Republic of the Philippines

University of Northern Philippines

Tamag, Vigan City
2700, Ilocos Sur

BOILING POINT OF ORGANIC COMPOUNDS

I. Objective:
To determine the boiling point of an organic compound.

II. Theory:
What is the importance of knowing the boiling point of organic compounds?
The boiling point of organic compounds can give important information about their physical
properties and structural characteristics. Boiling point helps identify and characterise a
compound. A liquid boils when its vapour pressure is equal to the atmospheric pressure.
Vapour pressure is determined by the kinetic energy of a molecule.

Kinetic energy depends on the temperature, mass and velocity of a molecule. When the
temperature increases, the average kinetic energy of particles also increases. When the
temperature reaches the boiling point, the average kinetic energy becomes sufficient to
overcome the force of attraction between the liquid particles. As the force of attraction
decreases, the molecules in the liquid state escape from the surface and turn into gas.

The boiling point of a liquid varies with the surrounding atmospheric pressure. A liquid at a
higher pressure has a higher boiling point than when that liquid is at lower atmospheric
pressure.

The normal boiling point of a compound is an indicator of the volatility of that compound.
The higher the boiling point, the less volatile is the compound. Conversely, the lower the
boiling point, the more highly volatile is the compound. At a given temperature, if a
compound’s normal boiling point is lower, then that compound will generally exist as a gas
at atmospheric pressure. If the boiling point of the compound is higher, it then exists as a
liquid or a solid.

What are the general trends that affect the boiling point?
1. Strength of intermolecular forces
The relative strength of intermolecular forces such as ionic, hydrogen bonding, dipole-dipole
interaction and Vander Waals dispersion force affects the boiling point of a compound. The
influence of these forces depends on the functional group present. We can explain the
effect of these forces on the boiling point of compounds with the help of some examples.

Consider butane and its three derivatives such as diethyl ether, n- butanol and sodium n-
butoxide.

General Chemistry Organic Laboratory

April Ellen B. Baccay, BSChem Eng, RChT
n-butane (C4H10) contains no polar functional group. The only attraction between the
butane molecules is weak Vander Waals dispersion forces. The result is that butane boils at
a temperature at which water freezes, and is much lower than diethyl ether. In the case of
diethyl ether, the molecules are held together by dipole-dipole interaction which arises due
to the polarized C-O bond. Its boiling point is 35oC. Compare its boiling point with that of n-
butanol. The boiling point of n-butanol is 117oC. The greatly increased boiling point is due to
the fact that butanol contains hydroxyl group, which is capable of hydrogen bonding. But
the boiling point of sodium butoxide is higher than that of butanol because the attractive
force in sodium butoxide is very strong ionic bond.

The intermolecular forces go in the order Ionic > Hydrogen Bonding > Dipole-Dipole > Van
der Waals dispersion force.

2. Length of carbon-carbon chain

As the number of carbon atoms increases or the length of carbon-carbon chain increases,
the boiling point also increases. This is because the force of attraction between the
molecules increases as the molecule gets longer and has more electrons. It takes more
energy to overcome the force of attraction, and so the boiling point rises.

General Chemistry Organic Laboratory

April Ellen B. Baccay, BSChem Eng, RChT
 3. Branching decreases the boiling point
As the length of carbon chain increases, the surface area of the compound will also increase.
Van der Waals dispersion force is proportional to the surface area. So the increase of
surface area increases the ability of individual molecules to attract each other. Branching in
molecules decreases the surface area thereby decreasing the attractive force between
individual molecules. As a result, the boiling point decreases.

Consider the boiling point of n-pentane and neo-pentane (2,2-dimethyl propane). These are
isomers having the same molecular formula (C5H12), but differ in their structures.

The boiling point of neopentane is much lower than that of n-pentane.

4. Polarity
Polarity of the molecule determines the force of attraction between the molecules in the
liquid state. In polar compounds, the positive end of one molecule is attracted by the
negative end of another molecule. That means polar molecules are attracted by opposite
charge effect. The polarity of a molecule is determined by its functional group. The greater
the polarity, the higher is the boiling point.

Boiling point of some common organic compounds

Compound Boiling Point (oC) Compound Boiling Point (oC)
Benzyl Alcohol 205 Ethyl Benzoate 213
Glycerol 290 Methyl Salicylate 223
Ethylene Glycol 197 Nitrobenzene 211
Phenol 182 Aniline 184
o-Cresol 191 o-Toluidine 200
Benzaldehyde 178 Chlorobenzene 132
Acetophenone 202 Bromobenzene 156
Phenyl Acetate 196 Benzoyl Chloride 197

III. Materials Required:

General Chemistry Organic Laboratory

April Ellen B. Baccay, BSChem Eng, RChT
 IV. Procedure:

Real Lab Procedure

1. First fill two-thirds of the small test tube with the given liquid whose boiling point
needs to be determined.
2. Fix this test tube to the thermometer with a rubber band in such a way that the
bottom of the tube is at the middle of the thermometer bulb. The rubber band
should be fixed near the mouth of the tube so that it remains outside the acid bath.
3. Fill half of the beaker with Con. sulphuric acid and place it over a wire gauze placed
over a tripod stand.
4. Clamp the thermometer carrying the test tube to an iron stand through a cork.
Lower the thermometer along with the tube into the acid bath.
5. Adjust the thermometer so its bulb is well under the acid and the open end of the
tube with the rubber band is sufficiently outside the acid bath.
6. Take the capillary tube and seal at it about 1 cm from one end by heating it in flame
and giving it a slight twist.
7. Place the capillary tube in the test tube containing the given liquid so that the sealed
part of it stands in the liquid.
8. Start heating the acid bath slowly and stir the bath gently. Keep an eye on the liquid
and the test tube and also on the thread of the mercury in the thermometer.
9. At first a bubble or two will be seen escaping at the end of the capillary tube dipped
in the liquid, but soon a rapid and continuous stream of air bubbles escapes from it.
At this stage the vapour pressure of the liquid just exceeds the atmospheric
pressure.

General Chemistry Organic Laboratory

April Ellen B. Baccay, BSChem Eng, RChT
 10. Note the temperature (t1) when continuous stream of bubbles starts coming out.
11. Remove from the flame and note the temperature (t2) when the evolution of
bubbles from the end of the capillary tube just stops.
12. The mean of these two temperatures gives the boiling point of the liquid.
13. Allow the temperature to fall by 10oC and repeat the heating and again note the
boiling point.

Simulator Procedure (as performed through the Online Labs)

Link: http://amrita.olabs.edu.in/?sub=73&brch=7&sim=111&cnt=4

1. You can select the compound from the ‘Select the unknown compound’ drop down
list.
2. To start the experiment, click on the ‘Start’ button.
3. The temperature begins to rise.
4. Note the temperature ‘t1’ at which a continuous stream of air bubbles appear from
the end of the capillary tube.
5. Now turn off the burner by clicking on the ‘Knob’ of the burner.
6. Note the temperature ‘t2’ at which the air bubbles completely disappear.
7. Enter the values in the respective text boxes.
8. The boiling point of the compound is shown in the text box.
9. You can select the actual compound from the ‘Select the actual compound’ drop
down list.
10. You can verify your result by clicking on the ‘Show chart’ button.
11. To redo the experiment, click on the ‘Reset’ button.

V. Data and Results

JOHN MICHAEL INES
BSCRIM 2K
Note the temperature when; Name of
Boiling Point of Compound
Rapid and The evolution of
continuous gas bubbles just the given
evolution of gas stops t2 (0C) organic liquid
bubbles occurs (after removing (t1 + t2 / 2 (oC)
t1(0C) from the flame)
Compound 1 207 203 205 Benzyl Alcohol
Compound 2 292 288 290 Glycerol
Compound 3 195 199 197 Ethylene Glycol
Compound 4 184 180 182 Phenol
Compound 5 180 176 178 Benzaldehyde
Compound 6 205 199 202 Acetophenone
Compound 7 213 209 211 Nitrobenzene

General Chemistry Organic Laboratory

April Ellen B. Baccay, BSChem Eng, RChT
 Compound 8 186 182 184 Aniline
Compound 9 199 193 196 Phemyl acetate
Compound 10 134 130 132 Cholorobenzene
Compound 11 255 221 223 Methyl benzoate
Compound 12 193 189 191 o - Cresol
Compound 13 215 211 213 Ethyl benzoate
Compound 14 203 197 200 o - Toluidine
Compound 15 158 154 156 Bromobenzene

Precautions:

● If the liquid rises the capillary tube after.is placed in the test tube.it is sealed .it means that
the camillary tube is not scaled properly.an replace it with a fresh one.
● The capillary tube's seal points should be well within the liquid

● The guarantee homogeneous heating ,the acid bath must be heated slowly and stirring is
required.

VI. Conclusion
First, select compound ,then click start,and the temperature will begin to rise .rise and
appear to be continuous streams of air bubbies the burner must be turned off and the
temperature t2 must be reached before the air bubbles fully dissipate.

VII. Documentation

General Chemistry Organic Laboratory

April Ellen B. Baccay, BSChem Eng, RChT