Date Performed: __________________ Score: _________

Learning Activity No. 1

DETERMINATION OF MELTING POINT

Specific Learning Objectives :

At the end of the experiment the students can:

1. determine the melting points of the organic compounds assigned.

2. compare the difference in melting points between a pure sample and an impure
sample.

Time Allotment : 3 hours

Learning Resources
Materials and Reagents:
acetyl salicylic acid sucrose
cinnamic acid urea
salicylic acid
pure cooking oil

Apparatus: melting point tubes, test tubes, 250 mL beaker, wire gauze, rubber
Band, bunsen burner, thermometer, iron stand, iron clamps, stirrer

Learning Strategies

CRITERIA OF PURITY

A pure substance is a system of molecules which upon exhaustive fractionation fails to yield fractions
with different properties. A number of constants can be measured in order to establish the purity of
organic substances; among these are melting point, boiling point, refractive index, density, solubility,
etc. For most solid compounds melting point or freezing point is usually determined and for most
liquid compounds, boiling point and refractive index.

MELTING POINT

A pure crystalline organic compound has a definite and sharp melting point – the temperature at
which the liquid and solid phases exist in equilibrium with each other at a pressure of one
atmosphere. Thus, when a pure crystalline substance is heated slowly and begins to melt without
decomposition, the temperature remains constant until all the solid has melted. At this temperature,
if heat is removed the liquid changes into a solid, if heat is applied into the system, all the solid
changes to liquid. Thus the melting and freezing points of a pure crystalline substance are identical.

For a pure organic compound the difference between the temperature at which the crystals collapse
and the temperature at which the sample completely liquefies, does not exceed 0.50C. This is the
melting point range. Any small quantity of miscible and partially miscible impurity will usually
produce a marked increase in the melting point range. Melting of an impure substance usually starts
at a temperature lower than the melting point of the pure compounds. Melting point is therefore a
valuable criterion of purity for an organic compound.

Set-up:
Learning Content

COMPARISON OF THE MELTING POINT OF A PURE SUBSTANCE AND A MIXTURE OF SUBSTANCES

Approximate Determination of Melting point:

1. Put a few crystals on the bulb of a thermometer.

2. Place the thermometer lying horizontally over a wire gauze.
3. Observe the temperature at which the crystal melts.
4. Use this as a guide (approximate melting point) when the actual determination is done.

Melting Point Determination of Pure and Impure Sample

1. Pulverize the sample to a fine powder on a watch glass using the back of a porcelain scoop or a
pestle.
2. Form a heap of the pulverized sample.
3. Press the open end of the melting point tube into it and tap the closed end of the tube against
the table or allow the melting point tube to drop through about 30 to 60 cm of glass tubing, held
vertically with one end resting on the table, so as to pack 5 – 6 cm of the sample at the sealed
end.
4. With a rubber band , attach the melting point tube to a thermometer so that the solid is
alongside the mercury bulb.
5. Immerse the thermometer 2 – 3 cm in the cooking oil bath.
6. Heat the oil bath rapidly to within 150C of the melting point of the compound then adjust the
burner flame so that the bath temperature rises at a rate of about 20 C per minute.. Use a stirrer
to keep the bath uniformly heated.
7. Note the temperature at which the solid starts to liquefy and that at which it is completely
liquefied. Note this melting point range and record these two temperatures to the nearest 0.10C.

NOTE:
1. The pulverized sample must be kept dry and free from impurity.
2. Attach simultaneously 2 melting point capillaries, one containing the pure sample and the other, a
mixture (1:1) of the sample with another. Observe these two simultaneously.
3. Use the same immersion line for all determination.
4. Use a dry beaker and keep the oil free from water. The oil may be used again as long as it is
kept clean and dry.
 5. A sample of your unknown will be given to you by your instructor together with three numbers
corresponding to the set of organic compound used. One of these numbers corresponds to your
unknown.

Data and Results

Sample Approximate Melting Observed Melting Literature Melting

Point Point Range Point
Acetyl salicyclic acid

Cinnanic acid

Salicylic acid

Sucrose

Urea

Impure sample

Unknown sample

Conclusion: (Give explanation for all your observations.)

Learning Evaluation

1. Research the expected melting points of each of the following compounds given.

2. Write the structural formula and uses of each of the compounds given.
Date Performed: _____________________ Score: _____

Learning Activity No. 2

DETERMINATION OF BOILING POINT

Specific Learning Objectives

At the end of the experiment the students can:

1. determine the boiling points of the assigned compounds

2. compare the difference in boiling point between a pure sample and an impure sample

Time Allotment: 3 hours

Learning Resources
Reagents/Materials:
Pure samples of the following:

Acetone mixtures of any of the above

Ethanol cooking oil

APPARATUS: Capillary tubes 20 – 30, small test tubes, 250 mL dry beaker, thermometer (0 –
2500C, 1 0 C scale division), stirrer, wire gauze, Bunsen burner, iron stand, clamps

Learning Strategies

The boiling point of an organic compound which can be distilled without decomposition may be
used as a criterion of its purity. The boiling point of a liquid may be defined as the temperature
at which the vapor pressure is equal to the external pressure exerted at any point upon the liquid
surface. In general, boiling point data are reported for 760 mmHg or 1 atm except in cases of
vacuum distillation where data are reported for the pressures at which the distillations were
conducted.
Since boiling point varies with atmospheric pressures, the observed boiling point is not a reliable
criterion as the melting point. To compare observed boiling point data with literature data, it is
necessary to make corrections due to atmospheric pressure difference.

Learning Content

COMPARISON OF THE BOILING POINT OF A PURE SUBSTANCE AND AN IMPURE

MATERIAL

Approximate Determination of Boiling Point

1. Place 1 mL of the liquid sample in a test tube. Heat in the flame of a burner (
CAUTION): The liquid may be flammable) until a ring of condensing liquid appears about
halfway up the test tube while holding a thermometer with its bulb at the level of the
condensing liquid.
2. The reading on the thermometer gives the approximate boiling point of the liquid.
3. Record the temperature in the data table.

Boiling point determination

1. Introduce a small quantity of the sample 0.25 – 0.5 mL in the boiler tube. Insert a
capillary tube, open end first into the boiler tube.
 2. Attach the tube to the thermometer by a rubber band so that the liquid is alongside the
mercury bulb.
3. Immerse the thermometer and boiler tube into the oil bath 2 -3 cm deep.
4. Heat the bath and raise the temperature rapidly until it is 10 – 150 C below the
approximate boiling point. Use the wire stirrer to keep the bath uniformly heated.
5. Continue heating more slowly until a rapid and continuous stream of bubbles comes out
from the capillary.
6. Remove the flame and allow the bath to cool slowly with occasional stirring (10C
drop/min). Note the temperature at which the bubbling ceases and the liquid just starts
to rise the capillary tube. Record this temperature to the nearest 0.10C.
7. Immediately reheat the oil ( 10C rise/min), with occasional stirring, to rise the
temperature within the range of the boiling point. Note the temperature at which the
first bubbling starts from the capillary.
8. Record the temperature to the nearest 0.10C. The two temperature readings represent
the boiling point range of the substance.

DETERMINATION OF THE BOILING POINT OF AN UNKNOWN SAMPLE.

1. Ask an unknown liquid sample from your instructor.

2. Determine the boiling point ranges and note the barometric pressure.
3. Record the observed boiling point in the data table.

Data and Results

Sample Approximate Boiling Observed Boiling Expected Boiling

point point range Point Range
Acetone

Ethyl alcohol

Impure

Unknown

Conclusion

Learning Evaluation

1. Research the expected boiling points of the given compounds.

2. Write the structural formula of the compounds and give their uses.
Date Performed: _____________________ Score: _________

Learning Activity No. 3

PURIFICATION OF SOLIDS BY CRYSTALLIZATION

Specific Learning Objectives

At the end of the experiment the students can:

1. purify solids through crystallization.

2. choose a proper solvent for the process.

Time Allotment: 3 hours

Learning Resources

Reagents/Materials:
Acetanilide ethanol
benzene activated charcoal

Apparatus: filter paper, balance, test tubes, 10 mL graduated cylinder, microspatula,

evaporating dish, funnel, medicine droppers, tripod, glass rod, Bunsen burner,
wire gauze, iron stand Erlenmeyer flask

Learning Strategies

Recrystallization

Products from an organic reaction are seldom obtained in a pure state directly from the reaction
mixture. If the product is a solid, it may be purified by recrystallization from a suitable solvent.
The process of crystallization depends on the fact that most organic compounds are more soluble
in hot solvents than in cold, and that the impurities present will have different solubilities from
the desired compounds. The procedure involves:

(a) dissolving the impure material in a minimum amount of hot solvent (if too much solvent is
added, the excess can be boiled off),
(b) filtering the hot solution at its boiling point to remove insoluble impurities when present (this
filtration is required only when insoluble impurities are observed),
(c) allowing the solution to cool and deposit crystals of the compound,
(d) filtering the crystals from the solution (called the mother liquor,
(e) washing the crystals with a little cold solvent to remove the mother liquor, and
(f) drying the crystals to remove the last traces of solvent.

In this experiment, recrystallization from a single solvent (water) will be illustrated.

Properties of an Ideal Recrystallizing Solvent

If recrystallization is to be effective, the solvent must be properly selected. A good

recrystallization solvent should:
(a) dissolve a moderate quantity of the substance to be purified at an elevated temperature, but
only a small quantity at low temperatures
(b) not react with the substances to be purified
(c) dissolve impurities readily at a low temperature or not dissolve them at all
(d) be readily removable from the purified product.

This last requirement usually means that the solvent must have a relatively low boiling point and
evaporate readily.

Learning Content

Set - up

Choice of Solvent for Crystallization

1. Place a small amount of acetanilide, about the size of a corn grain in three separate
test tubes. Label each.
2. Add 1 mL of water in one of the test tubes. Shake the test tube and warm in water
bath. Observe and record.
3. If undissolved, add 1 mL more of the water and warm. Shake the test tube and
observe the results. Cool and set aside.
4. Repeat the procedure with other solvents – methanol and benzene.
5. Cool the contents of the three test tubes. Record and observe the results.
Crystallization of an impure organic compound by the use of two miscible solvents.

1. Weigh about 0.5 g of impure acetanilide and record.

2. Carefully transfer the weighed acetanilide in a test tube and add 2 mL ethanol.
3. Heat in water bath until it boils.
4. If the solid is not completely dissolved, add more ethanol.
5. Add about 0.5 gram of activated charcoal if the solution is colored, then continue
heating for a few minutes.
 6. Prepare fluted filter paper to fit the funnel ( see figure above). Pass through 5 mL hot
water then 5 mL hot ethanol. Drain on receiving beaker.
7. Filter the hot solution through the warm filter paper draining down to a beaker.
Discard filter paper after use.
8. Add about 3 mL of hot water dropwise on to the hot filtrate until cloudiness disappears.
Reheat. Allow the filtrate to cool to room temperature.
9. Filter the crystals through another fluted filter paper previously weighed.
10. Wash the crystals with cold water. Dry crystals.

Data and Results:

Choice of Solvent for Crystallization

Solute Solvent Observation

Acetanilide Water

Acetanilide Benzene

Acetanilide Ethanol

Crystallization of an Impure organic Compound by the Use of Two Miscible Solvents

Describe the crystals in Observation

terms of

Conclusion

Learning Evaluation

Enumerate the properties of an ideal recrystallizing solvent

Date Performed: _____________________ Score: ________

Learning Activity No. 4

PURIFICATION OF SOLIDS BY SUBLIMATION

Specific Learning Objectives:

At the end of the experiment the students can:

1. purify organic solids through sublimation

2. determine the weight of the obtained sublimate.
3. calculate the percentage of the pure crystals recovered from the sample.

Time Allotment: 2 hours

Learning Resources
Reagents/Materials:
Acetanilide Benzoic acid Naphthalene

Apparatus: filter paper, watch glass (10 cm and 12 cm), microspatula, funnel, tripod, wire gauze,
air bath, Bunsen burner, iron stand

Learning Strategies:

When an impure organic solid is heated, the vapor pressures of all the components are increased.
If the vapor pressure of the major component rises more rapidly than that of the impurity so that
this vapor pressure equals one atmosphere before the melting point of this component is
reached, the solid will pass into vapor without intermediate passage through the liquid state. By
cooling, the vapor is converted to crystals which have high degree of purity. This process is
known as sublimation.
Only a few compounds with relatively high vapor pressure can be purified by sublimation under
normal pressure. These include naphthalene, anthracene, benzoic acid, salicylic acid, alpha and
beta naphthol, camphor, iodoform and acetanilide. The process yields products of high purity,
but considerable loss of products may occur.

Learning Content

1. Weigh about 0.5g of impure sample. Record the weight to the nearest 0.01 g.
2. Spread the sample on the 12 cm watch glass leaving a margin at the edge.
3. Cover with an inverted 10 cm watch glass which has been previously weighed to the
nearest 0.01 g.
4. Heat the watch glass with the sample over an air bath using a 5 cm sized flame.
5. cool the center top of the inverted watch glass with a 25 mm filter paper disc kept moist
with 2 or 3 drops of water.
6. When a film is formed on the condensing surface, adjust the flame so that condensation
proceeds very slowly over a period of 30 min. The set-up is inspected occasionally until
most of the sample has vaporized.
7. When no more crystals appear to sublime, cool the set-up. Very carefully remove the
inverted watch glass taking care not to disturb the sublimate.
8. Observe the crystalline structure of the sublimate. Compare with the original.
9. Determine the weight of the sublimate and calculate the percentage of the pure crystals
recovered from the impure sample, using the formula
 weight of recovered crystals (sublimate)
%recovery = ------------------------------------------- x 100
weight of original crystal

10. Keep the crystals in a small vial for future use. Label properly.

Data and Results Solution:

Weight of empty watch glass, g

Weight of crystals, g

Weight of empty watch glass +

sublimate, in grams
Weight of sublimate, g

Weight of sublimate, g

% Recovery

Conclusion
Date Performed: ____________________ Score:_______

Learning Activity No. 5

PURIFICATION BY DISTILLATION

Specific Learning Objectives:

At the end of the experiment the students can:

1. purify impure liquid organic compounds through distillation.
2. discuss the concepts involved in distillation.

Time Allotment: 3 hours

Learning Resources

Chemicals/ Reagents:
Solutions of the following:
ethanol and water

Apparatus: quick fit apparatus for simple distillation, iron stand, Bunsen burner, iron clamps,
graduated cylinder 10mL, rubber tubing, wire gauze, iron ring, Erlenmeyer flask,

Learning Strategies:

Distillation involves the change of a liquid to the vapor state by heating in one vessel and
condensing the vapor back to the liquid state in another vessel. This method is usually employed
at atmospheric pressure for the purification of liquid organic compounds which do not decompose
at their boiling points.

If the impurities are not volatile, simple distillation is used. If the compound decomposed when
boiled at atmospheric pressure, the pressure within the distillation set-up is lowered by means of
a vacuum pump, thus lowering the boiling temperature. This method is known as vacuum
distillation or distillation under reduced pressure.

If an organic liquid is immiscible in water and has an appreciable vapor pressure near 1000C.., it
may be purified at a temperature far below its boiling point by steam distillation.

Learning Content

1. Arrange the assembly for the simple distillation.

2. Obtain 25 mL of methanol and water solution and place the liquid in the distilling flask
and add small boiling stones or glass chips.
3. Adjust the thermometer so that mercury bulb is just below the opening of the side
tube.
4. Inspect all connections for possible leakage.
5. Adjust the receiver reaching to about two-thirds of its depth.
6. Heat the flask slowly by means of a small flame.
7. Note the temperature where the first drop distills over. Adjust the heating to about a
drop every 5 seconds or 1 mL in 23 minutes.
8. Record the boiling point for each ml of the distillate collected.
 9. Change the receiver after each 3 mL fraction. Save all fractions to fraction C and
label properly.
10. Submit to the instructor.
11. Plot a graph of boiling point versus volume of distillate.

Set-up

Data and Results:

Fraction Boiling point in 0C

Fraction A
1st drop
1 ml
2 ml
3 ml
Fraction B
4 ml
5 ml
6 ml
Fraction C
7 ml
8 ml
9 ml
10 last drop
CONCLUSION:
Learning Evaluation

ASSIGNMENT: Use a separate sheet of bond paper.

Draw and label the following distillation set-ups

a. simple distillation
b. steam distillation
c. vacuum distillation