School of Che-Chm

Results and Discussion of Experiments 1 to 5

Experiment No. 1
MELTING POINT AND
BOILING POINT

MELTING POINT
The temperature at which the solid and the
liquid phases are in equilibrium at a pressure
of 1 atm.
The temperature at which thermal agitation
overcome a certain degree of attraction
between the molecules thereby changing it
from solid to liquid.
Melting point range is the range between:
The temperature at which the sample begins
to liquefy
The temperature at which it is completely
liquid, called liquefaction point.
Importance of melting point determination:
1. To check accuracy of the thermometer.
2. To know the purity of the compound
Melting point range 2oC - pure substance
Melting point range 5oC - impure substance
Types of Intermolecular Attraction:
1.

Van der waals weakest

Induced fluctuating charges due to
electronic distribution within the molecules
Residual attraction due to the motion of
molecules which, produces electrical fields
causing the molecules that are near and
properly oriented to attract each other. All
organic compounds exhibit it.
Dipole- dipole forces
Dipole induced dipole
Ion induced dipole
London dispersion forces
2. Ion dipole forces
3. Hydrogen bonding
Residual attraction exhibited by hydrogen
when it is bonded to an electronegative atom
or group such as F, O and N. The mechanism is
believed to be electrostatic in nature.
Example:
alcohol, ROH
carboxylic acid, RCOOH
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CHM142L (Organic Chemistry 1 Laboratory)

Factors Affecting MP:

A. Intermolecular Forces of Attraction
The
greater
the
forces
of
attraction between molecules, the higher are
the MP of the compound.
B. Geometric Isomer
The trans isomer has higher MP
than the cis isomer due to symmetry.
C. Purity
Pure compound has narrow MP range
than impure. Also impure compounds have
higher MP than impure.

BOILING POINT
The temperature at which the vapor
pressure of the liquid is equal to the
external pressure at the surface of the
liquid.
The temperature at which the liquid is in
equilibrium with its vapor phase at that
pressure.
The temperature at which thermal agitation
is able to overcome a certain degree of
attraction between the molecules thereby
changing it from liquid to vapor.
Factors Affecting MP:
A. Intermolecular Forces of Attraction
The
greater
the
forces
of
attraction between molecules, the higher are
the MP of the compound.
B. Molecular Weight
BP increases with increasing number
of carbon.
For molecules of the same molecular
weight, the greater the polarity the higher is
the BP.
C. Branching
Highly branched molecules tend to
have higher BP.

Page 1 of 5

School of Che-Chm
Results and Discussion of Experiments 1 to 5

Experiment No. 2
RECRYSTALLIZATION

RECRYSTALLIZATION
One of the processes of purifying impure
solids. It involves dissolving the compound in a
desirable solvent, crystallizing it again as solid
free from impurities.
The simplest and the most widely used
operation for purifying organic solids.
Properties of a solvent from recrystallization:
1. It dissolves compound sparingly at room
temperature
2. It
dissolves
compound
at
elevated
temperature
3. Have different solubilities for the compound
and impurities
4. Have a boiling point below the melting point of
the compound
5. Have a relatively low boiling point (60-100oC)
6. It gives no chemical reaction with the
compound
7. It must be volatile enough to be easily
separated from the purified sample thru
evaporation
8. Be relatively inexpensive
Rapid filtration is done by:
Buchner funnel by giving difference in inside
and outside pressure (1 atm) of the funnel.
Pout > Pin ; thus pushes filtrate to the flask
Precaution: filter paper is large enough to
cover only holes of funnel

Note: When a partial vacuum is created in the flask

by vacuum pump or water aspirator, liquid is forced
through the filter paper by the unbalanced external
pressure. A filter trap placed between the flask and
the aspirator helps prevent water from backing up
into the flask when the water pressure changes. The
filter trap can be a thick-walled Pyrex jar, wrapped
with transparent plastic tape to reduce the chance
of injury in case of implosion.

Stemless funnel using fluted filter paper to

allow more passage of filtrate.
Formation of crystal maybe:
Spontaneous crystal appear out on cooling or
cooling with stirring

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CHM142L (Organic Chemistry 1 Laboratory)

Non-spontaneous requires outside force

for the recrystallization of the sample.
Methods used to induce formation of
crystals may be:
Seeding process adding fine
crystals to the cold solution
Scratching the sides of the
container. The rough sides serve as
crystal nuclei.
Solvent pair is a mixture of two solvents that
possesses properties of a solvent good
for recrystallization as pair. One of the
solvent pair dissolves the compound in
the cold or hot while the other one does
not dissolve the solute at cold or hot.
Based on solubility test, the following solvents are
suitable for recrystallization:
1. naphthalene - water and ethanol
2. acetanilide - water
3. acetamide - benzene
4. sucrose - ethanol
5. benzoic acid - water
6. aspirin - benzene
Problem Solving
How many grams of acetanilide will be recovered by
recrystallization of 10 g of impure compound using
300 ml H2O. How many ml of water is needed to
prepare a saturated solution of 10 grams acetanilide
with traces of impurities.
Solubility of acetanilide at room temp 0.54g/100 ml
H 2O
Solubility of acetanilide at 90oC 4.3 g/100 ml H2O

Experiment No. 3
SIMPLE AND STEAM
DISTILLATION

DISTILLATION
A method of purification and separation of
mixtures that involves the conversion of
sought-for to the vapor state and
condensation of the vapor to the liquid state.
This is carried out because of the difference
in the boiling points of the mixture.
Page 2 of 5

School of Che-Chm
Results and Discussion of Experiments 1 to 5

CHM142L (Organic Chemistry 1 Laboratory)

Distilland the mixture being distilled usually placed in

the distilling flask.
Distillate the resulting liquid in distillation collected
in a receiver
Type of Distillation Set-up:
1. Open Distillation - set-up open
atmosphere, for non-flammable
non-volatile components.
2. Close Distillation - set up closed
atmosphere, for flammable
volatile components.

to
and
to
and

Types of Condenser:
1. Water Condenser - used for components
whose boiling point < 150oC.
2. Air Condenser used for components whose
boiling point > 150oC in order to avoid breakage
of apparatus due to the big difference in
temperature between water and components
of mixture.
Types of Distillation:
1. Simple Distillation involves only one single
vaporization-condensation cycle.
- most useful for purifying a liquid that
contains either non volatile impurities or
small amounts of higher-or-lower boiling
point impurities.
- components with 20o difference in boiling
point.
a. macromethod - volume > 20 ml
b. semi-micro method - volume < 20 ml
2. Fractional Distillation allows for several
vaporization-condensation cycles.
- It can be used to separate liquids with
comparable volatilities and to purify
liquids containing larger amounts of
volatile impurities.
- components with boiling point difference <
20o.
3. Vacuum Distillation is carried out under
reduced pressure, which reduces the
temperature of the distillation.
- It is used to purify high-boilong liquids
and liquids that decomposed when distilled
at atmospheric pressure.
4. Steam Distillation involves distillation of a
mixture of two (or more) immiscible
liquids where one of the liquid is water.

Two Types:
a. Internal steam distillation carried
out by boiling a mixture of
water and an organic material in
a distillation apparatus causing
vaporized water (steam) and
organic liquid to distill into a
receiver.
b. External steam distillation is carried
out
by
passing
externally
generated steam into a boiling
flask containing the organic
material. The vaporized organic
liquid is carried over into a
receiver with the condensed
steam.
Properties of organic compounds to be
separated by steam distillation:
1. must have an appreciable vapor
pressure (at least 5 mm Hg at 90oC)
2. must be water-insoluble
3. must have high boiling point
4. must be unstable at their boiling
point
5. must not react with steam
Steam distillation depends on the fact that
when 2 or more completely immiscible or slightly
miscible liquid are mixed, the vapor pressure of the
mixture is the sum of the vapor pressure of each of
the pure component. Thus if component A is heated
together with water, both will exert their own vapor
pressure independently of the other.
PT = PA + Pwater
When a liquid mixture is distilled it boils
when the sum of the vapor pressure is equal to the
atmospheric pressure. The temperature at which the
mixture distills will therefore be lower than the
boiling point of any of the pure components.
Assuming that gas laws are applicable, the
component of the vapor and of the distillate may be
easily calculated since the partial vapor pressure of
each component is directly proportional to the
number of moles of each component of the vapor.
For 2 compounds, steam and compound A,
nsteam/nA = Psteam/PA

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School of Che-Chm
Results and Discussion of Experiments 1 to 5

CHM142L (Organic Chemistry 1 Laboratory)

Since n = weight/MW, then,

(weight/MW)steam
(weight/MW)A
weightA
weightsteam

Psteam
PA

(P x MW)A
(P x 18)steam

The higher the vapor pressure PA of the

substance of MWA, the less steam required distilling a
given weight, WA of the substance A.

dependent upon the nature of the compounds

and the solvent.
Compounds are separated by adsorption
chromatography based upon differential
attachment of molecules to the adsorbent
and the polarity of the solvent used for
separation.
Notes:

Problem Solving
Methylaniline is steam distilled at 99oC (vapor pressure
of water at 99oC = 733 mm Hg). What mole fraction of
methylaniline is present with water in the steam
distillate? Calculate the weight ratio at which the two
compounds distill.

Experiment No. 4
CHROMATOGRAPHY
Chromatography
A method of analysis in which a mixture is
partially/completely
separated
into
its
components
according
to
the
relative
attraction of the components for a stationary
and mobile phase.

Paper

chromatography is a form of plane

chromatography in which a filter paper/cellulose
is used as the stationary phase & a liquid solvent
as the mobile phase.

Thin Layer Chromatography (TLC) is the separation

of moderately volatile substances based upon
differential adsorption on an inert solid
(stationary phase) immersed in an organic solvent
mixture (mobile phase)

Polar compounds are strongly attracted to and

held by a polar solvent.
Non polar compounds are weakly held. When polar
solvent is passed through the adsorbent, non polar
compounds are released easily, but polar
compounds are retained.
When moderately polar solvent is passed through
the adsorbent, both non polar and polar compounds
are released but the non polar compounds move
faster because there is still an attraction between
the polar compounds and the polar adsorbent.
Non polar compounds move faster than polar
compounds for TLC on silica gel or alumina.

Types of Paper Chromatography:

1. Ascending Paper Chromatography the
mobile
phase
flows
upward
the
stationary phase
2. Descending Paper Chromatography the
mobile phase is added to the top of the
stationary phase & descending through
the paper
Rate of flow, Rf is a convenient way of describing
the relative ease with which various substances
move along the paper.
- is also called rate factor of retardation
rate.
Rf = distance traveled by spot/ distance traveled
by solvent
Note; Rf values on silica gel or alumina are decreased
by decreasing the polarity of the solvent & increased
by increasing the solvent polarity.

Principles:
The components are distributed between the
stationary phase (usually silica gel or alumina)
and the solvent depending on the polarities of
the compound and the solvent.
The compounds are carried up the plate
(ascending chromatography) at a rate

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School of Che-Chm
Results and Discussion of Experiments 1 to 5

Experiment No. 5
EXTRACTION

Extraction
The method of separating an organic
substance from an aqueous solution by adding
to the solution a water-immiscible liquid in
which the organic substances is dissolved.
Properties of Solvent used for extraction:
1. Water immiscible
2. Do not react with water or the substance
3. Capable of dissolving the substance to be
extracted readily, which means that it, has a
favorable distribution coefficient.
4. Very volatile
The common solvent in extraction is diethyl ether
because it is:
1. Water immiscible
2. Inert to most organic compounds
3. Very volatile

CHM142L (Organic Chemistry 1 Laboratory)

2. A solution is made by dissolving 35 mg

caffeine in 7.5 mL of water. How many
milligrams of caffeine will be extracted
using:
a. one portion of 15 mL of methylene
chloride
b. two portion of 7.5 mL of methylene
chloride
c. three portion of 5 mL of methylene
chloride
Salting-out effect
The solubility of organic substance in water
is markedly affected by the presence of dissolved
inorganic salts. The addition of salt causes the
solubility of the solvent and organic solid in water to
decrease. This phenomenon of salting-out effect
commonly occurs with salts having ions of small radius
and concentrated charge.

Note: The distribution coefficient K, of adipic acid in

ether-water layer is 0.43.

The distribution of the substance between two

immiscible phases is the bases of extraction. During
extraction the organic compound will distribute itself
between the two immiscible liquids. At a given
temperature, the ratio of the equilibrium concentration
of a substance distributed between the two immiscible
solvents is constant and is known as the partition
coefficient.
Mathematically,
K = CA/CB
where: K = partition coefficient
CA = concentration of compound in
organic solvent in g/mL
CB = concentration of compound in
water in g/mL
Note: The larger the K, the more solute will be transferred to
the ether layer and the fewer portions of ether will be
required for essentially complete removal of the solute.

Problem Solving:
1. Approximately 1.0 g of caffeine will dissolve in
28 mL of methylene chloride and in 46 mL of
water. Calculate the distribution coefficient
of caffeine in this solvent.

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