CHEM 31 - Laboratory Manual

1
Experiment No. 1
SOME DIFFERENCES IN PROPERTIES BETWEEN ORGANIC AND
INORGANIC COMPOUNDS
Name: ___________________________________
______________
Teacher's signature: ________________________
Date:
I. PRE-LAB:
Cite three significance of organic chemistry to everyday lives
1.
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2.
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3.
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II. OBJECTIVE:
To study some common differences in properties between organic and
inorganic compounds
III. APPARATUS:
Bunsen burner
Watch glass
Crucible tong
Vials
Vial brush
IV. MATERIALS:
Drops of the following:
0.1 M potassium permanganate
6 M sulfuric acid
0.1 M iron (II) sulfate
Coconut oil
Kerosene
Denatured alcohol
Pinch of the following:

Table salt
Sugar
Sand
Starch
Piece of:
Aluminum foil
Wax
Leaf
Plastic
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V. PROCEDURE
1. Composition
On a piece of
broken crucible, heat strongly each of the following:

pinch of sugar
pinch of sand
piece of plastic
piece of aluminum foil
pinch of starch
piece of leaf
Write observations and classify each substance as to organic or inorganic

substance.
Observation
Organic / Inorganic
Sugar
Sand
Plastic
Aluminum
foil
Starch
Leaf
What element is common to all organic compounds? _______________.

2. Combustibility
Ignite a small piece of wax placed on a broken crucible. Observe. Repeat with
grains of table salt.
Write observations and classify each substance as to organic or inorganic
substance.
Observation
Organic / Inorganic
Wax
Table salt
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Observation
Organic / Inorganic
Explanation:
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3. Solubility
Place in separate vials, 3 drops of coconut oil and grains of table salt. To each
vial, add 10 drops of water. Shake. Observe.
Repeat the above procedure using kerosene instead of water. Observe. Write
observations and classify each substance as to organic and inorganic
substances.
Water
Kerosene
Organic / Inorganic
Coconut Oil
Table salt
Explanation:
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4. Rates of Reaction
Place 5 drops of freshly prepared 0.1 M FeSO4 in a clean vial. Add 2 drops of 6
M H2SO4 and 2 drops of 0.1 M KMnO4. Note the time it takes for the color of
KMnO4 to disappear.
Repeat the above procedure using denatured alcohol instead of FeSO4. Again,
note the time it takes for the color of KMnO4 to disappear.
Compare the rates of the two reactions. Write observations and classify each
substance as organic or inorganic.
Time
Organic / Inorganic
FeSO4 + H2SO4 + KMnO4

Den. alcohol + H2SO4 +
KMnO4
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Explanation:
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POST-LAB:
Summarize the differences between properties of organic and inorganic
compounds. Tabulate your answers.
Experiment No. 2
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COMPOSITION OF MOST ORGANIC COMPOUNDS

Name: ___________________________________
______________
Teacher's signature: ________________________
Date:
I. PRE-LAB:
Define Organic Chemistry
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Give three reasons why carbon can form many different compounds.
1.
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2.
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3.
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II. OBJECTIVE:
To test for the presence of elements common to most organic
compounds
III. APPARATUS:
Bunsen burner
Vials
Copper wire
IV. MATERIALS:
Drops of:
conc. Lead acetate, conc.
10 mL 1M sodium hydroxide
1 ml conc. Sulfuric acid
Litmus paper
Dry egg albumin
Chem 31.1
Ammonium molybdate
1 mL conc. Nitric acid
Chloroform
Milk
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V. PROCEDURE:
Carbon, hydrogen and oxygen with small amount of halogens, nitrogen,
sulfur and phosphorous are the chief elements found in organic compounds.
A. Carbon and Hydrogen
Organic compounds are frequently inflammable and when heated take fire
or char.
Heat a small amount of egg albumin in a vial.
Observations.
What collects in the upper and cooler portion of the test tube?
__________________________
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Continue heating until there is no further change. The charring indicates the
presence of _______ while the formation of water indicates the presence of
_________________________.
B. Nitrogen
Organic compounds containing nitrogen evolve ammonia when heated with
soda lime.
Mix a small amount of dry egg albumin with equal amount of soda lime. Heat
the mixture in a dry vial. Observe the odor of the gas evolved. Hold a piece
of red litmus paper at the mouth of the tube.
Observations.
What gas was evolved that turned the moistened red litmus paper to blue?
________________.
C. Sulfur
Loosely bound sulfur in organic compounds forms sodium sulfide when
boiled with sodium hydroxide.
Add a small pinch of egg albumin to a vial containing 20 drops of NaOH and
boil. Cool the vial in running water and add a few drops of lead acetate.
Observations.
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Repeat the above procedure using few strands of hair instead of egg
albumin.
What is the color of the precipitate? _____________________
Give the name and formula of the precipitate.
Equation.
D. Phosphorus
On oxidation, phosphorous change to phosphate, which forms yellow
precipitate with ammonium molybdate.
To 5 drops of milk in a vial add 5 drops of conc. Nitric acid and 5 drops of
conc. Sulfuric acid. Boil in a water bath for 5 minutes. Cool the vial and dilute
the solution with equal volumes of water. Add few drops of conc. Ammonium
molybdate and warm. Observe the color of the precipitate formed.
Observations.
_______________________________ precipitate indicates the presence of
phosphorous.
Equation.
E. Halogens
Heat the loop of the copper wire over the flame for 5 minutes or until it does
not give any color to the flame. Allow to cool. Dip the the heated copper
wire into a watch glass containing chloroform. Bring the end of the copper
wire to the outer region of a nonluminous flame and observe the color of the
flame immediately.
What is the color of the flame? ____________________________________________
What is responsible for the color of the flame? _______________________________
What is the name of this test? _____________________________________________
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POST-LAB:
1. What element/s is/are common to organic compounds?
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2. Why is it more difficult to test the presence of chlorine in organic
compounds than in inorganic compounds?
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3. When a piece of hard-boiled egg is left in contact with a silver spoon, a
black spot formed on the spoon. Explain.
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Experiment No. 3
PURIFICATION OF ORGANIC COMPOUNDS
Name: ______________________________________
Teachers Signature: ___________________________
Date: _____________
I. PRE-LAB:
1. What is crystal and what is meant by recrystallization?
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2. How does recrystallization free a substance from impurities? Explain how
each step in recrystallization contributes to the removal of impurities?
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3. What is sublimation?
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II. OBJECTIVE:
To demonstrate the different processes involved in the purification of
organic compounds
III. APPARATUS:
Bunsen burner
Beakers
Filter paper
Evaporating dish
Separatory funnel
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Clay flame shield

Buchner funnel
Erlenmeyer flask
Watch glass
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IV. MATERIALS:
Impure Acetanilide (90 % acetanilide + 10 % NaCl and trace of red
dye)
Activated charcoal
Benzoic acid
Chloroform
dil. Nitric acid
Ice
Distilled water
Sodium chloride
Silver nitrate
V. PROCEDURE:
A. Purification of Solids by Recrystallization
The products of chemical reactions can be impure. Purification of
products must be performed to remove by-products and impurities. Liquids
are customarily purified by distillation, while solids are purified by
recrystallization (sometimes called simply "crystallization").
Recrystallization is a method of purifying a solid. There are two types
of impurities: those more soluble in a given solvent than the main
component and those less soluble. (If there are any impurities that have the
same solubility as the main component, then a different solvent needs to be
chosen.)
Recrystallization relies on the different solubilities of solutes in a
solvent. Compounds, which are less soluble, will crystallize first. The
crystallization process itself helps in the purification because as the crystals
form, they select the correct molecules, which fit into the crystal lattice and
ignore the wrong molecules. This is of course not a perfect process, but it
does increase the purity of the final product.
The solubility of the compound in the solvent used for recrystallization
is important. In the ideal case, the solvent would completely dissolve the
compound to be purified at high temperature, usually the boiling point of the
solvent, and the compound would be completely insoluble in that solvent at
room temperature or at 0oC. In addition the impurity either would be
completely insoluble in the particular solvent at the high temperature, or
would be very soluble in the solvent at low temperature. In the former case,
the impurity could be filtered off at high temperature, while in the latter case
the impurity would completely stay in solution upon cooling. In the real
world, this will never happen and recrystallization is a technique that has to
be practiced and perfected.
Regardless of crystallization method, the purity of the solid can be
verified by taking the melting point.
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A good (suitable) recrystallization solvent will dissolve a large amount

of the impure compound at temperatures near the boiling point of the
solvent. Small amount of compound being purified should remain in solution
at low temperatures, between approximately 25 and 5 oC. Low solubility at
low temperatures minimizes the amount of purified compound that will lose
during recrystallization.
A suitable recrystallization solvent should also be partially volatile in
order to be easily removed from the purified crystals. The solvent should not
react with the compound being purified and it should have the boiling point
below the melting point of the compound being purified because solid melts
before dissolves (oiling out). In selecting a good recrystallization solvent one
should also consider flammability, toxicity, and expense.
In selecting a solvent consider that like likes like. Polar compounds
dissolve polar compounds and non-polar compounds dissolve non-polar
compounds. The most commonly used recrystallization solvents are
presented in Table 3.1.
Table 3.1 Recyrstallization solvents
Solvent
Formula
polarity
Boiling point
(0C)
water
H 2O
very polar
100
ethanol
CH3CH2OH
polar
78
methanol
CH3OH
polar
65
dichlorometha
ne
CH2Cl2
slightly
polar
40
diethyl ether
(CH3CH2)2O
slightly
polar
35
Organic compounds with one polar functional group and a low number
of carbon atoms such as methanol, ethanol, and n-propanol are highly
soluble (miscible) in water. These alcohols form hydrogen bond with water
due to the polar OH functional group. As the number of carbons per polar
functional group increase, solubility decreases. The solubility of alcohols with
four to five carbons is in Table 3.2.
Table 3.2. Solubility of Alcohols
Alcohol
Formula
Solubility (g/100 ml
H2O)
n-butanol
CH3CH2CH2CH2OH
npentanol
CH3CH2CH2CH2CH2OH
n-hexanol
CH3CH2CH2CH2CH2CH2OH
0.5
CH3CH2CH2CH2CH2CH2CH2OH
0.1
nChem 31.1
pentanol
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Compounds with six or more carbons for each polar group will not be
very soluble in polar solvents but will be soluble in non-polar solvents such
as benzene and cyclohexane. If a single solvent cannot be found that is
suitable for recrystallization, a solvent pair often used. The solvents must be
miscible in one another. Some commonly used solvent pairs are waterethanol, acetic acid water, ether-acetone. Typically, the compound being
recrystallized will be more soluble in one solvent than the other. The
compound is dissolved in a minimum amount of the hot solvent in which it is
more soluble. (Source: Dr. Pahlavan. Recrystallization of Benzoic Acid)
The following formulas used in solubility problems.
% lost in cold solvent = (solubility in cold solvent/solubility in
hot solvent) x100
% recovery of solid = [g (solid) g (solid lost)] x 100 / g
(solid)
Example: The solubility of solid X in hot water (5.50 g/100 ml at 100 oC) is
not very great, and its solubility in cold water (0.53 g/100ml at 0 oC) is
significant. What would be the maximum theoretical percent recovery from
crystallization of 5.00 g of solid X from 100 ml water? Assuming the
solution is chilled at 0 oC.
Percent solid lost in cold water
= (solubility in cold water/ solubility in
hot water) x100
= (0.53/5.50) x100 = 9.64%
grams solid lost in cold water
lost
= grams mass of original solid x percent

= 5.00 g x 9.64% = 0.482 g
g (solid recovered)
= g (solid) g (solid lost)

= 5.00 0.482 = 4.52 g
% recovery
= g (solid recovered) x100 / g (solid)

= (4.52/5.00) x100 = 90.4 %
Place 5 grams of impure acetanilide (90 % acetanilide + 10 % NaCl and trace

of red dye) and 150 mL of tap water in a beaker. Heat the contents and stir
constantly. When the acetanilide dissolves, add 1 gram of activated charcoal
and continue heating. Boil the solution, then filter. If the filtrate is not
colorless, repeat the process by adding more charcoal. Collect equal
amounts of the filtrate in two separate containers. Cover one container with
a watch glass and set aside to cool slowly. Place the other container in ice
water and stir while cooling. When crystallization is completed in both
containers, compare the size of the crystals.
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Observations.
Filter both crystals using a Buchner funnel for suction filtration. All crystals
must be on the filter paper. Remove the filter paper and place it on a watch
glass, and allow to dry overnight. When completely dry, weight the crystals.
Calculate the percentage yield of purified crystals using the formula.
% yield =
Actual yield
Theoretical yield
100
Questions:
1. What is mother liquor?
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2. Why must the filtration be carried out quickly?

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3. What must be considered in choosing a solvent for recrystallization?
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4. What is the relationship between the rate of cooling and size of crystals?
Explain.
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5. What is the relation of surface contamination and occluded materials to
small and large crystals? Explain.
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6. Give some reasons why suction filtration (vacuum) is to be preferred to
gravity filtration.
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B. Liquid-Liquid Extraction
Place 1 gram of benzoic acid contaminated with sodium chloride in a beaker.
Dissolve the mixture in 100 mL of tap water by heating. Cool to room
temperature and pour the solution into a separatory funnel. Add 3 mL of
chloroform. Stopper and shake thoroughly. Allow the two liquids to separate
into distinct layers. Then withdraw the chloroform layer into an evaporating
dish. Repeat the extraction with 3 mL of chloroform. Combine the chloroform
extracts. Reserve the upper layer for the next operation. Evaporate slowly
the chloroform extracts on a water bath.
Compare the residue with the original mixture.
% yield benzoic acid
Test for Chlorides:

To 5-10 mL of the upper layer, add a drop of dilute nitric acid and 1 drop of
silver nitrate
Observation.
Equation.
Questions:
1. Give the name and formula of the residue obtained in the experiment
__________________
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2. What is meant by saying the two liquids are immiscible?

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3. Could alcohol be substituted for chloroform in the above process? Why/
Why not?
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4. Why is it necessary to remove the stopper from a separatory funnel when
liquid is being drained from it through a stopcock?
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C. Purification of Solids by Sublimation
Place 1 gram of impure benzoic acid contaminated with sodium chloride in a
clean and dry 400 mL beaker. Then cover it by placing a Florence or
Erlenmeyer flask half filled with tap water. Heat very slowly with a small
flame. Cool the beaker. Remove the flask carefully when the setup is cool.
Scrape the crystals clinging to the flask and collect them on a previously
weighed paper. Get the weight of the crystals.
Observations.
% yield:
POST-LAB:
1. What limitations are encountered in the application of sublimation as a
general method of purification?
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2. You want to purify 10 g of Compound A that has been contaminated with 0.2 g of
Compound B. Solubilities in water of the two compounds are given in the following
table.
Solubility at
Solubility at
20 C (g/10 mL)
100C (g/10 mL)
Compound A
0.029
0.680
Compound B
0.22
6.67
Compound
1. What volume of boiling water is needed to dissolve the 10 g of Compound A?

2. How much Compound A will crystallize after cooling to 20C?
3. Will any Compound B crystals also form?
4. What is the maximum amount of Compound A that can be recovered in the
first crop of this recrystallization?
5. Will the Compound A be pure?
3. Combustion analysis of caffeine gives the following composition: 49.68 %

carbon, 5.04 % hydrogen, 16.27 % oxygen, 29.01% nitrogen. Calculate the
empirical formula of caffeine. Molecular weight determination gave 197. Find
the molecular formula. Show your solution.
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Experiment No. 4
SIMPLE DISTILLATION
Name: ______________________________________
Date: _____________
PRE-LAB:
1. What is distillation? What two processes are involved in the distillation
process?
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2. What kind of material can be separated by means of distillation? Give two
examples.
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Examples: a. __________________________
b. __________________________
II. OBJECTIVES:
After completing this activity, you should be able to:
1. Assemble a distillation setup properly
2. Name the parts of the distillation setup
3. Give the function of each part in the distillation setup
4. Give the importance of distillation process
5. Perform distillation
III. APPARATUS:
1 Distilling flask
2 iron stand and ring
3 clamps
1 burner
1 watch glass
Corks
1 Thermometer
1 Wire gauze
1 adapter
1 funnel
Boiling chips
Condenser
IV. MATERIALS:
Potassium permanganate
50 % alcoholic solution
V. PROCEDURE:
1. Set-up a simple distillation apparatus. Have the set-up approved by the
instructor.
2. Pour 120 mL of an alcoholic solution into the distilling flask. Add boiling
chips or clay chips inside the flask. Distill the liquid slowly at a uniform rate,
generally between 30-60 drops per minute. Adjust the size of the flame, if
necessary, to maintain gentle boiling. Use a watch glass as a receiver.
Record the thermometer reading when the first drop of the distillate falls and
after 2 mL of the distillate is collected. Draw out this first two mL distillate
and continue the distillation process using a new receiver (test tube). Quickly
check the flammability of the fresh distillate collected by applying a lighted
matchstick on the watch glass. Record the length of time it burns. Note any
residue on the watch glass. Repeat the test with the last two mL of the
distillate after collecting about 20 mL of the distillate.
Observations.
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Questions.
Based on the results of your test for combustion, which fraction has the
higher ethanol content? Why? Explain the difference in results.
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Has an effective separation been attained? Support your answer.
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3. Pour 100 mL of a colored solution into the distilling flask and distill. Note
the thermometer reading when the first drop of distillate falls into the
receiver. Record the thermometer reading after every five minutes until 20
mL of distillate has been collected. Return the residue to the receptacle
provided.
Observations.
Question:
Has an effective separation been attained? Support your answer.
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POST-LAB:
1. If the water inlet and water outlet are interconverted in the distillation
setup, will the distillation be still effective? Why?
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2. In the set-up, where would the mercury bulb of the thermometer be? Why?
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3. Should a distilling flask at the beginning of the distillation be filled to not
more than 2/3 its capacity and not to less than 1/3 its capacity? Why?
______________________________________________________________________________
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4. Why is it dangerous to heat a compound in a distilling flask assembly that
is closed tightly at every joint and has no vent nor opening to the
atmosphere?
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5. What is the use of boiling chips in a distillation setup? Give one reason
why we cannot reuse boiling chips?
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6. Draw the simple distillation setup and give the function of each part.
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Experiment No. 5
STEAM DISTILLATION OF ESSENTIAL OILS
Name: ______________________________________
Date: _____________
I. PRE-LAB:
1. What is steam distillation?
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2. What characteristics must a substance possess for it to be separated from
a heterogeneous mixture by steam distillation?
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II. OBJECTIVES:
After completing this activity, you should be able to:
1. Assemble a steam distillation set-up
2. Learn the function of all its parts
3. Compare steam distillation with simple distillation as a separation
method
4. Use steam distillation in the separation of slightly volatile
substances from those which are nonvolatile
5. Isolate essential oils from fresh plant material
III. APPARATUS:
1 Distilling flask
2 iron stand and ring
3 clamps
2 burners
Condenser
Corks
Safety tube
Platform balance
Dropper vial
1 Thermometer
2 Wire gauze
1 adapter
1 funnel
Boiling chips
Steam generator
Round bottom flask
Separatory funnel
IV. MATERIAL:
To be brought by students: 250 g essential oil source
V. PROCEDURE:
A. STEAM DISTILLATION
(Refer to the figure on steam distillation)
1. Add enough distilled water to the steam generator so that it is half-full.
2. Fit a safety tube into the steam generator.
3. Cut the plant material into small pieces and get the weight. Place the plant
sample inside the distilling flask up to two-thirds full. Record the weight of
the plant sample used for steam distillation.
4. Mix the sample with enough distilled water in the distilling flask.
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5. Assemble the rest of the setup. Check all connections for tightness. Show
your setup to your instructor for inspection before starting the experiment.
6. Heat the steam generator with a strong flame. Heat the sample flask with
a low flame.
7. Collect about 200 mL distillate into a 250 mL separatory funnel.
Observations.
B. SEPARATION OF THE ESSENTIAL OIL FROM THE STEAM DISTILLATE
1. Allow the organic and aqueous layers to separate in the separatory funnel.
If the separation is not clear, add a pinch of sodium chloride. Shake. Let it
stand.
2. Drain the aqueous layer slowly out of the separatory funnel.
3. Transfer the remaining oily layer into a previously weighed clean vial using
a dry dropper.
4. Determine the weight of the oil and calculate the percentage yield.
Observations.
Label the vial properly, indicating the source, lab section and date. Submit to
your instructor.
% yield =
actual yield
Theoretical yield
x 100 %
POST-LAB:
1. Explain the role of steam in facilitating the distillation of essential oil.
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2. Compare and contrast simple from steam distillation in terms of type of
mixture separated and principle involved.
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______________________________________________________________________________
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3. How may the addition of salt such as sodium chloride facilitate the
separation of the immiscible layers?
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
4. Draw the steam distillation setup. Give the function of each part in the
setup.
Experiment No. 6
MELTING POINT DETERMINATION
Name: ______________________________________
Date: _____________
The melting point of a compound is the temperature at which it

changes from solid to liquid phase. Experimentally, melting point is actually
recorded as the range of temperatures in which the first crystal starts to
melt until the temperature at which the last crystal just disappears.
Reasons for determining melting points:
1. The melting point indicates the level of purity of a sample.
The presence of an impurity in a sample will both lower the
observed melting point, and cause melting to occur over a broader
range of temperatures. Generally, a melting temperature range of
0.51.0 C is indicative of a relatively high level of purity. It follows
that for a material whose identity is known an estimate of the
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degree of purity can be made by comparing melting characteristics

with those of a pure sample.
2. The melting point helps to identify unknown samples, narrowing the
number of possibilities, because a pure solid melts reproducibly
over a narrow range of temperatures.
3. The melting point helps to characterize and identify new
compounds.
I. PRE-LAB:
1. Define the following terms:
1 a. melting point
1 b. sublimation
1 c. sintering
1 d. eutectic mixture
2. What is the effect of a small amount of impurity on the melting point of an
organic compound?
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______________________________________________________________________________
II. OBJECTIVE:
1. To determine and compare the melting points of benzoic acid and
benzoic acid-urea mixture
2. To determine the melting point of an unknown solid sample
III. APPARATUS:
Capillary tubes
Beaker with oil
2 pc. Rubber band
Thermometer
Stirring rod
IV. MATERIALS:
Benzoic acid
Benzoic acid-urea mixture
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V. PROCEDURE
Filling of Melting Point Capillaries
1. Prepare two capillaries (1 mm in diameter and 6 cm in length). Seal one
end of each capillary.
2. Grind a small pinch of pure benzoic acid to a fine powder using mortar and
pestle being careful not to contaminate the sample. Introduce the powdered
sample into the capillary tube until it occupied about 2-3mm in height. Push
the open end of the capillary into the powder and tap the closed end on the
table top.
3. Obtain another pinch of benzoic acid and add a pinch of urea. Powder the
mixture using mortar and pestle, and then introduce to the second capillary
tube. Attach the two capillaries to the thermometer as shown in Figure 1.
Determination of Melting Point
1. Fill a dry beaker about 2/3 full with coconut oil and rest the beaker on top
of a wire gauze on an iron ring.
2. Support the thermometer firmly from a ring stand by means of a clamp so
that the mercury bulb is dipped near the bottom of the beaker (about 1 cm
from the bottom). Have the setup approved by the instructor. See Figure 6.1.
3. The rate of heating should be such as to cause rise on temperature of
about 1 0C per minute and the oil bath must be stirred continuously. The
temperature at which the sample starts to melt and that at which it is
entirely liquid are noted. For a pure sample, this whole process may occur
over a range of only 0.5-1.0 0C. These values are recorded as the melting
point range.
It is often time-saving to run a preliminary melting point determination,
raising the temperature of the bath very rapidly. After the approximate
melting point determination, is known, a second determination is carried out
by raising the temperature rapidly until with 5 degrees of the approximate
value and then proceeding slowly as described. A fresh sample of the
substance should always be used for each determination.
Chem 31.1
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27
Figure 6.1. Melting Point Apparatus
Observations.
Table 6.1. Melting points of pure benzoic acid and benzoic acid-urea mixture
Theoretical MP range
Experimental MP range
Benzoic acid
Benzoic acid-urea
mixture
Question:
Compare the observed melting points of benzoic acid and benzoic acid-urea
mixture.
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
Determine the melting point range of an unknown solid given by your

instructor. Refer to Table 6.2.
Table 6.2. Melting point data for the possible unknown samples.
Substance
Acetanilide
Chem 31.1
Melting Point (oC)

113.5-114.0
UP Cebu
28
Benzoic acid
Benzamide
Adipic acid
Salicylic acid
Succinic acid
Urea
Oxalic acid
Acetamide
Aspirin
121.5-122
128.0-130.0
152.0-154.0
158.5-159
184.5-185.0
132.0-134.0
189.0-191.0
78.0-80.0
138.0-140.0
Unknown no.
______________________
Melting point range of unknown:
______________________
Identity of unknown:
______________________
POST-LAB:
1. Why should a solid be finely divided powdered for use in a melting point
determination?
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
2. Why should the oil bath should be continuously stirred during the
determination.
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
3. You and your lab partner take melting points of the same sample. You observe
a melting point of 98-104C, while your partner observes a value of 107-109C.
Explain how you can get two different values with exactly the same sample.
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
4. For a pure compound, what can a high melting point or low melting point
indicate about its intermolecular forces of attraction?
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
Chem 31.1
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29
Experiment No. 7
BOILING POINT DETERMINATION
Name: ______________________________________
Date: _____________
The boiling point of a compound is the temperature at which it

changes from a liquid to a gas. Boiling point is the temperature at which the
vapor pressure of the liquid exactly equals the pressure exerted on it,
causing the liquid to "boil" or change to the gas phase.
The molecules of compounds that exist in the liquid state are relatively
close together, compared with molecules of gaseous compounds. The close
proximity of molecules in the liquid state allow these molecules to interact
via non-covalent interactions (dipole-dipole, H-bonding, van der Waals
forces). In general, these interactions are favorable and help to hold the
molecules together in a defined volume, but still allow free motion or "flow".
Conversely, molecules of a gaseous compound are much farther away from
each other and are not confined to a specific volume by non-covalent
interactions. If enough energy (often in the form of heat) is provided to the
Chem 31.1
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30
liquid, the molecules begin to move away from each other by "breaking" the
non-covalent forces that hold the compound in the liquid state.
Structural features of a compound influence the boiling point by
increasing or decreasing the molecules' ability to establish and maintain
non-covalent interactions that hold the molecules close together in the liquid
state. The structural features of a compound that influence boiling point are:
(a) Polarity - Increased H-bonds, polar covalent bonds or formal charges in a
molecule tend to increase the boiling point. More polar elements in a
molecule increase the total number of dipole-dipole, ion-dipole and/or Hbonding interactions. More energy (higher boiling point temperature) is
necessary to break these interactions and allow the molecules to move away
from each other into a gaseous state.
(b) Molecular Weight - Increased molecular weight increases boiling point. A
higher molecular weight compound has more atoms that can be involved in
non-covalent interactions. The greater the number of non-covalent
interactions, the more energy (higher boiling point temperature) that is
necessary to break the non-covalent interactions to transform the compound
from the liquid phase to the gas phase.
(c) Branching - Branching decreases boiling point. It blocks molecules from
packing together too closely. The closer molecules are, the stronger the noncovalent interactions. Thus, molecules that are forced to be farther away
from each other due to branching have weaker non-covalent interactions.
Less energy (lower temperatures) is needed to induce a phase change from
the liquid phase to the gas for branched compounds relative to straight
chain compounds.
(Source: Cailao, Ma. Victoria T. and Masigan, Maureen Margaret R., 2009)
I. PRE-LAB:
What is boiling point? Why can it be used as an index of purity?
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
II. OBJECTIVE:
1. To determine the boiling point of distilled water
2. To determine the boiling point of unknown compounds
3. To correlate this physical constant to the molecular structure of the
compound
Chem 31.1
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31
III. APPARATUS:
Capillary tubes
Beaker with oil
2 pc. Rubber band
Burner
Thermometer
Stirring rod
Iron ring and stand
IV. MATERIALS:
Distilled water
Unknown liquid sample
V. PROCEDURE
1. Place 1-2mL of distilled water in a vial.
2. The capillary tube was introduced into the vial with the open end
immersed in the liquid sample.
3. Attach the vial to thermometer with a rubber band so that the liquid is
alongside the thermometer bulb, and place the assembly into a clear oil
bath. See Figure 7.1.
4. Heat the bath gradually until a rapid stream of bubbles emerges from the
inverted capillary and stir continuously. Remove the flame and allow the bath
to cool while stirring.
5. Record the temperature when bubbling ceases and allow the liquid to rise
in the capillary.
6. After the liquid has risen, heat the oil bath slowly, until the first bubble
comes from the capillary and record the temperature when this happens. The
two temperatures approximate the boiling range of the liquid.
The temperature at which the bubbling ceases and the liquid just begins
to rise in the capillary is recorded as the boiling point of the liquid.
7. Perform two trials.
8. Record the barometric pressure.
9. Repeat the same procedure using the unknown provided by the instructor.
Refer to Table 7.1.
Chem 31.1
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Figure 7.1: Boiling Point Apparatus
Observations.
Melting Point range of water:

Trial 1: _________________
Trial 2: _________________
Table 7.1. Boiling point data for the possible unknown samples.
Substance
Cyclohexane
Ethyl acetate
Amyl acetate
Methyl alcohol
Benzonitrile
Benzaldehyde
Ethyl alcohol
Isopropyl alcohol
Aniline
Acetone
Unknown no.
Chem 31.1
Melting Point (oC)

81
77
149
65
190.7
178.1
78.37
82.5
184.1
56
______________________
UP Cebu
33
Boiling point range of unknown:
______________________
Identity of unknown:
______________________
Notes:
If a piece of dark paper or other suitable material is placed behind the oil bath, it is
easier to see the bubbles coming from the capillary tube.
As the liquid was being heated the air expanded in the inverted capillary. The liquid
was actually superheated when rapid bubbles emerged from the capillary but on
cooling the point was reached at which the pressure inside the capillary matched
the outside pressure. This is by definition, the boiling point.
POST-LAB:
1. Which has a higher boiling point, hexane or pentanol? Why?
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
2. What effect (increase, decrease, no effect) would each of the following
have on the observed boiling point range of the sample? Why?
a. Rapid heating
________________________________________________________________________
________________________________________________________________________
b. Poor circulation of the bath liquid
________________________________________________________________________
________________________________________________________________________
c. Use of so much sample which extends considerably beyond the
thermometer
________________________________________________________________________
________________________________________________________________________
3. Will the boiling point of a liquid sample, increase or decrease when
contaminated with:
a. Volatile impurity? Why?
Chem 31.1
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________________________________________________________________________
________________________________________________________________________
________________________________________________________________________
b. Nonvolatile impurity? Why?
________________________________________________________________________
________________________________________________________________________
________________________________________________________________________
Experiment No. 8
ALIPHATIC HYDROCARBONS
Name: ______________________________________
Date: _____________
I. PRE-LAB:
1. Draw structures of the following compounds.
a. 2,7-dimethyloctane
b. 2,3-dimethyl-2-butene
Chem 31.1
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35
c. 1,6-heptadiene
d. cis-3-octene
2. Classify the compounds above as saturated or unsaturated hydrocarbon.
II. OBJECTIVE:
To study some common properties of aliphatic hydrocarbons
III. APPARATUS:
Acetylene generator
Vials
Vial corks
Watch glass
Test tube holder
IV. MATERIALS:
Drops of cyclohexane
1% potassium permanganate
Bromine water
chloride
Cyclohexene
Calcium carbide
Ammoniacal solution of cuprous
V. PROCEDURE:
A. PROPERTIES OF ALKANES CYCLOHEXANE
1. Solubility and Density
Place 4 drops of cyclohexane in a vial and add 15 drops of water. Describe its
solubility and its density with respect to water.
Observation.
Explanation.
2. Flammability
Chem 31.1
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Place two drops of cyclohexane on a watch glass. Ignite with a matchstick.

What is the color of the flame?
Equation.
3. Reaction with Potassium Permanganate

Place 5 drops of a 1% solution of potassium permanganate to a vial and add
5 drops cyclohexane. Shake the mixture and observe.
Equation.
Explanation.
B. PROPERTIES OF ALKENES CYCLOHEXENE

Perform all three tests done in Part A using cyclohexene instead of
cyclohexane. Interpret and compare results. Write your observations,
equations and explanations below.
Chem 31.1
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C. PROPERTIES OF ALKYNES ACETYLENE

CAUTION: Acetylene is very combustible. Keep away all flames.
1. Preparation of Acetylene
Set up a gas generator for the reaction between calcium carbide and water.
Prepare three test tubes with corks filled with water. Have your setup
approved by the instructor before proceeding.
Let a few bubbles of gas escape first and ensure that no air left in the
apparatus. Collect three test tubes of acetylene gas by water displacement.
Observation.
Equation.
Chem 31.1
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38
2. Reaction with Potassium Permanganate

Add 5 drops of 1 % potassium permanganate in the test tube containing
acetylene gas. Observe. Describe and interpret results.
Observation.
Equation.
Explanation.
3. Reaction with Bromine Water

Add 1 mL bromine water to the second vial. Stopper and shake. Describe and
interpret results.
Observation.
Equation.
Explanation.
4. Formation of cuprous acetylide

To the third vial, add 5 mL of ammoniacal solution of cuprous chloride until a
brown precipitate is formed.
Observation.
Chem 31.1
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39
Equation.
e. Physical properties of Acetylene

Note some common physical properties of acetylene such as odor, color and
solubility with water.
POST-LAB:
1. Why are aliphatic hydrocarbons generally insoluble in water?
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
2. What is the difference in the reaction of cylohexane and cyclohexene
towards potassium permanganate solution? Explain.
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
3. Mention some safety precautions in the preparation of acetylene in the
lab.
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
4. Write a balanced chemical equation for the complete combustion of
paraffin wax (C25H52)
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Experiment No. 9
STEREOCHEMISTRY
Name: ______________________________________
Date: _____________
(refer to separate handout)
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Experiment No. 10
AROMATIC HYDROCARBONS
Name: ______________________________________
Date: _____________
I. PRE-LAB:
1. Differentiate aromatic from aliphatic hydrocarbons
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
2. Draw the structures of the following compounds.
a. m-chloronitrobenzene
b. 2,4,6-tribromoaniline
c. p-bromotoluene
Chem 31.1
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42
3. What is an o/p director? What is a m director?
II. OBJECTIVE:
To study some common physical and chemical properties of aromatic
hydrocarbons
III. APPARATUS:
Porcelain crucible
Burner
Thermometer
Vials
100 mL beaker
IV. MATERIALS:
Drops of benzene
1 % KMnO4 (faintly pink)
2 mL conc. Sulfuric acid
Cyclohexane
1 mL conc. Nitric acid
V. PROCEDURE:
1. Solubility
Note some physical properties of benzene. Test the solubility of 4 drops of
benzene in 15 drops of water. Note its relative density relative to that of
water.
What can be said about the solubility of benzene with water? Explain.
2. Flammability
Ignite 1 drop of benzene on a porcelain crucible. Write your observations.
Repeat the test with cyclohexane. Compare results.
Equations.
Chem 31.1
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43
3. Action of Nitric Acid

NOTE: WHEN USING NITRIC ACID WITH ORGANIC COMPOUND, ALWAYS
PROCEED WITH CARE, AS THE REACTIONS ARE SOMETIMES EXPLOSIVE.
WARNING: When temperature is beyond 60 0C, submerge the vial in water.
Prepare in a vial a mixture of 10 drops of concentrated sulfuric acid and 5
drops of concentrated nitric acid. Place the mixture in a water bath and heat.
When the temperature of the acid mixture is 55- 60 0C, add to it 6 drops of
benzene. Keep the mixture in the bath for 10 minutes, shaking it at short
intervals.
Observations.
Equation.
Repeat the test with cyclohexane. Which hydrocarbons reacted with nitric
acid?
What is the difference in the reaction of benzene and cyclohexane towards
conc. Nitric acid? Explain the difference.
What is the function of conc. Sulfuric acid in the nitration of benzene?

______________
4. Baeyers Test for Unsaturation
To 1-2 drops of benzene add 3 drops of 1 % (faintly pink) potassium
permanganate and shake.
Observations.
Explanation.
Chem 31.1
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POST-LAB:
1. Aside from benzene, give three other examples of aromatic compounds?
Cite some of their usage?
a.
__________________________________________________________________
__________________________________________________________________
__________________________________________________________________
b.
__________________________________________________________________
__________________________________________________________________
__________________________________________________________________
c.
__________________________________________________________________
__________________________________________________________________
_________________________________________________________________
2. What makes benzene a stable compound?
3. Is aniline an o/p or a m director? What about nitrobenzene?
4. Both aniline and nitrobenzene are nitrogen-containing aromatic

compounds. Why is one o/p directing and the other m?
5. Write the mechanism of the reaction of nitration of benzene?
Chem 31.1
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Experiment No. 11
ALCOHOLS AND PHENOLS
Name: ______________________________________
Date: _____________
I. PRE-LAB:
1. Concentration of alcohol is often expressed as proof. How strong is an 80
proof alcohol?
2. Draw the structures of the following compounds
a. 4-chloro-2-butanol
b. 1,4-butanediol
c. 2-propen-1-ol
d. 2-methylcyclopentanol
3. Compare the boiling points of phenol and methylcyclohexane. Explain the
differences of their boiling points.
______________________________________________________________________________
______________________________________________________________________________
Chem 31.1
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46
______________________________________________________________________________
______________________________________________________________________________
II. OBJECTIVE:
To study some common physical and chemical properties of alcohols
and phenols
III. APPARATUS:
Bunsen burner
100 ml Beaker
Thermometer
Vials
Microspatula
Water bath
IV. MATERIALS:
Test for alcohols
Calcium carbide
Anhydrous copper (II) sulfate
95 % ethyl alcohol
Iodine in KI
3 drops of 8 N NaOH solution
Lucas reagent
Ethyl alcohol
Isopropyl alcohol
Tert-butyl alcohol
10 % potassium dichromate
Dilute sulfuric acid
Test for Phenols
3 % sodium bicarbonate
1 % iron (III) chloride
2 % acetic acid solution
0.1 % phenol solution
resorcinol
salicylic acid
1-butanol
V. PROCEDURE:
A. ALCOHOLS
1. Iodoform Test
To 4 drops of ethyl alcohol in 1 mL water, add 3 drops of 8 N NaOH solution,
then dropwise a solution of iodine in KI until a faint yellow color persists.
Warm the mixture in a water bath at about 60 0C. Set aside for 5-10 minutes.
Repeat the test using isopropyl alcohol and tert-butyl alcohol instead of ethyl
alcohol.
Chem 31.1
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47
Observations.
Equation:
Explanation.
2. Oxidation
Put 5 drops of each ethyl alcohol, isopropyl alcohol, t-butyl alcohol in 3
separate vials. To each add 5 drops of 10 % potassium dichromate and 5
drops of dilute sulfuric acid solution. Warm in a water bath. Note the color of
the solutions. Compare the ease by which each of the alcohols is oxidized.
Observations.
Equations.
Explanation.
3. Substitution Reaction
Into three separate vials put 5 drops each of ethyl alcohol, isopropyl alcohol
and t-butyl alcohol. Add an equal amount of Lucas reagent (ZnCl2 HCl) to
each. Shake for a few minutes at room temperature and allow to stand.
Observe closely. Cloudiness in the solution is first sign of a reaction. Take
note of the time at which the cloudiness of the solution is observed.
Observation.
Chem 31.1
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48
Equations.
Explanation.
POST-LAB:
1. Alcohols are more soluble in water than hydrocarbons are in water. Why?
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
2. Why does the rule for solubility for alcohols depend upon their molecular
size?
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
3. Write the structures and names of the isomeric 5-carbon saturated
alcohols. How would they react with Lucas reagent?
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
4. Propose a mechanism for the reaction of alcohols with Lucas reagent.
Chem 31.1
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B. PHENOLS
Phenols are compounds that have the hydroxyl group attached to an aromatic
ring. Thus, phenol is the specific name for hydroxybenzene, itself; -- and it is
the general name for the family of compounds derived from
hydroxybenzene. Pure phenol is a white crystalline solid, mp 42o.
Caution: The solid, or concentrated solutions of phenol can cause painful
burns if allow to come into contact with the skin. If spilled on the skin, it
should be removed at once with water and then with alcohol. Then, rub
cotton that is wet with alcohol on the skin. Repeat with dilute solution of
Na2CO3. Finally, put a layer of ointment for burns on the affected skin.
1. The Acidity of Phenols
As a class, phenols are considered to be weak acids, and therefore, react
with and dissolve in strong bases; like sodium hydroxide. However, they do
not dissolve in the weak base, sodium bicarbonate, NaHCO3.
Ar OH
+
NaHCO3
a weak acid a weak base
Ar OH
+
NaOH
a weak acid a strong base
N.R.
Ar O Na + H2O
Test each of these compounds (phenol, resorcinol, salicylic acid, ethyl alcohol)
by adding small amount (about 0.1g) to a few drops of:
Chem 31.1
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(1) dilute NaOH, and

(2) dilute NaHCO3
Bubbles of CO2 indicate positive result. Compare the relative acid strengths of
the compounds tested above.
Observations.
Equations.
2. Ferric Chloride Color Test

Many phenols and related enolic compounds form colored coordination
compounds with ferric ions. It is believed by some that six molecules of a
monohydric phenol are associated with one ferric ion in the complex.
6 Ar
OH +
FeCl3
Fe(Ar O)63- 3 Cl
+ 6H
Place 5 drops of 0.1 % solution of phenol in a vial and add 1 drop of freshly
prepared 1 % ferric chloride solution. As a control, add 5 drops of 1% FeCl3 to
water in another vial.
Instead of using phenol, repeat with
a. Resorcinol
b. Salicylic acid
c. 1-butanol
Observations.
Chem 31.1
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51
Explanations.
3. Oxidation of Phenols
In a small test tube place 5 drops of a 0.5 percent aqueous potassium
permanganate solution. Add an equal volume of a 5 percent aqueous
solution of phenol. If necessary, warm the solution in a hot water bath, and
shake it vigorously. What evidence is there that an oxidation has taken
place?
Observations.
Equations.
Questions:
Describe any changes in the appearance of the reaction mixture. What
evidence did you observe that suggested that an oxidation had taken place?
The dark, solid residue is the reduced product of the oxidizing agent. What is
it?
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
POST-LAB
1. Draw the structures of the following compounds.
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Experiment No. 12
ALDEHYDES AND KETONES
Name: ______________________________________
Date: _____________
I. PRE-LAB:
1. What is the general formula for an aldehyde? A ketone?
2. Write the structures of the following compounds
a. 2-methylcyclopentanone
b. 4-hexen-2-one
c. o chlorobenzaldehyde
Chem 31.1
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53
d. 2-methyl-3-pentenal
II. OBJECTIVE:
To study some common physical and chemical properties of aldehydes
and ketones
III. APPARATUS:
Bunsen burner
100 mL beaker
3 test tubes
Vials
Test tube holder
Thermometer
IV. MATERIALS:
Drops of:
Acetaldehyde
Acetone
2, 4-dinitrophenylhydrazine
Fehlings A
3M H2SO4
Benzaldehyde
1% KMnO4
Tollens reagent
Fehlings B
Very dilute KMnO4 (faintly pink)
V. PROCEDURE:
Perform all
the following tests on each of the following carbonyl compounds:

Acetaldehyde (an aliphatic aldehyde)
Benzaldehyde (an aromatic aldehyde)
Acetone (a ketone)
A. PHYSICAL PROPERTIES
Note some physical properties of the carbonyl compounds. Test the solubility
of 3 drops of the carbonyl compound with 10 drops of water.
Compound
Observations
Acetaldehyde
Benzaldehyde
Acetone
Explanation.
Chem 31.1
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B. CHEMICAL PROPERTIES
1. Reaction with 2,4 dinitrophenylhydrazine
Add 5 drops of the carbonyl compound to 5 drops of 2,4dinitrophenylhydrazine. Shake the mixture. Nearly all dinitrophenylhydrazine
precipitate immediately but in few cases they must be allowed to stand for
about 15 minutes.
Observation.
Explanation.
Equations.
Chem 31.1
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55
2. Reaction with Tollens Reagent

Add 5 drops of the carbonyl compound to 5 drops of an ammoniacal solution
of silver nitrate or Tollens reagent in a test tube. Mix thoroughly and heat
gently in a water bath for 10 minutes. Set aside at least 10 minutes.
Observations.
Explanation.
Equations.
3. Fehlings Test
In a vial, mix 5 drops of Fehlings solution A and 5 drops of Fehlings solution
b. Add 5 drops of the carbonyl compound and warm in a water bath.
Observation.
Explanation.
Equations.
Chem 31.1
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4. Benedicts test
Place 1.0 mL of Benedicts solution to three separate tubes containing the
carbonyl compounds. Place the test tubes in hot water bath.
Observation.
Explanation.
Equations.
5. Iodoform Test
To 4 drops of the carbonyl compound in 1 mL water, add 3 drops of 8 N NaOH
solution, then dropwise a solution of iodine in KI until a faint yellow color
persists. Warm the mixture in a water bath at about 60 0C. Set aside for 5-10
minutes.
Observation:
Explanation.
Equation:
POST-LAB:
1. Give the composition of the following reagents:
Chem 31.1
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Tollens reagent
Fehlings A
Fehlings B
2. Cite an industrial application of Tollens Test

______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
Experiment No. 13
CARBOXYLIC ACIDS AND ITS DERIVATIVES
Name: ______________________________________
Date: _____________
I. PRE-LAB:
Draw the structures of the following compounds that will be used in the lab:
a. Acetic acid
b. Oleic acid
c. Formic acid
d. Stearic acid
e. Succinic acid
f. Lactic acid
Chem 31.1
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g. Butyric acid
II. OBJECTIVE:
To study some common physical and chemical properties of carboxylic
acids
III. APPARATUS:
Bunsen burner
Microspatula
Vials
Test tube holder
IV. MATERIALS:
Drops of:
Acetic acid
Oleic acid
Formic acid
Pinch of:
Stearic acid
Succinic acid
Very dilute KMnO4
butyric acid
Lactic acid
10 % sodium bicarbonate
Benzoic acid
Oxalic acid
V. PROCEDURE:
1. Solubility in Water
Test the solubility in water of the following acids. Use 3 drops of the liquid or
one microspatula of solid to 10 drops of water.
Observations
Acetic acid
Stearic acid
Benzoic ac id
Explanation.
Chem 31.1
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2. Reaction with 10 % Sodium Carbonate

Test the reaction of the acids used above in 10 % sodium carbonate solution.
Note the evolution of gas.
Observations.
Equations.
3. Action of an Oxidizing Agent on the Carbonyl Group

Place 5 drops of each of acetic, lactic, succinic, formic, benzoic and oxalic
acids in separate test tubes and add 1 mL of 0.5 % potassium permanganate
to each tube. Heat the test tubes in a water bath and note if any reduction of
the permanganate occurs.
Observations.
Chem 31.1
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Equations.
Explanation.
POST-LAB:
1. Arrange the following compounds in order of increasing boiling point. (All
of the compounds have about the same molecular weight.)
1-pentanol, hexane, butanoic acid, pentanal
2. Which member of each of the following pairs of compounds would you

expect to have a higher solubility in water? Why?
a. 2-butanone or propanoic acid
________________________________________________________________________
________________________________________________________________________
________________________________________________________________________
________________________________________________________________________
b. hexanoic acid or ethanoic acid
________________________________________________________________________
________________________________________________________________________
________________________________________________________________________
________________________________________________________________________
Chem 31.1
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3. Identify the common carboxylic acid described below. Choose answers

from the box. Then, draw the structures of the carboxylic acids in the space
provided below.
acetic acid
butyric
acid
acid
para-Aminobenzoic aid (PABA)
monosodium glutamate (MSG))
citrus acid
malic acid
niacin
oxalic
formic acid
__________________ a. A component of the venom of ants and caterpillars;

produced in
the body when methanol is consumed
__________________ b. the acid found in vinegar
__________________ c. This acid has a foul, rancid odor; produced from the
breakdown of
soft triglycerides in butter
__________________ d. Found in citrus fruits (lemons, grapefruit, oranges, etc.);
commonly used in buffering solutions with sodium
citrate
__________________ e. Found in many leafy green plants such as rhubarb and
spinach;
combines with calcium ions in the body to produce
insoluble salts, which form kidney stones
__________________ f. Used in sunscreens; absorbs short-wavelength UV light.
__________________ g. Responsible for the sharp taste of apples (genus Malus)
Chem 31.1
UP Cebu
62
__________________ h. A water-soluble, B-Complex vitamin obtained from fish,

green
vegetables, lean meat, poultry, whole-grain and enriched
bread and cereal; produced in the body from
tryptophan; essential for growth, healthy tissues, the
production of energy from carbohydrates, and the
production of fats
__________________ i. Added to some foods to enhance their meaty flavor
Experiment No. 14
ESTERS
Name: ______________________________________
Date: _____________
I. PRE-LAB:
1. What is the general formula of an ester?
2. Give the IUPAC name and common name of the following esters
IUPAC Name
Common Name
a. H C O CH2CH3
II
O
H
O
I
II
b. CH3 C O C CH3
I
CH3
O
II
c. CH3 C O CH2CH2CH2CH3
Chem 31.1
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63
II. OBJECTIVE:
To study some physical and chemical properties of esters
III. APPARATUS:
Bunsen burner
100 mL beaker
Test tube holder
Vials
Test tube
IV. MATERIALS:
Drops of:
Ethyl alcohol
Methyl salicylate
Ethyl acetate
Acetic acid
Amyl acetate
Methyl benzoate
Litmus paper
V. PROCEDURE:
1. Preparation of an Ester
To a solution of 5 drops of ethyl alcohol in a dry vial add 10 drops of acetic
aicd and very carefully 5 drops of conc. sulfuric acid. Warm the mixture very
gently in a water bath. Notice the characteristic odor. What is the ester
formed?
Observation.
Equation.
2. Odor / Uses
Note the characteristic odor and uses of the following esters:
Chem 31.1
Methyl salicylate
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64
Ethyl acetate
Amyl acetate
Methyl benzoate
Ethyl benzoate
3. Solubility and Density

Test the solubility of 5 drops of each ethyl acetate and methyl salicylate in 10
drops of water. Describe relative densities.
Observation.
4. Hydrolysis of an Ester
Put 5 drops of amyl acetate in a vial and test with blue litmus paper. Add 10
drops of water. Shake the vial and warm in a water bath. Test with litmus
again.
Observation.
Equation.
POST-LAB:
1. Define esterification and neutralization. Is there a difference between the
two?
Chem 31.1
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65
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
2. What can be said about the solubility of esters in water? Explain.
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
3. What are the products during hydrolysis of an ester?
______________________________________________________________________________
______________________________________________________________________________
Experiment No. 15
AMINES AND AMIDES
Name: ______________________________________
Date: _____________
I. PRE-LAB:
1. Arrange the following compounds in order of increasing boiling point. (All
of the compounds have about the same molecular weight.
propanoic acid, diethylamine, 1-butanol, ethyldimethylamine
Answer:
____________ , ______________ , ______________
, ______________
2. Draw the structures of the following compounds. For each of the amines
and amides below label them as primary, secondary or tertiary.
a. Trimethylamine
b. N-methyl-2-chloroaniline
c. Ethanamide
Chem 31.1
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66
d. N-ethyl-N-methylacetamide
II. OBJECTIVE:
To study some common physical and chemical properties of amines
and amides
III. APPARATUS:
Vials
Test tube holder
Watch glass
Stirring rod
IV. MATERIALS:
Drops of:
Aniline
Conc. Hydrochloric acid
Urea crystals
1% Copper (II) sulfate
5 %sodium nitrate
dilute ferric chloride

conc. Nitric acid
8N sodium hydroxide
blue and red litmus paper
ice
V. PROCEDURE:
A. AROMATIC AMINES ANILINE
1. Solubility / Basicity
Shake 3 drops of aniline with 5 drops of water. Observe. Test the solution with
litmus paper. What do you observe?
To the above solution, add 3 drops of very dilute ferric chloride solution. Note
the color.
Equation.
Chem 31.1
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67
2. Salt Formation
Mix mL of aniline with a slight excess of concentrated HCl. Observe the
change in color.
Equation.
3. Diazotization
Place 2 mL of aniline in a test tube, add 10 mL of water and 4 mL of conc
HCl. Shake and cool to 50C in an ice bath, then add a cold solution of 5 %
NaNO2 solution. Keep the mixture in an ice bath.
Observation.
Equation.
4. Effect of NH2 Group on the substitution in the Benzene Ring

Add bromine water dropwise with shaking to a mixture of 3 drops of aniline
and 2mL water.
Observations.
Would benzene react with bromine without a catalyst?
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
What is the effect of the - NH2 group on substitution in the benzene ring?
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
Chem 31.1
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68
Equation.
B. AMIDES UREA
1. Solubility
Test the solubility of 1 microspatula of urea in 10 drops of water.
Observations.
2. Formation of Urea Nitrate

Dissolve 1 microspatula of urea in 1 drop of water. Add two drops of conc.
nitric acid.
Observations.
Equation.
3. Biuret Formation
Place 5 microspatula of dry urea crystals in a dry pyrex vial and heat to a
high temperature in 5 minutes. While heating, test the vapors with moist red
litmus paper. Observe. Cool the vial and examine the residue.
Observations.
Explanation.
Equation.
Chem 31.1
UP Cebu
69
4. Biuret Test
Dissolve the residue from number 3 in 4-5 drops of water. (Warm if solid will
not dissolve). Add an equal volume of 8 N NaOH solution and one drop 1 %
CuSO4. Note the color.
Observation.
Explanation.
Repeat the test using 2 microspatula of unheated urea in 15 drops of water.

Compare the results obtained in the two vials. Describe and interpret results.
Observation.
Explanation.
POST-LAB:
1. In diazotization, what is the purpose of cooling the system thoroughly?
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
2. Amines are responsible for the nasty odor of many substances including
the odor of fish. Explain why lemon juice might remove the odor of fish.
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
Chem 31.1
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70
Experiment No. 16
ESTERIFICATION REACTION: PREPARATION OF ASPIRIN
Name: ______________________________________
Date: _____________
Aspirin (chemical name: acetylsalicylic acid), is a compound widely

used as a pain killer and fever reducer. Salicylic acid, whose name comes
from Salix, the willow family of plants, was derived from willow bark extracts.
In folk medicine, willow bark teas were used as headache remedies and
other tonics. Nowadays, salicylic acid is administered in the form of aspirin
which is less irritating to the stomach than salicylic acid. To prepare aspirin,
salicylic acid is reacted with an excess of acetic anhydride. A small amount
of a strong acid is used as a catalyst which hastens the reaction. In this
experiment, sulfuric acid will be used as the catalyst. The excess acetic acid
will be quenched with the addition of water. The aspirin product is not very
soluble in water so the aspirin product will precipitate when water is added.
The synthesis reaction of aspirin is shown below:
Chem 31.1
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Since acetic acid is very soluble in water, it is easily separated from the
aspirin product. The aspirin isolated in this step is the crude product. A
purified product can be obtained through recrystallization of the crude
product in hot ethanol.
I. PRE-LAB:
Cite uses of aspirin.
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
II. OBJECTIVE:
Synthesize aspirin from its corresponding acid anhydride and alcohol
III. APPARATUS:
2 pc. 125-mL Erlenmeyer flask
Test tubes
Bunsen burner
Platform balance
Filter paper
Water bath
Watch glass
Ice
Stirring rod
IV. MATERIALS:
Salicylic acid
Acetic anhydride
Concentrated sulfuric acid
V. PROCEDURE:
1. In a 125-mL Erlenmeyer flask, place 1.0 g of salicylic acid, 2.0 mL of acetic
anhydride and 1-2 drops of concentrated sulfuric acid, added in that order
(note a and b).
2. Swirl the mixture and note that the reaction is exothermic. When the
reaction has abated somehow, heat the flask in a beaker of boiling water for
5-6 minutes (note c)
3. Add 10 mL of ice water and swirl to aid the hydrolysis of excess acetic
anhydride (note d).
Chem 31.1
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4. Cool the mixture thoroughly and collect the crystals by suction filtration.
Let it dry and weigh the mass of crude product (aspirin) obtained.
5. The crude acetylsalicylic acid is purified by recrystallization. It is dissolved
in hot methanol or ethanol (6 mL). The resulting solution is poured into 20
mL of hot water. If a precipitation occurs, heat the mixture until complete
dissolution and then let it cool down slowly. After recrystallization, the solid is
filtered and dried. Weigh the mass of pure product (aspirin) obtained.
6. Compute for the % recovery of crude and pure aspirin.
Notes:
a. Concentrated sulfuric acid can undergo quite a number of reactions with
organic compounds. It can add to an alkene, substitute on an aromatic ring,
dehydrate an alcohol, polymerize an alkene, transform an alcohol into n
ether, or simply protonate basic atoms such as oxygen or nitrogen. As a
catalyst in this reaction, H2SO4 is supposed to protonate an oxygen, so just a
drop or two should be used.
b. If acetic anhydride is in contact with concentrated sulfuric acid for a
period of time, it may hydrolyzed to acetic acid. If salicylic acid is in contact
with concentrated sulfuric acid, for a period of time, various reactions may
occur, such as sulfonation of benzene ring.
c. Heating will evaporate some of the acetic acid produced. This will move
the equilibrium more to the right, pushing the reaction to completion.
(CH3CO)2O +
H2O
2CH3COOH
d. Charcoal may be added if the product is colored.

e. To crystallize the aspirin, water is added; water increases the polarity of
the ethanol, which decreases the solubility of the aspirin in the mixed solvent
and thus effectively crystallizing it at low temperature.
Write the balanced equation for the synthesis of aspirin below. Give the
name of the reactants and products involved in the reaction.
Chem 31.1
UP Cebu
73
Weight of dry aspirin (actual yield): ________________

Calculate the theoretical yield.
Calculate the percentage yield.
If percent yields were not 100%, explain below where the missing material
might have gone (or where extra material might have come from).
POST-LAB
1. What would be the effect of the following on the percentage yield of
aspirin?
a. Addition of dilute sulfuric acid instead of concentrated sulfuric acid
________________________________________________________________________
________________________________________________________________________
b. Using a base, e.g. NaOH, instead of concentrated sulfuric acid
________________________________________________________________________
________________________________________________________________________
c. Dissolving the crystals in hot water only
________________________________________________________________________
________________________________________________________________________
Chem 31.1
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2. When aspirin (acetylsalicylic acid) is heated in boiling water, it

decomposes. The resulting solution gives a positive FeCl3 test. Why is the test
positive? What is the reaction? Give an equation for the reaction?
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
3. Will CH3COCl be a better starting material than the anhydride? Justify your
answer.
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
______________________________________________________________________________
4. If one were to use 5.0 g salicylic acid and an excess of acetic anhydride in
the above synthesis of aspirin, what would be the theoretical yield of
acetylsalicylic acid in moles? In grams? Show your solution.
Chem 31.1
UP Cebu

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1

Pinch of the following:

broken crucible, heat strongly each of the following:

Write observations and classify each substance as to organic or inorganic

What element is common to all organic compounds? _______________.

FeSO4 + H2SO4 + KMnO4

COMPOSITION OF MOST ORGANIC COMPOUNDS

Clay flame shield

A good (suitable) recrystallization solvent will dissolve a large amount

= grams mass of original solid x percent

= g (solid) g (solid lost)

= g (solid recovered) x100 / g (solid)

Place 5 grams of impure acetanilide (90 % acetanilide + 10 % NaCl and trace

2. Why must the filtration be carried out quickly?

Test for Chlorides:

2. What is meant by saying the two liquids are immiscible?

100C (g/10 mL)

1. What volume of boiling water is needed to dissolve the 10 g of Compound A?

3. Combustion analysis of caffeine gives the following composition: 49.68 %

The melting point of a compound is the temperature at which it

degree of purity can be made by comparing melting characteristics

Figure 6.1. Melting Point Apparatus

Determine the melting point range of an unknown solid given by your

Melting Point (oC)

Melting point range of unknown:

The boiling point of a compound is the temperature at which it

Figure 7.1: Boiling Point Apparatus

Melting Point range of water:

Melting Point (oC)

Boiling point range of unknown:

Place two drops of cyclohexane on a watch glass. Ignite with a matchstick.

3. Reaction with Potassium Permanganate

B. PROPERTIES OF ALKENES CYCLOHEXENE

C. PROPERTIES OF ALKYNES ACETYLENE

2. Reaction with Potassium Permanganate

3. Reaction with Bromine Water

4. Formation of cuprous acetylide

e. Physical properties of Acetylene

(refer to separate handout)

3. What is an o/p director? What is a m director?

3. Action of Nitric Acid

What is the function of conc. Sulfuric acid in the nitration of benzene?

2. What makes benzene a stable compound?

3. Is aniline an o/p or a m director? What about nitrobenzene?

4. Both aniline and nitrobenzene are nitrogen-containing aromatic

5. Write the mechanism of the reaction of nitration of benzene?

(1) dilute NaOH, and

2. Ferric Chloride Color Test

the following tests on each of the following carbonyl compounds:

2. Reaction with Tollens Reagent

2. Cite an industrial application of Tollens Test

2. Reaction with 10 % Sodium Carbonate

3. Action of an Oxidizing Agent on the Carbonyl Group

2. Which member of each of the following pairs of compounds would you

3. Identify the common carboxylic acid described below. Choose answers

__________________ a. A component of the venom of ants and caterpillars;

__________________ h. A water-soluble, B-Complex vitamin obtained from fish,

3. Solubility and Density