prepared by soaking filter
paper in methanol containing equal amounts of ferric chloride and ammonium thiocyanate. In the
presence of oxygen-containing compounds, the complex FeCNS ++ gives a deep red colored solution as it
is distributed between the filter paper and the test compound. Solutions of compounds do not contain
oxygen remain colorless.
The detection of nitrogen, halogens, and sulfur is made difficult by the non-polar nature of
organic compounds since they do not ionize in solution to give ions of these elements. For this reason, it
is necessary to convert these elements into inorganic ions before making qualitative tests. The conversion
is done through fusion with metallic sodium which decomposes the organic compound, and soluble salts
of the above elements are formed. The reaction is represented by the equation:

fusion
Organic compound [C] {[H] [O] [N] [X] [S] +Na NaCN, NaOH, NaX, and Na2S
Note: X represents any of the halogens: Cl, Br, and I
The resulting ionic compounds are then tested qualitatively for the presence of nitrogen, sulfur,
and the halogens.
Nitrogen is usually detected by the formation of Prussian blue after the sodium fusion. Nitrogen
in cyanide form is converted to sodium ferrocyanide which produces Prussian blue (ferris ferrocyanide,
Fe4 [Fe(CN)6]3 with ferric chloride in acid solution. If the nitrogen in the given substance is in the form of
amino nitrogen (-NH2), heating with soda lime (a mixture of fused NaOH and CaO) will liberate ammonia
gas which is tested with moist red litmus paper.
The halogens are detected by the Beilstein test. An organic halogen compound imparts a green
color to the flame when burned upon the surface of a copper wire. The copper oxide formed from the
copper wire reacts with the halogens to form the cuprous halide which burns with a green flame. Another
test for the halogens is based on the formation of an insoluble silver halide upon treatment with silver
nitrate solution in the presence of dilute nitric acid. It is necessary to remove cyanide and sulfide ions by
boiling the original test solution with the dilute halogens. (Silver cyanide is white and silver sulfide is
black). The silver halide gives a white to yellow color.
The presence of sulfur is detected by the production of brownish-black lead sulfide when the test
compound is treated with lead acetate in the presence of acetic acid. Acetic acid prevents the formation of
other insoluble lead salts. With sodium nitroprusside, the sulfide ion produces a red-violet color which
fades somewhat readily, it being a delicate one.
In cases where there are strong evidences for the organic nature of a substance, qualitative tests
are done only for elements other than carbon and hydrogen.
Test Compounds: Apparatus/ Materials:
Glucose ignition tube
Acetone cork
Benzene cork borer
Ethyl alcohol bent glass tubing
Gasoline iron clamp
Urea iron stand
Chloroform Bunsen burner
Monochloroacetic acid small test tubes
5% albumin (freshly prepared) small cork stoppers
Filter paper
Test tube holder
Glass rod
Red litmus paper
Copper wire
Water bath (beaker)
Reagents:
Lime water
5% KCNS
5%FeCL3 ferrox reagent
Methanol
NaOH⋅CaO (2:1) solid mixture
1% AgNO3
5% HNO3
10% NaOH
5% lead acetate
PROCEDURE:
1. Test for carbon and hydrogen (for demonstration)
a. Mix thoroughly 4 grams of CuO and 2 grams of glucose. Place in a dry ignition tube.
b. Fit a cork with a bent glass tubing to the ignition tube. Dip the end of the glass tubing in 2
mL of clear lime water in a test tube. (See diagram of set-up apparatus for C and H test.)
c. Clamp the ignition tube and heat it over a moderate flame. Observe what happens to the
lime water. Compare it with the original lime water.

CuO, glucose Iron clamp

Ignition
tube

Bunsen
burner Glass tubing
Lime water
Iron stand

Set-up for Carbon and Hydrogen Test

2. Ferro x Paper Test for Oxygen
a. Prepare the ferrox paper by dipping 4 strips of filter paper into the ferrox reagent and
airdry on a watch glass.
b. Prepare 4 dry test tubes with the test compounds as follows:
Test tube #1- 15 drops acetone
Test tube #2- 15 drops benzene
Test tube #3- 15 drops ethyl alcohol
Test tube #4- 15 drops gasoline or kerosene
Cover each test tube until needed.
c. Put a piece of fry ferrox paper into each test tube. Observe the change in color of the test
compound and the ferrox paper.
3. Soda Lime Test for Amide Nitrogen
Place a pinch of urea and a small amount of soda lime in a dry test tube. Heat it over a
moderate flame and briefly note the odor of the vapors formed. Then immediately expose to
the vapors a piece of wet red litmus paper attached to one end of the glass rod. Note the
change in color of the litmus paper.
4. Test for Halogens
a. Beilstein Test
Make a small loop on one end of a copper wire and heat the loop in the Bunsen
flame until no more color is imparted on the flame. Cool the wire and dip it in
chloroform. Heat again in the Bunsen flame. Observe and record the color of the flame.
b. Silver Nitrate Test
To 1 mL of 1% monochloroacetic acid (CAUTION: Handle with care; very
corrosive) add 1-2 drops of 5% nitric acid and boil gently for a few minutes. Add 10
drops of 1% silver nitrate solution. Observe and record what happens to the solution.
 5. Lead Acetate Test for Sulfur
To 1 mL of 5% albumin (egg white), add 5 drops of 10% NaOH and 2 drops of 5% lead
acetate. Boil over a water bath. Observe what happens to the solution.

QUESTIONS
1. What chemical reaction are involved in the test for carbon and hydrogen?
2. What Is the role of CuO in the reaction?
3. Write the structural formula of acetone, benzene, ethyl alcohol, and the major compound of
gasoline.
4. What chemical reactions are involved in the soda-lime test?
5. What compounds are responsible for the results in the:
a. Beilstein test?
b. Silver nitrate test?
c. Lead acetate test?
DATA AND ANSWER SHEET

Name _________________________________________________ Date__________________

Class Schedule _________________________________________ Rating _________________
Group No. _____________________________________________

Exercise 2
Qualitative Tests for Elements

I. Results and Observations

Elements tested Name of test/ Test compound Observation/s
reagent used
1. Carbon and
hydrogen

2. Oxygen

3. Nitrogen

4. Halogen a.)

b.)

5. Sulfur
II. Answers to Questions
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 Exercise 3
SEPARATION AND PURIFICATION OF ORGANIC COMPOUNDS
CRYSTALLIZATION
Crystallization is a highly effective method for the purification of organic substances, provided
that the physical properties of a given compound permit its purification in this manner. It involves the
process of dissolving the material to form a saturated solution in a suitable solvent at an elevated
temperature, filtering while hot to remove any suspended insoluble particles, and letting crystallization
proceed.
A desirable solvent for crystallization has the following properties: 1) dissolves the solute readily
at an elevated temperature, but only sparingly at a lower temperature (room temperature); 2) gives no
chemical reaction with the solute; 3) is sufficiently volatile so that it may be removed easily from the
purified crystals.
Separation of crystals before the hot solution has all passed through the filter paper can be
prevented by preheating or continuous heating of the funnel. Preheating may be accomplished by passing
hot solvent through the funnel. Continuous heating may be done with steam, hot water, or electrical jacket
used with the funnel. The solution may be heated from time to time while filtration is carried out.
Crystallization involves three consecutive stages: 1) removal of impurities which may retard or
inhibit crystal formulation; 2) nucleus formation; and 3) encouragement of growth of crystals to visible
form.
When samples contain colored impurities that give rise to solutions and crystals that are
yellowish or brownish when they should be colorless or are of an off-color rather than a pure color, they
may be treated with decolorizing carbon (animal charcoal or bone black). The fine carbon particles
present a large, active surface upon which soluble colored substances which serve as impurities may be
adsorbed, particularly the polymeric, resinous and reactive by-products that appear in traces in most
organic reaction mixtures. The decolorizing carbon is added to the hot solution prior to filtration, and the
solution is kept hot for a brief period, shaken to wet the carbon, and filtered. Adsorption occurs very
rapidly, and no advantage is gained by boiling the suspension for several minutes. Animal charcoal is
actually less effective at a high than a low temperature, and the only reason for operating at boiling
temperature is to keep the substances being crystallized in solution. It is a mistake to use more
decolorizing carbon than is actually needed, for an excess may adsorb some of the sample and cause
losses. Removal of impurities which retard crystal formation may also be affected by solubility or
volatility differences.
Nucleus formation may be spontaneous or indirect. Spontaneous nucleus formation, usually at the
vicinity of the freezing point of the compound, is caused by the orientation and aggregation of sufficient
number of molecules which may give rise to a crystal nucleus. For organic substances which do not
crystalize readily even from saturated solutions, a small crystal of the pure material may be added to
induce the crystallization process—a technique known as “seeding.” Crystallization can be induced also
by scratching the sides or bottom of the container with a glass rod. The microscopic scratches in the glass
surface provide sharp edges upon which crystals growth may start.
Growth of the crystal may be encouraged by stirring or agitation. This practice results in
distribution of the nuclei throughout the solution. In supersaturated solutions, growth of crystals may be
inhibited as a result of restricted motion of molecules. In this case, crystallization is effected by seeding or
by scratching the sides of the vessel with a glass rod.
 The quality of the crystals obtained after the process is ascertained by melting point
determination. If found to be still impure, re-crystallization with fresh solvent may be necessary.

Test Compounds:
benzoic acid
sodium chloride
methylene blue
brown sugar

Reagents:
animal charcoal
5% nitric acid solution
1% silver nitrate solution
distilled water

Apparatus/Materials:
beaker
glass rod
wire gauze
tripod
Bunsen burner
test tube
medicine dropper
filter paper
ice
PROCEDURE
A.
1. In a beaker, prepare a mixture consisting of 1g benzoic acid, a pinch of NaCl and 10 drops of
methylene blue or congo red.
2. Add 100 mL distilled water and heat, while stirring.
3. When the benzoic acid has dissolved, add 0.5g of animal charcoal, and continue heating with
vigorous stirring.
4. Bring the solution to boiling and filter while still hot.
5. Collect 5 mL of the hot filtrate in the test tube labeled “slow cooling” and set it aside to cool
slowly.
6. Collect another 5 mL of the hot filtrate in a second test tube and submerge in a beaker of ice
water. Label this “rapid cooling: and set aside. Collect the remaining filtrate in another beaker
or flask.
7. Record observation of the following: the color of the filtrate, the size of the crystals formed in
rapid cooling and in slow cooling process.
8. Separate the crystals by filtration. Wash twice with cold distilled water. Spread crystals on a
filter paper on a watch glass and allow to dry. Cover with another piece of clean paper while
drying to protect form dust and other impurities.
9. Test for the completeness of the separation:
Dissolve a small amount of the purified crystals in 1 mL hot distilled water in a test tube.
Acidify with 1 drop of 5% nitric acid and add 2 drops of 1% AgNO 3. Observe and record the
result.

B.
1. Dissolve one gram of brown sugar in 25 mL distilled water in a beaker. Get 2 mL of this
solution in a test tube and set aside as control. Note the color of this solution.
2. Heat the remaining solution to nearly boiling. Add 0.5 gram of animal charcoal with constant
stirring. Continue heating and stirring for a few seconds. Filter the solution while still hot.
3. Transfer 2 mL of the filtrate in a test tube. Compare its color with that of control.

Questions
1. How are colored impurities removed from crystals?
2. Why is it necessary to filter the solution while still hot?
3. What are the methods of inducing crystal formation from solution?
4. What factors cause the difference in the size of crystals formed?
5. How is the completeness of separation of the benzoic acid crystals from sodium chloride known with
the addition of AgNO3 solution?
DATA AND ANSWER SHEET

Name _________________________________________________ Date__________________

Class Schedule _________________________________________ Rating _________________
Group No. _____________________________________________

Exercise 3
Separation and Purification of Compounds
Crystallization

I. Results and Observations

1. Description of mixture:

a. Before heating ____________________________________________________

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b. While heating ____________________________________________________
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2. Crystals formed in rapid cooling

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Crystals formed in slow cooling
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3. Solutions of purified crystals + 1-2 drops of 1% AgNO 3

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4.
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Exercise 4
Separation and Purification of Organic Compounds
Sublimation
The direct conversion of a substance from solid to gas without passing through the liquid state is
sublimation. As a process of separation, it can be applied when the components of a solid mixture differ
appreciably in their vapor pressures. It involves gentle heating of the mixture in a confined container until
particles of the solid escape into the vapor phase. When the vapors are condensed on a solid surface,
crystals of the component with high vapor pressure can be collected, with the component of lower vapor
pressure left in the container.
As a process of purification, it also depends on differences in volatility – that is, in cases when
the impurities can be volatilized. Less volatile or non-volatile impurities will remain as residue while the
sublimate is being formed.
Although sublimation is convenient to apply and requires less time, its applicability is limited. It
cannot be used for separation of compounds having similar vapor pressures.
Test Compounds: Apparatus/Materials:
Salicylic acid Evaporating dish
Sodium sulfate watch glass
Wire gauze
Reagents: tripod
5% BaCl2 solution Bunsen burner or hot plate
Distilled water test tubes
Filter paper
PROCEDURE
1. Place a mixture of 0.5gram salicylic acid and a pinch of sodium sulfate in a clean, dry
evaporating dish. Cover the evaporating dish with a watch glass.

2. Set up under the fumehood the evaporating dish with its contents on a tripod with wire gauze over
a Bunsen burner.
3. Heat gently with a low flame. Observe what happens inside the evaporating dish.
 4. Cool the set-up completely and describe the substance formed on the watch glass and the one left
on the evaporating dish.
5. Collect the substance formed on the watch glass by scraping off carefully into a clean piece of
paper. Get a pinch for use in step 6 and submit the rest to your instructor.
6. Dissolve the substance in 1mL hot distilled water in a test tube. Add 2 drops of 5% BaCl 2
solution. Observe and record the result.
7. Get a small amount of the substance left in the evaporating dish and dissolve in 1mL hot distilled
water in a test tube. Add 2 drops of 5% BaCl2 solution. Observe and record the result.

Questions
1. What properties do substances which undergo sublimation possess?
2. Which compound in the mixture is the sublimate? Which did not sublimate?
3. How do you interpret the results obtained in steps 4 and 5?
4. Write the chemical reaction/s involved/
DATA AND ANSWER SHEET

Name _________________________________________________ Date__________________

Class Schedule _________________________________________ Rating _________________
Group No. _____________________________________________

Exercise 4
Separation and Purification of Compounds
Sublimation

III. Results and Observations

1. Description of mixture:

a. Before heating ____________________________________________________

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c. Upon cooling:
Sublimate ____________________________________________________
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2. a. Sublimate crystals + H2O + BaCl2: ____________________________________________

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