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Org Chem Lab Manual
Org Chem Lab Manual
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 non-
electrolytes, 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.
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 sub-
stance left after heating.
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.
Exercise 1
PROPERTIES THAT DISTINGUISH ORGANIC FROM INORGANIC
COMPOUNDS
1. Ignition Tests
a. Flammability Ethyl alcohol
Water
b. Charring Sucrose
Sodium chloride
Calcium carbonate
Acetone in water
Naphthalene in petroleum
ether
Acetone in petroleum ether
Sodium nitrate in petroleum
ether
II. EXPLANATION OF RESULTS
1. Ignition Tests
a. Flammability
________________________________________________________________
b. Charring ___________________________________________________
2. Solubility
___________________________________________________________________________
___________________________________________________________________________
__________________________________________
EXERCISE 2
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:
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 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 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.
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.
c) 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.
Exercise 2
QUALITATIVE TEST FOR ELEMENTS IN ORGANIC COMPOUNDS
5. Sulfur
III. QUESTIONS:
1. What chemical reactions are involved in the test for carbon and hydrogen?
__________________________________________________________________________________
______________________________________________
________________________________________________________________
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.
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.
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.
PROCEDURE
A. Recrystallization of Benzoic Acid
5. Collect 5 mL of the hot filtrate in a test tube labeled “slow cooling” and
set it aside to cool slowly.
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.
3. Transfer 2 mL of the filtrate in a test tube. Compare its color with that
of the control.
NAME: ___________________ Date: ______________________
Group No. ________________ Class Schedule: _____________
Exercise 3
Separation and Purification of Compounds
RECRYSTALLIZATION AND DECOLORIZATION
1. Description of mixture:
a. Before heating ____________________________________________
___________________________________________________________
b. After heating _____________________________________________
___________________________________________________________
c. After filtration_____________________________________________
___________________________________________________________
III.QUESTIONS
1. How was the colored impurities removed from the mixture? ________
___________________________________________________________
___________________________________________________________
4. What are the factors that causes the differences in sizes of the
crystals formed? ____________________________________________
___________________________________________________________
___________________________________________________________
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.
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
Hot plate
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.
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.
Exercise 4
Separation and Purification of Compounds
SUBLIMATION
1. Description of mixture:
a. Before heating ____________________________________________
___________________________________________________________
b. While heating _____________________________________________
___________________________________________________________
c. Upon cooling:
sublimate _______________________________________________
___________________________________________________________
___________________________________________________________
residue _________________________________________________
___________________________________________________________
___________________________________________________________
II. QUESTIONS
1. What properties do substances which undergo sublimation process?
__________________________________________________________
___________________________________________________________
___________________________________________________________
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.
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 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.
PROCEDURE:
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: ______________________
Group No. ________________ Class Schedule: _____________
Exercise 5
Separation and Purification of Compounds
DISTILLATION
Procedure A
1. 56 °C
Procedure B
Sample quantity
used:
___________
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
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.
APPARATUS/MATERIALS: REAGENTS:
PROCEDURE:
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.
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: ______________________
Group No. ________________ Class Schedule: _____________
Exercise 6
Separation and Purification of Compounds
EXTRACTION OF CHLOROPHYLL
III. QUESTIONS
1) What are the indications that the desired substances have been extracted?
___________________________________________________________________
___________________________________________________________________
_________________________
EXERCISE 7
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 H
:
O O
H H H H
H
R-O–H
O H
O H
H H O
H
Intermolecular-bonding between water 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 molecule’s
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.
Exercise 7
BOILING POINT
Structural formula:
Name:
Structural formula:
Name:
Structural formula:
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?
___________________________________________________________________
___________________________________________________
EXERCISE 8
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 1º 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.
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 1º to 2º 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.
Exercise 8
MELTING POINT
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?
_______________________________________________________
_______________________________________________________
_______________________________________________________
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.
R R R
l ZnCl2 l l
R – C –OH + HCl R–C+ R – C – Cl + H 2O
l l l
R R R
CH2OH CH2OH
l l
CH2OH CHOH
l
CH2OH
Ethylene glycol glycerol
1, 2- ethanediol 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 H–C=O
l l
CHOH + KHSO4 CH + 2H2O
l l
CH2OH CH2
REAGENTS
PROCEDURE
2. LUCAS TEST
a. Into 4 separate test tubes, place drops each of the following: tert-butyl alcohol, sec-butyl
alcohol, n-butyl alcohol, and benzyl alcohol.
b. To each test tube, add 20 drops of freshly prepared Lucas reagent. Shake only once and
let it stand.
c. 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. 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.
b. Note the odor and the time required for the odor to develop.
5. IODOFORM TEST
a. To 4 drops of ethyl alcohol, add 4 ml of iodine solution. Then add drop by drop 10%
NaOH until the iodine is decolorized.
b. Place the test tube in a warmth bath (60°C). Note the odor of the vapors and the color of
the precipitate formed.
c. Repeat the test with: 1) isopropyl alcohol, 2) methyl alcohol, in place of ethyl alcohol.
7. FERMENTATION
a. Slice the overripe fruit (peel already removed) into chunks and osterized in an electric
blender.
b. Pass the puree into cheesecloth.
c. Measure the volume of the juice and add 5 grams of Baker’s yeast for every 500ml of the
juice. Mix thoroughly.
d. Place the mixture in a 1 Liter Erlenmeyer flask. Cover with one-holed rubber stopper with
a U-shaped glass tubing.
e. Dip the other end of the glass tubing in 50 ml lime water and set aside the set-up for 5
days.
Cork
Exercise 9
ALCOHOLS
Name of Test
Compounds Reagents RESULTS
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
4. Special Test for
Methanol
5. IODOFORM TEST
ethyl alcohol ________________________
_
isopropyl alcohol ________________________
methyl alcohol _
________________________
_
6. ACROLEIN TEST
glycerol
7. FERMENTATION
Flammability test
Chromic acid 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.
____________________________________________________________________________
____________________________________________________________________________
4. Give one important commercial method of preparing ethyl alcohol in the Philippines.
Write chemical reaction involved.
____________________________________________________________________________
____________________________________________________________________________
____________________________________________________________________________
____________________________________________________________________________
____________________________________________________________________________
Exercise 10
SYNTHESIS OF ETHYL ALCOHOL
Solubilities
Ether
Acetone
Chloroform
Distilled water
Chemical test
Combustion test
Lucas test
Calculation/s
Question/s:
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.
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.
REAGENTS
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. MILLON’S TEST
Into 2 separate test tubes, place 1 nl of each of 1% phenol and 5% albumin. Add 6
drops of Millon’s reagent. Shake. Boil in a water bath. Note the color produced.
Exercise 11
PHENOL
4. Phenolphthalein formation
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5. Million’s Test
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III. QUESTIONS
1. Explain why Br replaces H’s at the 2,4, 6 positions in its reaction with phenol.
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2. Write the reaction involved in the formation of phenolphthalein. Identify the functional
group in phenolphthalein, which is responsible for the indicator property?
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EXERCISE 12
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 can’t 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 R Br Br
C C + Br 2 R C C R
R R R R
(reddish) (colorless)
R R HO OH
C C + 2KMnO 4 + 2CH 3OH R C C R + 2MnO 2 + 2KOCH 3
R R R R
(purple) (brown)
MATERIALS:
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:
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.
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:
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: ______________________
Group No. ________________ Class Schedule: _____________
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:
Bromine
Potassium
Permanganate
Solubility in Water
Solubility in
Dichloromethane
III. QUESTIONS
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.
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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 man’s 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.
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 didn’t 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 – don’t 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.