Org Chem Lab Manual

EXERCISE 1
PROPERTIES THAT DISTINGUISH ORGANIC FROM INORGANIC

COMPOUNDS
The basic study of Organic Chemistry is largely concerned with the general properties of
organic compounds, their distinction from inorganic compounds and their chemical behavior
according to the functional group or groups present in them. Although the chemical principles
involved in the reactions of inorganic substances are fundamentally the same as those for the
reactions or organic substances, certain typical differences between organic and inorganic
substances need to be considered.
Organic compounds are unstable compared with most inorganic compounds. They are
combustible with many having no sharp melting points, decomposing and charring at
moderately high temperatures. Comparatively, few of them ionize because of the nature of the
bonds (covalent) that hold their atoms together in a molecule. Accordingly, they are mostly nonelectrolytes, with a few being weak electrolytes. They are practically insoluble in water and
other polar solvents.
Many organic compounds contain the same kind and number of atoms and yet, because
of differences in structure, they exhibit different sets of properties. This property, called
isomerism, is a rarity among inorganic compounds. Furthermore, organic chemical reactions
are notably slow, in contrast with organic ones. It is commonly observed in the laboratory that
inorganic reactions occur almost instantly upon putting them together, whereas even when
appropriate catalysts are employed, several hours may be required of organic compounds
before equilibrium of a reacting system is attained or an organic reaction is said to be
completed.
TEST SAMPLES
Ethyl alcohol
Distilled water
Sucrose (refined sugar)
NaCl (s)
Naphthalene
1M sucrose
1M NaCl
n-Hexane
Acetone
CaCO3
APPARATUS
REAGENT
Beakers (250 mL)
Petroleum ether
Evaporating dish
Test Tubes
Watch glass
Test tube holder
Bunsen burner
Crucible tong
metal bottle cap (w/o plastic lining)
PROCEDURE
A. Ignition Tests:
1. Flammability
a. Place 2 to 3 drops of ethyl alcohol in a watch glass. Touch the ethyl
alcohol with a lighted matchstick. Observe whether it is flammable or
non-flammable. Take note of the luminosity (color and amount of
smoke formed) if a flame is produced.
b. Repeat the test, using water instead of ethyl alcohol. Compare the
results obtained.
2. Charring
a. Place a pinch of sucrose in a dry soft drink bottle cap (plastic lining
removed). Hold firmly with a tong and heat over a moderate Bunsen
flame for one minute. Observe what happens and describe the substance left after heating.
b. Repeat the test, using a pinch of NaCl or CaCO3 instead of sucrose.
Record the observations.
B. Solubility Tests:
1.
Into 3 separate test tubes, place 1 mL each of distilled water. Add a

pinch of naphthalene to the first test tube, acetone to the second test
tube and NaNO3 to the third test tube. Shake for 2 minutes and note
your observation.
2. Repeat the test using petroleum ether instead of water. Record

observations.
NAME: ___________________ Date: ______________________

Group No. ________________ Class Schedule: _____________
Exercise 1
PROPERTIES THAT DISTINGUISH ORGANIC FROM INORGANIC
COMPOUNDS
I.
OBSERVATIONS AND RESULTS

NAME OF TEST
COMPOUND TESTED
1. Ignition Tests
a. Flammability
Ethyl alcohol
Water
b. Charring
Sucrose
Sodium chloride
Calcium carbonate
2. Solubility Tests
Naphthalene in water
Acetone in water
Sodium nitrate in water
Naphthalene in petroleum
ether
Acetone in petroleum ether
Sodium nitrate in petroleum
ether
OBSERVATION
II.
EXPLANATION OF RESULTS
1. Ignition Tests
a. Flammability
________________________________________________________________
b. Charring ___________________________________________________
2.
Solubility
___________________________________________________________________________
___________________________________________________________________________
__________________________________________
EXERCISE 2
QUALITATIVE TESTS FOR ELEMENTS INORGANIC COMPOUNDS
The predominant elements found 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 arsenic, antimony, mercury and other
metals.
Carbon and hydrogen 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 white
precipitate of calcium carbonate when 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 may be determined either with the use of ferrox paper or the
compound iron (III) hexathiocyanatoferrate (III) . Ferrox paper 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 FeSCN ++ gives deep red colored
solution as it is distributed between the filter paper and the test compound. Solutions of
compounds which do not contain oxygen remain colorless. On the other hand, iron (III)
ammonium sulfate and potassium thiocyanate together react to form iron (III)
hexathiocyanatoferrate (III). This compound dissolves in the presence of oxygen-containing
compounds to give a red to reddish-purple color. The reaction is shown below:
2Fe(NH4)(SO4)2 +6KSCNFe
Iron(III)ammonium
[Fe(SCN)6]+ 3K2SO4 + (NH4)2 SO4
Potassium
Potassium sulfate
Ammonium
sulfate
sulfate
thiocyanate
Iron(III)hexathiocyanatoferrate (III)
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:
Organic compound [C] [H] [O] [N] [X] [S] + N

Na2S
NaCN, NaOH, NaX and
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 the Prussian
blue (ferric 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 (- NH 2), 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 dilute
nitric acid; otherwise, these ions form precipitates, which interfere with the detection of the
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
Hexane
filter paper
REAGENTS
Lime water / Soda Lime
NaOH-CaO (2:1 solid mixture)
5% lead acetate
1% AgNO3
5% HNO3
10% NaOH
KSCN
Fe(NH4)(SO4)2
Toluene
Butanol
Napthalene
Benzoic acid
Nitric acid
test tube holder

glass rod
red litmus paper
copper wire
water bath (beaker)
CuO
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 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 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.
Iron clamp
Ignition tube
CuO & glucose
Bunsen burner
bent glass tubing
Lime H 2O
Figure 1. Set-up for Carbon and Hydrogen Test

2. Test for Nitrogen (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.
3. 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 1mL of 1% Monochloroacetic acid (CAUTION: Handle with care; very corrosive)
add 1-2 gtts of 5% Nitric Acid and boil gently for a few minutes. Add 10 gtts of 1% Silver
Nitrate solution. Observe and record what happens to the solution.
4. Test for Oxygen (Ferrox Test)

a)
In a dry test tube, carefully grind together with a stirring rod a crystal of Fe(NH 4)
(SO4)2
and KSCN; iron (III) Hexathiocyanatoferrate (III) will adhere to the stirring rod as a
colored mass.
b)
c)
In another test tube, dissolve 3 gtts of butanol in 1 mL toluene.

Stir the solution with the stirring rod holding the iron (III) hexathiocyanatoferrate
(III).
Record the result.
d)
Wash and dry the stirring rod, then repeat steps a to c, using hexane as test sample.
e)
Repeat d, but use 30 mg of the solid samples naphthalene and benzoic acid one
after
another. Record results.
5. Test for Sulfur (Lead Acetate Test)

To 1 mL of 5% albumin in a test tube, add 5 drops of 10% NaOH and 2 drops of 5% lead
acetate. Boil the mixture in a water bath. Observe what happens to the solution.
NAME: ___________________ Date: ______________________

Exercise 2
QUALITATIVE TEST FOR ELEMENTS IN ORGANIC COMPOUNDS
I.
ELEMENT
TESTED
NAME OF TEST
TEST
COMPOUND
OBSERVATIONS
1. Carbon &
Hydrogen
2. Nitrogen
3. Halogen
a.
b.
4. Oxygen
5. Sulfur
II.
INTERPRETATION OF RESULTS
(Do the test samples contain the elements tested for?)

1. Test for Carbon and Hydrogen
__________________________________________________________________________________
______________________________________________
2. Test for Nitrogen
__________________________________________________________________________________
______________________________________________
3. Test for Halogen

__________________________________________________________________________________
______________________________________________
4. Test for Oxygen
__________________________________________________________________________________
______________________________________________
5. Test for Sulfur

__________________________________________________________________________________
______________________________________________
III.
QUESTIONS:
1. What chemical reactions 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 hexane, naphthalene, butanol and benzoic
acid.
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? __________________________________________
EXERCISE 3
SEPARATION AND PURIFICATION OF ORGANIC COMPOUNDS
RECRYSTALLIZATION AND DECOLORIZATION

Recrystallization is a highly effective method for the purification of organic substances
that exist already as crystals. It involves the processes 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; and
3) is sufficiently volatile so that it may be removed easily from the purified
crystals.
Separation of the crystals before the hot solution has all passed through the filter paper
can be prevented by preheating or continuous heating of the funnel. Continuous heating may be
done with steam, hot water, or electrical jacket used with funnel. The solution may also be
heated from time to time while filtration is carried out.
Recrystallization involves three consecutive stages: 1) removal of impurities, which may
retard or inhibit crystal formation; 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 pure
color, they may be treated with decolorizing carbon (animal charcoal ~ a charcoal obtained by
the destructive distillation of animal matter at high temperatures; used to adsorb organic
coloring matter). 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 at 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 effected 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 recrystallize 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. Recrystallization can be induced also by scratching the sides or bottom of
a container with a glass rod. The microscopic scratches in the glass surface provide sharp
edges upon which crystal 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 SAMPLES:
APPARATUS/MATERIALS:
REAGENTS:
Benzoic acid
Sodium chloride
Methylene blue
Brown sugar
Beaker
Glass rod
wire gauze
Tripod
Bunsen burner
Test tube
Medicine dropper
Filter paper
Ice
Animal Charcoal
5% nitric acid
1% silver nitrate
distilled water
PROCEDURE
A. Recrystallization of Benzoic Acid
1. In a beaker, prepare a mixture consisting of 1g C6H5COOH, 0.1g of
NaCl and 2 drops of Methylene blue (C16H18N3SCl) .
2. Add 100 mL distilled water and heat, while stirring.
3. When the benzoic acid has dissolved, add 0.5g of powdered activated
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 a 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 of flask.
7. Record observations 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 the crystals on a filter paper on a watch glass and allow to dry.
Cover with another piece of clean paper while drying to protect from
dust and other impurities.
9. Test for the completeness of separation:
Dissolve a small amount of the purified crystals in 1mL hot distilled
water in a test tube. Acidify with 1 drop of 5% nitric acid and add 2
drops of 1% AgNO3. Observe and record the result.
B. Decolorization of Brown Sugar

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

powdered activated 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 the control.
NAME: ___________________ Date: ______________________

Exercise 3
Separation and Purification of Compounds
RECRYSTALLIZATION AND DECOLORIZATION
I.

1. Description of mixture:
a. Before heating ____________________________________________
___________________________________________________________
b. After heating _____________________________________________
___________________________________________________________
c. After filtration_____________________________________________
___________________________________________________________
2. Crystals formed in slow cooling _______________________________

___________________________________________________________
___________________________________________________________
Crystals formed in rapid cooling _______________________________
___________________________________________________________
___________________________________________________________
3. Solutions of purified crystals + 2 gtts of 1% AgNO3

___________________________________________________________
___________________________________________________________
4. Description of brown sugar:
a. Before heating ____________________________________________
___________________________________________________________
b. After heating _____________________________________________
___________________________________________________________
c. After filtration_____________________________________________
___________________________________________________________
II. A. Recrystallization of C6H5COOH ________________________________

___________________________________________________________
___________________________________________________________
B. Decolorization of brown sugar ________________________________
__________________________________________________________
__________________________________________________________
III.QUESTIONS
1. How was the colored impurities removed from the mixture? ________
___________________________________________________________
___________________________________________________________
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 are the factors that causes the differences in sizes of the
crystals formed? ____________________________________________
___________________________________________________________
___________________________________________________________
5.
How is the completeness of separation of the C6H5COOH crystals

from NaCl known upon addition of AgNO3 solution? ______________
___________________________________________________________
___________________________________________________________
___________________________________________________________
EXERCISE 4
SUBLIMATION
The direct conversion of a substance from solid to gas without passing through the
liquid state is known as sublimation. The process is convenient to apply, but its applicability is
limited. It cannot be used for separation of compounds having similar vapor pressures.
As a separation process, 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 the component with high vapor pressure changes into the vapor phase, while the
component of lower vapor pressure is left in the container. When the vapors are condensed on
a solid surface, the crystals of the component with high vapor pressure can be collected
separately.
As a purification process, it also depends on differences in volatility. Less volatile or
non-volatile impurities remain as residue while the sublimate is being formed.
TEST COMPOUNDS:
REAGENTS:
Salicylic acid
Sodium sulfate
evaporating dish
watch glass
wire gauze
tripod
Bunsen burner or hot plate
test tubes
filter paper
5%BaCl2
distilled water
PROCEDURE:
1. Place a mixture of 0.5 gram salicylic acid and a pinch of sodium sulfate
in a clean, dry evaporating dish. Cover the evaporating dish with a watch
glass.
2. Place the evaporating dish with its contents on a tripod with wire gauze
over a Bunsen burner or a hot plate inside the fume hood.
watch glass
Evaporating dish with the mixture
Hot plate
Figure 2. Set-up for Sublimation Process

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 1 mL hot distilled water in a test tube. Add 2
drops of 5% BaCl2 solution. Observe and record the result.

7. Get a small amount of the substance left in the evaporating dish and
dissolve in 2 mL hot distilled water in a test tube. Add 2 gtts of 5% BaCl 2
solution. Observe and record the result.
NAME: ___________________ Date: ______________________

Exercise 4
SUBLIMATION
I.
RESULTS AND OBSERVATIONS

1. Description of mixture:
a. Before heating ____________________________________________
___________________________________________________________
b. While heating _____________________________________________
___________________________________________________________
c. Upon cooling:
sublimate _______________________________________________
___________________________________________________________
___________________________________________________________
residue _________________________________________________
___________________________________________________________
___________________________________________________________
2. a. Sublimated crystals + H2O + BaCl2 :___________________________
___________________________________________________________
___________________________________________________________
b. Residue + H2O + BaCl2 :____________________________________
___________________________________________________________
___________________________________________________________
II.
QUESTIONS
1. What properties do substances which undergo sublimation
__________________________________________________________
process?
___________________________________________________________
___________________________________________________________
2.
Which compound in the mixture is the sublimate? Which did not

sublime?
__________________________________________________________
3. How will you interpret the results obtained in STEPS 4 & 5?
___________________________________________________________
___________________________________________________________
___________________________________________________________
4.
Write the chemical reaction/s involved.

__________________________________________________________
___________________________________________________________
___________________________________________________________
___________________________________________________________
EXERCISE 5
DISTILATION
The process of distillation is the procedure usually employed for the purification of liquid
organic substances. This involves the conversion of the liquid to the vapor state with the aid of
heat and condensation of the vapors back to the liquid state. The recondensed liquid is called
distillate.
A single, individual organic substance is readily purified with the ordinary distillation
apparatus which consists of a distillation flask fitted with a thermometer and water-cooled
condenser. Two or three pieces of broken porcelain chips are placed in the flask with the
substance to be distilled; they prevent bumping by producing a constant stream of bubbles
which keeps the liquid in motion. If the substance is quite volatile (low- boiling), the flask is
heated with a water batch. As the boiling point of every pure organic substance is constant at a
definite pressure, it is one of the most important criteria of purity.
The use of distillation is limited to a certain extent because some organic compounds
decompose when an attempt is made to distill them at normal atmospheric pressure. The
difficulty may be overcome by lowering the pressure over the substance, thus lowering the
boiling point and the temperature necessary to effect the distillation.
The types of distillation commonly employed are: 1) simple distillation; 2) fractional
distillation; 3) diminished-pressure distillation; and 4) steam distillation.
In simple distillation, a large temperature difference (more then 20 ) between the boiling
points of the components is necessary to obtain efficient separation. The component which is
more volatile will distill over first in almost pure form at a definite constant temperature and the
second component will distill over when the boiling point again remains constant for a long
period of time.
The distillation of a mixture of miscible organic liquids presents greater complexities
than that of a simple compound. The presence of one compound has a definite effect upon the
distillation of the others. Neither compound distills independently of the other; consequently,
the distillate contains a mixture of the two compounds. The boiling point of a mixture is not
constant, but changes during the distillation. The distillation of mixtures produces a vapor,
which contains a higher percentage of the lower boiling substance than that remaining in the
distilling flask.
The process of collecting separate fractions according to arbitrary boiling point ranges
during the distillation of a mixture of substances is known as fractional distillation. It is
performed readily by means of a special fractioning column. Repeated fractional distillation is
unnecessary when using a column since a multiple fractionation process takes place within the
column. The repeated volatilization and condensation within the column takes place in a very
good separation of the components of a mixture.
If the components of a mixture have boiling points very close together (within 1), it is
difficult to separate the mixture completely by fractional distillation. Some substances when
mixed, form a constant boiling mixture (azeotropic mixture) and it is impossible to separate
them by fractional distillation.
An azeotropic mixture is a mixture of liquids of certain definite composition that distills
at a constant temperature without change in composition. The boiling point is usually lower
than that of the highest boiling component, but is sometimes higher than that of the highest
boiling component; it is never of an immediate range. Ordinary ethyl alcohol is an azeotrope of
boiling point 78.1; composed of 95.5% (by weight) of ethanol, boiling point 78.4% and 4.5%
water, boiling point 100 .
TEST COMPOUNDS:
Acetone
Water
Quick fit distillation set-up
thermometer
Erlenmeyer flask
clamps
iron stand
electric hot plate
porcelain chips
evaporating dish
REAGENTS:
5% sodium nitroprusside
glacial acetic acid
5% NaOH
PROCEDURE:
A. Separation of Miscible liquids
1. Introduce 50 mL of a mixture containing 25 mL water and add 25 mL
Acetone into the distilling flask. Add three pieces of porcelain chips.
2. Prepare the distillation set-up. Refer to the diagram.
3. Have the set-up approved by the instructor before proceeding to the next step.
4. Heat with an electric hot plate and collect 5 mL of distillate at 56C and another 5 mL at
100 C.
B. Test for Completeness of Separation (to be done on both distillate fractions)

1. Place 2 3 gtts of the distillate in a dry evaporating dish. Ignite it with a lighted
matchstick.
2. Place 1 drop of the distillate in an evaporating dish. Add 1 gtt of the distillate in an
evaporating dish. Add 1 gtt of the 5% sodium nitroprusside and 1 gtt of 5% NaOH. Note
the color produced, then add 1 gtt of glacial acetic acid. Observe the change in color.
NAME: ___________________ Date: ______________________

Exercise 5
DISTILLATION
I.

Thermometer
Reading (C)
A. Volume of
Distillate
Collected
(mL)
B. Ignition
Test
NaNitroprusside
Test
N.A.
N.A.
Procedure A
1. 56 C
2. 100 C
Procedure B
Sample quantity
used:
___________
II.
INTERPRETATION OFRESULTS
Procedure A:_____________________________________________________
______________________________________________________________________
Procedure B:_____________________________________________________
______________________________________________________________________
III.QUESTIONS
1) What is distillation?
____________________________________________________________________________
____________________________________________________
2)
Why is this method effective in separating acetone from water? _________

________________________________________________________________
________________________________________________________________
3) What tests and experimental results indicate that acetone has been separated from
water? ____________________________________________
________________________________________________________________
4) What are the limitations of this method of separation? __________________
____________________________________________________________________________
____________________________________________________
5) Could the distillation process be used to convert muddy water to potable water? Explain
how and why? ______________________________________
________________________________________________________________
6) How will you separate the components of a mixture containing benzene, toluene and
water? _______________________________________________
________________________________________________________________
________________________________________________________________
________________________________________________________________
EXERCISE 6
EXTRACTION OF CHLOROPHYLL
A frequently used method of withdrawing or separating a substance from
Substance from a mixture is extraction by the use of solvents. In applying this method, the
mixture is dissolved in one of two immiscible solvents and then shaken with the other to
distribute the components between them. The amount of components in each of the two
solvents will be in direct proportion to their relative solubilities in each of them.
Water is usually one of the solvents used in an extraction process and the other solvent
is usually a non-polar organic liquid. Diethyl ether, one of the most important organic solvents,
is used extensively as an extracting solvent. It has high solvent power for hydrocarbons and for
oxygen-containing compounds. It is highly volatile (b.p. 34.60C ), so it is easily removed from
an extract at a low temperature that even sensitive compounds are not liable to decompose.
Although often preferred for research work because of these properties, ether is avoided in
industrial processes because of its being a fire hazard, losses in solvent recovery due to its
volatility and oxidation to peroxide on long exposure to air, which presents the hazard of
explosion.
Ether is slightly soluble in water ( 7.5% by weight ). Its efficiency as an extracting solvent
can be improved considerably by the addition of a small amount of an ionizable salt such as
NaCl to the water layer. The increase in polar property of the water solution will cause a
decrease in the solubility of the organic solute. This reduced solubility in water in the presence
of an electrolyte is referred to as salting-out effect. The bulk of water present in wet ether can
be removed by shaking the extract with saturated sodium chloride solution and drawing off the
lower layer. Drying is completed by filtering the ether solution with anhydrous sodium sulfate
which abstracts water by formation of the pentahydrate.
Alternative water-immiscible solvents are: petroleum ether, ligroin, benzene, carbon
tetrachloride, chloroform, methylene chloride, ethylene dichloride and n-butanol.
Extraction with water-immiscible solvent is useful for isolation of natural products that
occur in animal and plant tissues having high water content. For exhaustive extraction of
organic compounds from dried leaves or seeds, the solid is packed into a filter paper thimble
place in a soxhlet extractor. In soxhlet extractor, extractor, solvent vapor rises in the tube and
condensed solvent drops into the solid, leaches out soluble material and carries it to the boiling
flask where non-volatile extracted material accumulates. The same solvent is used over and
over and even substances of very slight solubility can be extracted by prolonging the operation.
REAGENTS:
Malunggay leaves
Beaker 250 mL
Distilled H20
Clean white sand
Separatory funnel
Filter paper
Funnel
Knife
Spatula
Anhydrous Na2SO4
hexane
PROCEDURE:
1. Remove the leaves of Malunggay from the stems.
2. Weigh 5 grams of it. Place in a mortar. Add a pinch of clean white sand and grind.
3. Add a mixture of 20 mL of hexane and 10 mL of methanol. Mix thoroughly.
4. Decant the liquid and filter.
5. Place the filtrate in a separatory funnel and add 30 mL of distilled water. Collect the green
extract in a beaker.
6. Dry the extract over a half spatula-full of anhydrous sodium sulfate for 2 minutes, and
then filter. Describe the color and consistency of the filtered extract.
7. Keep the extract in a clean sealed vial for use in the next experiment.
NAME: ___________________ Date: ______________________

Exercise 6
EXTRACTION OF CHLOROPHYLL
I.
RESULTS AND OBSERVATION
Color of extract ___________________________________________
_________________________________________
__________________________________________________________
__________________________________________________________
Other
II.
III.
descriptions
EXPLANATION OF RESULTS
______________________________________________________________________
______________________________________________________________________
_____________________________________
QUESTIONS
1) What are the indications that the desired substances have been extracted?
___________________________________________________________________
___________________________________________________________________
_________________________
2) Which solvent extracted chlorophyll from Malunggay?
_______________________________________________________
3) What is the role of methanol in the extraction of chlorophyll?
___________________________________________________________________
_____________________________________________
4) What is salting-out? When is it used in the extraction process?

___________________________________________________________________
___________________________________________________________________
__________________________________
EXERCISE 7
PROPERTIES OF ORGANIC COMPOUNDS
BOILING POINT
The boiling point of a substance is a physical constant that can be used in its
identification and characterization, as well as a criterion of its purity. Pure compounds have
constant boiling points, whereas mixtures show a boiling point range, except those special
constant-boiling ones called azeotropes.
Boiling point is defined as the temperature at which the vapor pressure of the substance
equals the pressure of the atmosphere above it. At this temperature, thermal energy overcomes
the intermolecular attractive forces holding the liquid molecules together, so they are separated
and escape into the atmosphere in the form of gaseous molecules.
Van der Waals forces of attraction are weak forces formed by induced polarization of
molecules as they acquire fluctuating charges caused by nearness of the molecules as they
vibrate. They come into play only within short distances and are usually observed among
hydrocarbon groups. The attractive force increases as the straight carbon chain is lengthened,
as there will be more fluctuating charges in those with longer carbon chains than those shorter
ones. Thus, more induced charges can draw molecules close to each other, increasing the
interaction.
Branching of the carbon chain lowers boiling point. Branching would not allow
molecules to approach each other close enough to allow interaction due to fluctuating charges.
Interaction is not as strong at large distances as it is short distances, especially in the case
where interaction depends on weal Van der Waals forces.
The hydrogen bond is a weak bond formed between a partially positive hydrogen H + and an
adjacent electronegative atom which bears a partial negative charge in the same or different
molecules. They are usually represented by dotted lines as shown in the following examples:
O
H
:
O
H
H
O
H
Intermolecular-bonding between water molecules
H
R-OH
O
O
H
H
H
O
H
Intermolecular-bonding between water molecules
There are two types of hydrogen-bonding: intermolecular and intramolecular.

Intermolecular H-bond can occur between any numbers of like or unlike molecules as long as
hydrogen donors and acceptors are present in a position in which they can interact. For
example, intermolecular hydrogen bonds can occur between NH3 molecules alone, between H2O
molecules alone, or between NH3 and H2O molecules, while intramolecular H-bonding can occur
within one single molecule, between two like molecules, or between two unlike molecules.
Intramolecular hydrogen bonds: Intramolecular hydrogen bonds are those which occur within
one single molecule. Intermolecular H-bond raises the boiling points of organic compounds,
while the presence of intramolecular H-bond in a compound lowers boiling points because of
the decreased tendency for interaction with other molecules.
Dipole-dipole interaction is observed among partly ionic or polar molecules. The charge
in this molecule is asymmetrical because there exists a small separation of charges on the
molecules: one end is slightly negative and the other end is slightly positive. The force of
attraction of a dipolar molecule or ion depends on how much charge is separated and how great
the separation is. The dipole moment of a molecule is a useful indication of the molecules
chemical and physical behavior. It result when two dipolar molecules interact with each other
through space. When this occurs, the partially negative portion of one of the polar molecules is
attracted to the partially positive portion of the second polar molecule. This type of interaction
between molecules accounts for many physically and biologically significant phenomena such
as the elevated boiling point of water.
In general, compounds involving ionic bonds have higher boiling points than covalent
compounds. This is because the amount of heat required to separate ions that are
electrostatically attracted is much higher than that required to separate molecules in covalent
compounds.
The presence of impurities may also affect the boiling point of a liquid. This is easily
understood if one has to recall that a liquid boils when its vapor pressure becomes equal to the
atmospheric pressure of the system. Non-volatile impurities usually decrease the vapor
pressure of the liquid, causing an increase in the boiling point. Volatile impurities usually
decrease the boiling point due to the increase in the vapor pressure.
TEST COMPOUNDS
n-butyl alcohol
tert-butyl alcohol
n-amyl alcohol
APPARATUS/MATERIALS
test tubes
beaker
percolator cups
thermometer
cork
hot plate
PROCEDURE:
1) Prepare the set-up apparatus for boiling point determination (see diagram below).
2) Place 4 mL of n-butyl alcohol in a dry ignition tube.

3) Insert the clean and dry percolator cup into the tube. Place the tube into the beaker with
oil. Clamp the ignition tube so that its bottom does not touch the beaker.
4) Adjust the height of the thermometer so that the mercury bulb is 2 3 mm away from the
opening of the percolator cup. Have the set-up approved by the instructor.
5) Heat moderately and then gradually adjust the knob of the hotplate to make it stronger so
as to cause a rise in temperature of 1 to 2 per minute. Stir the oil bath occasionally to
have uniform heating.
6) Record the temperature when the compound starts to boil (initial temperature, ti) and the
temperature (final temperature, tf ) when the temperature reading remains constant for a
few seconds. Note: Continue heating until after the constant boiling temperature has
been recorded.
7) Repeat boiling point determination with: a) n-amyl alcohol; b) tert-butyl alcohol, in place
of a n-butyl alcohol. Note: Always start with a cool oil bath.
NAME: ___________________ Date: ______________________

Exercise 7
BOILING POINT
I.
TEST COMPOUND
Name:
Structural formula:
Name:
BOILING POINT
(Experimental)
( C )
BOILING POINT
(Literature)
( C )
Structural formula:
Name:
Structural formula:
II.
a. Comparison
between
n-butyl
alcohol
and
n-amyl
alcohol
___________________________________________________________________
___________________________________________________________________
___________________________________________________________________
___________________________________________________________________
b. Comparison
between
n-butyl
and
tert-butyl
alcohol
___________________________________________________________________
___________________________________________________________________
___________________________________________________________________
_______________________
III.
QUESTIONS :
1. What indications did the experimental results gives regarding the purity of the
samples used?
___________________________________________________________________
_____________________________________________
2.
What may happen to the boiling point of the substance if there are
impurities present? Explain in terms of the nature of impurities?
___________________________________________________________________
___________________________________________________
3.
When are azeotropes formed? ______________________________
________________________________________________________
4.
What are the types of intermolecular attractive forces that hold

liquid molecules together? Differentiate them. ________________
___________________________________________________________________
_____________________________________________
________________________________________________________
5.
How do these intermolecular forces affect the boiling point of a

liquid? _________________________________________________
________________________________________________________
________________________________________________________
EXERCISE 8
PHYSICAL PROPERTIES OF ORGANIC COMPOUNDS
MELTING POINT
The melting point of a solid substance is the temperature at which the solid becomes a
liquid. At this temperature, molecular motion due to increased thermal energy is enough to
break down the lattice structure of the crystals. This temperature for a given crystal would
remain constant until all of the solid phase changes to liquid. Generally, solids with greater
cohesive forces exhibit higher melting points, while those bound by weak forces show low
melting points. These forces of attraction among molecules may also be Van der Waals forces,
hydrogen-bonding, dipole-dipole interaction or ionic forces.
Pure crystalline solids normally have sharp melting points. They undergo transition over
a temperature range of 1 or less. On the other hand, impure crystalline solids melt over a much
wider range of temperature. Thus, the melting point range, like the boiling point of a crystalline
compound is frequently used as an index of its purity. Most crystalline organic compounds
have characteristic melting points, which are easily determined and reproduced. This fact
makes melting point as well as boiling point the most widely used physical constant in
characterizing and identifying substances.
The lowering of the melting point by the addition of a small amount of one substance to
another is proportional to the relative molecular amounts of the two components in the mixture
and a function of the major constituent. It is thus possible to determine the molecular weight of
an unknown substance since this freezing point-lowering constant can be determined easily
and the amounts of the components (in grams) and the gram-molecular weight of the major
component are known.
APPARATUS
Capillary tubes
beaker
glass rod
iron stand
iron clamp
string
TEST COMPOUNDS
Stearic acid
Benzoic acid
Salicylic acid
PROCEDURE:
1. Seal one end of each of the capillary tubes (1mm diameter) by heating one of their tips.
2. Introduce powdered samples of stearic acid, benzoic acid and salicylic acid into three
separate prepared capillary tubes. This can be done by putting a small amount of the
sample (about 3-4mm in diameter) on a piece of clean dry paper and pushing the open end
of the capillary tube into the sample to scoop it. The sample may be shaken down to the
bottom by tapping on the side with fingers, dropping the tube vertically into a hard surface
several times, or the sample may be pushed to the bottom using a copper wire. Whichever
method is done to introduce the sample, the column of the solid should not be more than
1cm in the tube length and it should be tightly packed.
3. Fasten the capillary tube containing the sample to the thermometer by means of a piece of
string so that it is in contact with the thermometer bulb. Clamp the thermometer so that it
is centered in the beaker and submerged in the oil. See to it that the oil level is higher than
the height of the sample in the capillary tube.
4. Prepare the set-up for melting point determination. (Refer to the figure below.)
5. Heat the oil bath over a moderate flame. Then gradually increase the intensity of the flame
so as to cause a rise in temperature of 1 to 2 per minute. Protect the flame from air to
ensure a steady and continuous heating. Stir the oil bath occasionally to have a uniform
heating.
6. Record the temperature when the sample begins to melt and the temperature when the
entire sample in the capillary tube is completely melted. Note: Do not confusemelting point
with softening point.
7. Repeat step 3 to determine the melting points of the other samples. Note: Always start with
a cool oil bath.
8.
Complete the table by looking up in a reference book the correct melting
Points (lit) of the compounds.
NAME: ___________________
Date: ______________________
Exercise 8
MELTING POINT
I.
1. Test Compound: _______________ Structural formula _________________

Melting Point (Literature) __________ (Experimental) __________________
Explanation for Observed M.Pt. ____________________________________
_________________________________________________________
___________________________________________________________
_________________________________________________________
_________________________________________________________
___________________________________________________________
_________________________________________________________

_________________________________________________________
___________________________________________________________
_________________________________________________________
II.
Comparison of melting points:
1) Stearic acid and Benzoic acid _________________________________
_________________________________________________________
_________________________________________________________
2) Benzoic acid and salicylic acid _______________________________
_________________________________________________________
III.
QUESTIONS
1. What is the effect of impurity on the melting point of a substance?
_______________________________________________________
_______________________________________________________
_______________________________________________________
2. How can melting point and boiling point determinations are used in
Identifying and/ or characterizing unknown compounds?
_______________________________________________________
_______________________________________________________
_______________________________________________________
3. How do the observed melting points of the test compounds relate
with their structures?
_______________________________________________________
_______________________________________________________
_______________________________________________________
_______________________________________________________
_______________________________________________________
_______________________________________________________
EXERCISE 9
ALCOHOLS
Alcohols are compounds containing the hydroxyl (-OH) functional group bonded to an
alkyl, R and thus may be represented by the general formula ROH.
The reactivity of alcohols is mainly attributed to the -OH group. This functional group has
an inherited acid character shown when the hydrogen is released from the -OH bond. The ease
of removal is dependent upon the relative polarization of the -OH bond. The -OH group may also
be protonated at the oxygen, which weakens the C-O bond so that the whole group may be
cleaved off as water and subsequently replaced in the molecule.
Based on the alkyl group (R group represented by CH 3), the alcohol may be classified
into:
Some examples of these classes of alcohols are:
CH3CH2CH2OHCH3CH2CHOH
CH 3
n-propyl alcohol
sec -butyl alcohol

1-propanol
2-butanol
CH 3
CH 3C
OH
CH3
tert-butyl alcohol
2-methyl-2-propanol
The most commonly known primary alcohol is ethyl alcohol. It is the alcohol present in
alcoholic beverages. Ethyl alcohol or ethanol is obtained from the fermentation of sugars and
starches. The reaction is catalyzed by the enzyme zymase which is found in yeast.
Primary and secondary alcohols maybe distinguished from tertiary alcohols by the
chromic acid test. Primary alcohols are oxidized to aldehydes, while the secondary alcohols are
oxidized to ketones. This is indicated by the change in color of the solution from orange to
green.
Tertiary alcohol is not readily oxidized by the chromic acid because of the absence of
alpha hydrogen.
To further distinguished the different classes of alcohols, Lucas test is employed.
Tertiary alcohols react immediately to form an immiscible upper layer of alkyl chloride. The alkyl
chloride is insoluble in the medium and causes the solution to become cloudy before it
separates as a distinct layer. With secondary alcohols, the cloudiness appears after 5 minutes
while primary alcohols do not react under these conditions. The reaction mechanism involved
with tertiary and secondary alcohol is SN1.
R
l
R C OH
l
R
ZnCl2
HCl
R
l
RC+
l
R
R
l
R C Cl
l
R
H 2O
Alcohols may be classified based on the number of OH groups as monohydroxy or polyhydroxy

alcohols. Examples of polyhydroxy alcohols are:
CH2OH
l
CH2OH
Ethylene glycol
1, 2- ethanediol
CH2OH
l
CHOH
l
CH2OH
glycerol
1, 2, 3-propanetriol
The most important triol is glycerol. It is obtained as a by-product from the manufacture
of soap. It is used as a moisturizing agent in cosmetic formulation, in tobacco products and in
foods. Glycerol is detected by the acrolein test. Glycerol undergoes dehydration when heated
with KHSO4 to form propenal (acrolein), which has a pungent odor.
CH2OH
l
CHOH
l
CH2OH
Glycerol
+ KHSO4
HC=O
l
CH
l
CH2
+ 2H2O
acrolein or propenal
TEST COUMPOUNDS
APPARATUS
Glycerol
n-butyl alcohol
sec-butyl alcohol
tert-butyl alcohol
benzyl alcohol
methanol
isopropyl alcohol
test tubes
medicine dropper
beaker (water bath)
stop watch
Bunsen burner
thermometer
test tube holder
REAGENTS
5% K2CrO7
5 % H2SO4
Lucas reagent (HCl- ZnCl2 )
Acetic acid
Conc. H2SO4
KHSO4
distilled water
0.5 % resorcinol
copper wire
10% NaOH
Iodine solution
ether
PROCEDURE
1. CHROMIC ACID TEST
a.
b.
c.
Into 3 separates test tubes, place 20 drops each of the following: nButyl alcohol, sec-butyl alcohol, and tert-butyl alcohol, and label the test tubes
correspondingly.
To each test tube, add 3 drops of 5% potassium dichromate and 10 drops of 5% sulfuric
acid.
Place all the test tubes in a boiling water bath at the same time. Record the time required
for each solution to change color. Note the change in color and the odor of the product
formed.
2. LUCAS TEST
a.
b.
c.
Into 4 separate test tubes, place drops each of the following: tert-butyl alcohol, sec-butyl
alcohol, n-butyl alcohol, and benzyl alcohol.
To each test tube, add 20 drops of freshly prepared Lucas reagent. Shake only once and
let it stand.
Record the time required for the formation of an insoluble layer or emulsion in each of
the test tubes indicating the production of the alkyl halide.
3. ESTERIFICATION
a.
b.
Put 20 drops of methanol in a dry test tube. Add 10 drops of salicylic acid and 5 drops of
concentrated sulfuric acid to it.
Note the odor and the time required for the odor to develop.
4. TEST FOR METHYL ALCOHOL (REACTION WITH COPPER)

a.
Mix 10 drops of methyl alcohol with 10 drops of distilled water in a vial.
b.
c.
Heat a copper spiral in the Bunsen flame and dip into the methyl alcohol-water mixture.
Do these step 20-25 times.
Carefully add 1 drop of 0.5% resorcinol and 10 drops of concentrated sulfuric acid
allowing them to flow down along the side of the test tube. Note: Do not shake. Observe
the color produced at the junction of the two layers.
5. IODOFORM TEST
a.
b.
c.
To 4 drops of ethyl alcohol, add 4 ml of iodine solution. Then add drop by drop 10%
NaOH until the iodine is decolorized.
Place the test tube in a warmth bath (60C). Note the odor of the vapors and the color of
the precipitate formed.
Repeat the test with: 1) isopropyl alcohol, 2) methyl alcohol, in place of ethyl alcohol.
6. TEST FOR GLYCEROL

a.
b.
Solubility in water and ether.

Follow the procedure in exercise 10 to determine the solubility class.
Acrolein Test
Place 2 drops of glycerol in a dry test tube and add a pinch of KHSO 4. Heat the test tube
over the flame, note the odor produced.
7. FERMENTATION
d.
e.
U shaped glass tubing
Cork
b.
c.
Slice the overripe fruit (peel already removed) into chunks and osterized in an electric
blender.
Pass the puree into cheesecloth.
Measure the volume of the juice and add 5 grams of Bakers yeast for every 500ml of the
juice. Mix thoroughly.
Place the mixture in a 1 Liter Erlenmeyer flask. Cover with one-holed rubber stopper with
a U-shaped glass tubing.
Dip the other end of the glass tubing in 50 ml lime water and set aside the set-up for 5
days.
a.
Juice with yeast
Lime water
FERMENTATION SET-UP
f.
g.
h.
i.
Carefully separate the supernatant liquid from the residue by decantation.

Transfer the supernatant liquid to a 500 ml distilling flask. Add 2-3 pieces of boiling chips
and distill.
Collect the distillate when the temperature reaches 78-79C.
Test the distillate for the presence of ethanol using flammability test and chromic acid
test.
NAME: ___________________
Date: ______________________
Exercise 9
ALCOHOLS
I.

Name of Test
Compounds
1. CHROMIC ACID
TEST
n-butyl alcohol
sec-butyl alcohol
tert-butyl alcohol
2.
LUCAS TEST
n-butyl alcohol
sec-butyl alcohol
tert-butyl alcohol
benzyl alcohol
3.
ESTERIFICATION
METHANOL
Special Test for
Methanol
IODOFORM TEST
ethyl alcohol
isopropyl alcohol
methyl alcohol
4.
5.
6.
7.
Reagents
RESULTS
________________________
_
________________________
_
________________________
_
________________________
_
________________________
_
________________________
_
________________________
_
________________________
_
________________________
_
ACROLEIN TEST
glycerol
FERMENTATION
Flammability test
Chromic acid test
II. INTERPRETATION OF RESULTS

1. Chromic Acid Test
_______________________________________________________________
________________________________________________________________
2. Lucas Test _______________________________________________________________
________________________________________________________________
3. Esterification ________________________________________________________________
________________________________________________________________
4. Special Test for methanol

_______________________________________________________________
________________________________________________________________
5. Iodoform Test ________________________________________________________________
________________________________________________________________
6. Acrolein Test ________________________________________________________________
________________________________________________________________
7. Fermentation ________________________________________________________________
________________________________________________________________
III.
QUESTIONS
1. Compare the relative ease of oxidation of primary, secondary, and tertiary butyl alcohol
toward acid dichromate based on the time required for the solution to change color.
____________________________________________________________________________
____________________________________________________________________________
____________________________________________________________________________
2. What is the significance of the Lucas Test? Account for the reactivity of benzyl alcohol.
____________________________________________________________________________
____________________________________________________________________________
3. What is the significance of the Acrolein Test?
____________________________________________________________________________
____________________________________________________________________________
____________________________________________________________________________
4. Give one important commercial method of preparing ethyl alcohol in the Philippines.
Write chemical reaction involved.
____________________________________________________________________________
____________________________________________________________________________
____________________________________________________________________________
____________________________________________________________________________
____________________________________________________________________________
NAME: ___________________
Group No. ________________
Date: ______________________
Class Schedule: _____________
Exercise 10
SYNTHESIS OF ETHYL ALCOHOL

Chemical equation involved:
Data:
Volume of the distillate
% yield
Physical test
Color
Odor
Density
Boiling point
pH
consistency
Solubilities
Ether
Acetone
Chloroform
Distilled water
Chemical test
Combustion test
Lucas test
Calculation/s
Question/s:
1) What concentration range of ethyl alcohol is considered bactericidal?
2) What is the mechanism of action of the ethyl alcohol?
Conclusion:
EXERCISE 11
PHENOLS
Phenols are aromatic compounds with the OH group directly bonded to the
benzene ring. In the IUPAC system, monohydric phenols are named as derivatives of
phenol and located numbers are used to designate positions. Some examples of
phenols are.
Phenols are cresols are obtained from coal tar. Phenol is prepared in the
laboratory by the diazotization of primary aromatic amines.
The acidic character of the OH group is very well observed in the phenols.
Phenols are more acidic than alcohols due to resonance stabilization. The negative
charge of the conjugate base, the phenoxide ion is delocalized through the benzene
ring making it quite stable for the easy release of the H+ from the OH group.
The presence of electron-withdrawing group such as NO2 or CN on the ring can
further enhance the acidity.
Phenols react with dilute aqueous sodium hydroxide to form phenoxide salts.
These phenoxide salts are water soluble in contrast to phenols which are only slightly
soluble.
Phenols, react with ferric chloride to give a purple colored compound. This is due
to the formation of a ferric phenoxide salt that absorbs visible light to give an exited
state in which electrons are delocalized over both the iron atom and the conjugated
organic system.
The hydroxyl group in phenol is an activating group. It enhances an electrophilic
attack at the ortho and para position of the benzene ring. This is illustrated in the
bromination of phenol. A white precipitate of 2,4,6- tribromophenol is produced in the of
protic solvents ( solvents that can release protons ).
TEST SAMPLES
APPARATUS
1% phenol
1% thymol
1% cathecol
1% alpha naphthol
1% salicylic acid
Phenol ( conc. )
5% albumin
test tubes
glass rod
graduated cylinder
medicine droppers
Bunsen burner
beaker ( water bath )
REAGENTS
5% NaOH
Phthalic anhydride
5 % HCl
1% FeCl3
Bromine water
conc. H2SO4
distilled water
1% albumin
Millons reagent
I. PROCEDURE
1. SOLUBILITY IN ALKALI
Transfer 3 ml of 5% NaOH in a test tube and add a little phenol. Shake and
observe.
2. REACTION WITH FERRIC CHLORIDE
a. Into 4 separate test tube, add 1 ml of each of the following: 1% phenol, 1%
cathecol, 1% thymol, and 1% naphthol.
b. To each test tube, add 1 drop of 1% FeCl3. Note the color produced
3. BROMINE WATER TEST
Into 2 separate test tubes, place 1 m each of the following: 1% phenol and 1%
salicylic acid. To each test tube, add bromine water drop by drop until a precipitate is
formed. Compare results obtained.
4. PHENOLPHTHALEIN FORMATION
a. In a dry test tube, mix 2 drops of phenol and a pinch of phthalic anhydride. Then
add 3-4 drops of conc. H2SO4. Heat over a low flame until it is melted. Cool. Add 5
ml of distilled water and shake well.
b. Test the resulting solution for its indicator properly by adding 2-3 drops in
separate test containing 2 ml of 5% NaOH and 5% HCl, respectively. Note the color
formed in each test tube.
5. MILLONS TEST
Into 2 separate test tubes, place 1 nl of each of 1% phenol and 5% albumin. Add 6
drops of Millons reagent. Shake. Boil in a water bath. Note the color produced.
NAME: ___________________ Date: ______________________

Exercise 11
PHENOL
I.
II.INTERPRETATION OF RESULTS
1. Solubility in alkali
____________________________________________________________________________
____________________________________________________________________________
________________________________________
2. Reaction with FeCl3
________________________________________________________________
____________________________________________________________________________
____________________________________________________
3. Bromine water test
____________________________________________________________________________
____________________________________________________________________________
________________________________________
4. Phenolphthalein formation
____________________________________________________________________________
____________________________________________________________________________
________________________________________
5. Millions Test
____________________________________________________________________________
____________________________________________________________________________
________________________________________
III.
QUESTIONS
1. Explain why Br replaces Hs at the 2,4, 6 positions in its reaction with phenol.
____________________________________________________________________________
____________________________________________________________________________
________________________________________
____________________________________________________________________________
____________________________________________________________________________
________________________________________
2. Write the reaction involved in the formation of phenolphthalein. Identify the functional
group in phenolphthalein, which is responsible for the indicator property?
____________________________________________________________________________
____________________________________________________________________________
____________________________________________________________________________
____________________________________________________________________________
________________
____________________________________________________________________________
____________________________________________________________________________
________________________________________
3. What is the significance of Millons Test?
____________________________________________________________________________
____________________________________________________________________________
________________________________________
____________________________________________________________________________
____________________________________________________________________________
________________________________________
EXERCISE 12
HYDROCARBONS -- STRUCTURES AND CHEMICAL PROPERTIES

Objective:
-
To study the chemical and physical properties of hydrocarbons.
Background:
In this experiment you will observe the solubility (a physical property) and the chemical
reactivity of three different groups of hydrocarbons: alkanes, alkenes and aromatic compounds.
Hydrocarbons are organic compounds that contain only carbon and hydrogen. They are
extremely important to our society because so many products are derived from them: fuels,
fabrics, plastics, antifreezes, anesthetics, insecticides, to name a few. The major source of
aliphatic hydrocarbons is petroleum, an extremely complex mixture of compounds. Each of us,
on the average, uses several tons of petroleum each year (directly or indirectly), mostly for fuel.
Aromatic hydrocarbons are mainly obtained from coal, although small amounts are also
obtained from petroleum.
The solubility of a substance (the solute) in a solvent is the most important chemical
principle underlying three major techniques: crystallization, extraction, and chromatography.
Solubility can generally be predicted based on the like dissolves like rule. This means that
polar compounds dissolve in polar solvents and nonpolar compounds dissolve in nonpolar
solvents. This rule works because solubility is based on intermolecular forces, and these
forces can occur between molecules of the same compound, or between molecules of different
compounds. So, compounds with similar intermolecular forces will form solutions. Recall that
polar compounds have dipole-dipole interactions, while nonpolar compounds have dispersion
forces, which are much weaker. When discussing a liquid being mixed with another liquid (as in
this experiment), it is sometimes more appropriate to say that the compound and the solvent
are miscible. Likewise, if the liquid organic compound is insoluble in the solvent, then they are
immiscible. You will test the solubility of the three types of hydrocarbons in water and in
dichloromethane.
Each of the three classes of hydrocarbons has different chemical reactivity. Alkanes are
relatively unreactive because they have strong, nonpolar covalent bonds. Also, since they are
already completely saturated, they cant undergo addition reactions. Aromatic hydrocarbons
are also relatively unreactive, but for a different reason. They have a special stability due to
resonance (their pi electrons are completely delocalized). Aromatic compounds do not undergo
addition reactions, because they would lose this special stability. Alkenes, however, are much
more reactive than the other two classes. They have electron-rich double bonds (their pi
electrons are not completely delocalized, even in conjugated alkenes) that allow them to easily
undergo addition reactions.
In this experiment you will test the reactivity of the three types of hydrocarbons with
bromine, and with potassium permanganate. These are two common classification tests for
hydrocarbons. Bromine only reacts with alkanes or aromatic hydrocarbons under special
conditions.
However, bromine reacts readily, and rapidly, with alkenes to produce
dibromoalkanes. A successful reaction is indicated when the reddish-brown bromine is used
up and colorless products are formed (see below). Potassium permanganate is an oxidizing
agent that can react with alkenes to form diols, but does not react with alkanes or with aromatic
rings. It can react with alkyl substituents on aromatic rings, but only under very vigorous
conditions (high temperature etc.) A successful reaction will produce a brown precipitate
(MnO2), and the purple color of the potassium permanganate will disappear (see below).
R
C
Br
Br 2
C
R
(reddish)
R
C
(purple)
R
R
(colorless)
HO
+ 2KMnO 4 + 2CH 3OH
Br
OH
C
R
R
+ 2MnO 2 + 2KOCH 3
(brown)
MATERIALS:
Benzene / Cyclohexane, n- Hexane / cyclohexene, toluene, water, dichloromethane,
bromine solution, potassium permanganate solution, ethanol, test tubes and test tube rack
SAFETY PRECAUTIONS:
Cyclohexane, cyclohexene, toluene and ethanol are extremely flammable, do not use
near a flame. Bromine vapors can be irritating, do all bromine additions in the hood and avoid
spills. Dispose of waste in the appropriate containers. Potassium permanganate is a strong
oxidizing agent and must be disposed of in its own waste container - do not put it into the
organic waste container!!!
PROCEDURES:
1. Reactivity with Bromine:

a) Place 10 drops each of benzene / cyclohexane, n-hexane / cyclohexene and toluene in
separate clean dry test tubes, and to each add 2 drops of dilute bromine in methylene chloride.
Observe whether an immediate reaction (bromination) occurs (does the reddish color fade
away?). Note all observations.
b) If no immediate reaction occurs, place the reaction near a window (if possible) and leave it
while you do parts 2 and 3. Observe whether a slow reaction occurs and note your
observations.
2. Reactivity with Potassium Permanganate:

Dissolve 6 drops of each hydrocarbon in 2 mL of ethanol (a solvent) in separate clean dry test
tubes. Add 2 drops of 2% KMnO4 solution. Observe whether a reaction occurs (does the purple
go away and a brown precipitate form?). For a positive test, a reaction should be evident in one
minute or less. The ethanol (solvent) reacts slowly with KMnO 4, producing a brown color in
about 5 minutes (a false positive). Note all observations.
3. Solubility:
a) Place 10 drops of benzene / cyclohexane, toluene and n- Hexane / cyclohexene in three
separate, clean dry test tubes.
b) Add 20 drops of water to each test tube. Shake the test tube and note whether the
hydrocarbon dissolves. If not, note if the hydrocarbon is more or less dense than water.
c) Repeat the solubility test with dichloromethane (methylene chloride), using fresh samples of
the hydrocarbons in clean dry test tubes. Note whether the hydrocarbons dissolve in CH 2Cl2.
WASTE DISPOSAL:
Pour all solubility test solutions and bromination solutions into the organic waste
container. Pour all potassium permanganate solutions into the specially designated waste
container. Do not put potassium permanganate into the organic waste container!!
NAME: ___________________ Date: ______________________

Exercise 12
HYDROCARBONS-- STRUCTURES AND CHEMICAL PROPERTIES
Record observations about the reaction including color changes, temperature change
or any other useful information in the below table. Encircle the test reagents used:
Test:
Bromine
Benzene /
Cyclohexane
n- Hexane /
Cyclohexene
Toluene
Potassium
Permanganate
Solubility in Water
Solubility in
Dichloromethane
III. QUESTIONS
1.
How can methane, ethylene and acetylene be prepared in the laboratory?

Write the chemical reactions involved in such preparations. _______________
___________________________________________________________________
___________________________________________________________________
___________________________________________________________________
___________________________________________________________________
2.
What type of reaction is exhibited by alkenes? ___________________ Why?

___________________________________________________________________
___________________________________________________________________
___________________________________________________________________
3. Why do aromatic hydrocarbons undergo substitution reactions, rather than addition

reactions? Use chemical structures to illustrate your answer.
___________________________________________________________________
___________________________________________________________________
___________________________________________________________________
___________________________________________________________________
___________________________________________________________________
___________________________________________________________________
4. Based on their chemical structures (both shape and atomic make-up), do you expect
hydrocarbons (in general) to be more, or less, dense than water?
Explain your answer.
___________________________________________________________________
___________________________________________________________________
___________________________________________________________________
___________________________________________________________________
___________________________________________________________________
___________________________________________________________________
EXERCISE 13
SOAP
Any substance that is made from a mixture of natural oils and fats with an alkali
is considered as soap. Soap is a surface-active agent generally used for washing and
because soap is basically ineffective without water. The use of soap (or any natural
soap-cleaning agents) has always been associated with mans inherent instinct to keep
his body, his clothes, and various other washable belongings clean.
Soap making started in the 18th century by boiling a crude mixture of animal fat,
lye from wood ash, and salt until it became sticky and hard. Later, manufacturers added
certain chemicals and permissible additives to improve the quality of soap; some as
builders, other as whitening agents. Color (water soluble dyes) and fragrance are also
added to make the product, especially toilet soap, more appealing to consumers
Today, soap products are prepared in various types, shapes and sizes. Even the
ordinary laundry soap is produced now in the form of bars, cakes, flakes, liquids, gels
or pastes.
If you are interested in manufacturing soap products from detergent laundry soap
to herbal soap, you should study the technology appropriate to each type. It is also
essential that you acquaint yourself with the basic requirements to be met in soap
making. For example, an ordinary soap should be made from alkali and fats and oils
(fatty acids), a moderate amount of matter insoluble in alcohol, and permissible
additives. The finished product should neither bear any objectionable odor nor leave
objectionable odor on fabrics and dishes after washing them and rinsing thoroughly
with hot water. The soap should form suds or lather in a clean moderate hard water
(less than 180m ppm CaCO3) when tested.
There are also a prescribed standard size for bar soaps, i.e., basic size of 120
grams, with multiples in a single bar or four units in a single bar of 480 grams.
In addition to the requirements prescribed in existing laws and regulations, the
packing material of soap should be marked with the following information:
brand name of the product
quantity of individual bars contained
net mass (marked net mass is the average net mass of individual bars at time of packing)
name and address of the manufacturer
country of origin, e.g., Made in the Philippines.
This guide will introduce you to the basic procedures in making various kinds of soap.
Qualities of a Good Soap
A good soap s biodegradable when it does not contain chemicals that cannot be reverted to
their natural elements. Neither does it contain chemicals that are harmful to the environment or
cause undue destruction to the environment.
A good soap dissolves easily and removes stains from clothes, human skin or any material
being cleaned.
It dissolves in water and produces enough suds.
It gives a clear and sparkling kind of cleanliness.
It gives a pleasant smell.
A good soap does not leave sticky traces on the clothes or on the skin.
It has a color that is even and does not streak.

It disinfects or kills germs.
It does not damage the fibers of textiles.
Basic Ingredient of Soap

Fat or oil and alkali taken from lye are the basic ingredients of soap. Fat serves as the
foundation of the soap and alkali produces the chemical reaction that makes the mixture hard
and gives it cleansing ability.
Fat taken from plants like coconut, palm and cottonseed are called soft oils. Animal fat from
pigs and cows are called hard fats. Hard fats do not produce many suds, but this type of fat
solidifies and hardens easily. The soft and hard oils can be mixed to make the soap produce
more suds and solidify with the right hardness. Additives can also be mixed with the soap
ingredients. Some of these additives are coco diethanol amide (CDEA), sodium carbonate,
naptha, kerosene and rosin. Fragrances or essential oils fro lemon, patchouli, lemon grass,
citronella and rose are also usually added.
Some Important Chemical Ingredients (Additives) and their Uses

It is important to familiarized ourselves with the common chemical ingredients used and their
uses. These ingredients give the desired quality and feature of the soap. Also, the quantity of
these ingredients in making soap, dictates the cost of soap produced.
Coco Diethanol Amide (CDEA) foam or sud booster
Sodium silicate hardening and leavening agent; prevents separation or deterioration of
ingredients in liquid products
Sodium lauryl ether sulfate (SLES) cleansing agent; for thickening effect and a cheaper but
effective foamer
Sodium tripolyphosphate (STPP) a chemical that gives cleansing power
Ethylene diamine tetra acetic acid (EDTA) sequestering agent that makes the ingredients
float; used as foaming stabilizer; also used to reduce hardness in water
Caustic potash (also known as potassium hydroxide) allows bar soap to harden
Tergitol binder used for powdered detergent
Sodium phosphate provides the abrasive strength; removes hard water minerals and this
increase the effectiveness of detergents; prevents dirt from settling back into clothes during
washing
Sodium chloride or table salt thickening agent; provides viscosity to the soap
Methyl and propyl paraben anti-microbial preservatives
Triethanol amine (TEA) emulsifier used in facial cleanser
Caustic soda (also called sodium hydroxide) neutralizes or adjust the acidity of other
ingredients
Benzalkonium chloride disinfectant against bacteria, fungi and yeasts
Carboxyl methyl cellulose (CMC) anti redeposition agent that prevents dirt from settling back
into clothes during washing
Sodium sulfate provides proper flow or solubility to soap; cleans without leaving residue
Glycerin serves as moisturizer in facial cleaner
CAUTION
Commercial lye, potash lye and soda lye even dampened wood ashes are EXTREMELY
caustic and can cause burns if splashed on the skin. They could cause blindness if spattered
in the eye.
Use caution when adding lye to cold water, when stirring lye water and when pouring the liquid
soap into molds. If it is spilled on the skin, wash off immediately with cold water. Wash off any
lye or green (uncured) soap spilled on furniture or counter tops.
Though some of the old recipes didnt say so, always add lye to COLD water, never to hot
water, because the chemical action heats the cold water to the boiling point. It also produces
harsh fumes which are harmful if breathed deeply. Stand back and avert the head while the lye
is dissolving. The use of a draft vent is recommended. Because of these dangers, it is best to
keep small children from the room while soap is being made.
BASIC EQUIPMENTS NEEDED
A container A large iron soap kettle or a common wash boiler is great for making soap in
large quantities over an open fire. For indoor soap-making in smaller quantities, pots that are
granite or porcelain- covered are the best to use because of the corrosive character of some of
the recipes ingredients. Dispose of soap-making wastes carefully outdoors, not in the drain.
Never put lye or fresh soap in aluminum pans.
A Ladle If an iron kettle is used a long-handled wooden ladle is needed to stir the soap. For
indoor soap-making a wooden spoon will do. Once again dont use aluminum.
A Grater or Grinder A kitchen grater or a meat grinder is need to make soap flakes for
laundry use or to grind soap for some of the later recipes.
Molds Flat wooden boxes or wooden tubs to mold the soap while it cooled and hardened.
Laid pieces of cloth over the wood to keep the soap from sticking. You can buy fancy molds in
hobby shops, but for home use, discarded plastic bottles work just as well and are much
cheaper.
A Plate Some recipes call for a plate on which to cool a few drops of the liquid from time to
lime to test for doneness. A glass plate is preferred because it cooled the liquid faster.
Basic Steps in Soap Making:
Sufficient mixing is important in soap making. Although mixing can be done by hand, the use of
an electric stainless steel mixing tank makes work faster and gives better results.
The basic soap ingredients (fat or oil and alkali) undergo the process of saponification. Here,
the elements of the fat or oil called esters, separate and become fatty acids. Fatty acids, in
turn, get mixed with the sodium elements of the alkali and this solidifies the soap.
The soap now undergoes the cold process (the simplest technology applied in soap making).
During the cold process, fat and water are mixed thoroughly to prevent the formation of
sediments.
The soap is left to cool and harden. This is called the cooling and solidifying stage.
The bar soap is sliced and dried to remove moisture.
The sliced soap is left to age, a process which removes the effects of caustic soda.
Finally, the soap is packed for marketing and selling.

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EXERCISE 1

PROPERTIES THAT DISTINGUISH ORGANIC FROM INORGANIC

Into 3 separate test tubes, place 1 mL each of distilled water. Add a

2. Repeat the test using petroleum ether instead of water. Record

NAME: ___________________ Date: ______________________

OBSERVATIONS AND RESULTS

[Fe(SCN)6]+ 3K2SO4 + (NH4)2 SO4

Organic compound [C] [H] [O] [N] [X] [S] + N

NaCN, NaOH, NaX and

Note: X represents any of the halogens: Cl, Br and I

test tube holder

CuO & glucose

bent glass tubing

Figure 1. Set-up for Carbon and Hydrogen Test

3. Test for Halogens

b) Silver Nitrate Test

4. Test for Oxygen (Ferrox Test)

In another test tube, dissolve 3 gtts of butanol in 1 mL toluene.

5. Test for Sulfur (Lead Acetate Test)

NAME: ___________________ Date: ______________________

OBSERVATIONS AND RESULTS

(Do the test samples contain the elements tested for?)

3. Test for Halogen

5. Test for Sulfur

4. What chemical reactions are involved in the soda-lime test?

RECRYSTALLIZATION AND DECOLORIZATION

B. Decolorization of Brown Sugar

2. Heat the remaining solution to nearly boiling. Add 0.5 gram of

NAME: ___________________ Date: ______________________

OBSERVATIONS AND RESULTS

2. Crystals formed in slow cooling _______________________________

3. Solutions of purified crystals + 2 gtts of 1% AgNO3

II. A. Recrystallization of C6H5COOH ________________________________

What are the methods of inducing crystal formation from solution?

How is the completeness of separation of the C6H5COOH crystals

Evaporating dish with the mixture

Figure 2. Set-up for Sublimation Process

drops of 5% BaCl2 solution. Observe and record the result.

NAME: ___________________ Date: ______________________

RESULTS AND OBSERVATIONS

Which compound in the mixture is the sublimate? Which did not

Write the chemical reaction/s involved.

B. Test for Completeness of Separation (to be done on both distillate fractions)

NAME: ___________________ Date: ______________________

RESULTS AND OBSERVATIONS

Why is this method effective in separating acetone from water? _________

NAME: ___________________ Date: ______________________

RESULTS AND OBSERVATION

Color of extract ___________________________________________

4) What is salting-out? When is it used in the extraction process?

Intermolecular-bonding between water molecules

Intermolecular-bonding between water molecules

There are two types of hydrogen-bonding: intermolecular and intramolecular.

2) Place 4 mL of n-butyl alcohol in a dry ignition tube.

NAME: ___________________ Date: ______________________

RESULTS AND OBSERVATIONS

When are azeotropes formed? ______________________________

What are the types of intermolecular attractive forces that hold

How do these intermolecular forces affect the boiling point of a

RESULTS AND OBSERVATIONS

1. Test Compound: _______________ Structural formula _________________

3. Test Compound: _______________ Structural formula _________________

Some examples of these classes of alcohols are:

sec -butyl alcohol

NAME: _ Date: ____

NAME: _ Date: ____

NAME: _ Date: ____

NAME: _ Date: ____

NAME: _ Date: ____

NAME: _ Date: ____

NAME: _ Date: ____

1. Test Compound: _ Structural formula ___

3. Test Compound: _ Structural formula ___

NAME: _ Date: ____

NAME: _ Date: ____