POLITÉCNICO COLOMBIANO JAIME ISAZA CADAVID

FACULTAD DE CIENCIAS BÁSICAS, SOCIALES Y HUMANAS

PROGRAM: Tecnología en Química Industrial y de
Laboratorio
COURSE: Organic Chemistry
PRACTICE NAME: Physical Properties: Boiling Point of Organic
Compounds
PRACTICE TYPE: Virtual

SOFTWARE AMRITA (ONLINE LABS)

Boiling point of Organic compound

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 Boiling Point of an Organic Compound

1. Objective
Our objective is to determine the boiling point of an organic compound.

2. The 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?

A. 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.
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.

B. 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.
C. 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.

D. 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

3. Learning Outcomes
 Students understand the term boiling point from this experiment.
 Students understand the procedure to determine the boiling point in other organic liquids.
 Students understand that the boiling point of a liquid is a constant.

4. Materials Required
5. The Procedure

Real Lab Procedure

 First fill two-thirds of the small test tube with the given liquid whose boiling point needs to be
determined.
 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.
 Fill half of the beaker with Con. sulphuric acid and place it over a wire gauze placed over a
tripod stand.
 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.
 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.
 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.
 Place the capillary tube in the test tube containing the given liquid so that the sealed part of
it stands in the liquid.
 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.
 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.
 Note the temperature (t1) when continuous stream of bubbles starts coming out.
 Remove from the flame and note the temperature (t 2) when the evolution of bubbles from
the end of the capillary tube just stops.
 The mean of these two temperatures gives the boiling point of the liquid.
 Allow the temperature to fall by 10 oC and repeat the heating and again note the boiling
point.

Simulator Procedure (as performed through the Online Labs)

 You can select the compound from the ‘Select the unknown compound’ drop down list.
 To start the experiment, click on the ‘Start’ button.
 The temperature begins to rise.
 Note the temperature ‘t1’ at which a continuous stream of air bubbles appear from the end
of the capillary tube.
 Now turn off the burner by clicking on the ‘Knob’ of the burner.
 Note the temperature ‘t2’ at which the air bubbles completely disappear.
 Enter the values in the respective text boxes.
 The boiling point of the compound is shown in the text box.
 You can select the actual compound from the ‘Select the actual compound’ drop down list.
 You can verify your result by clicking on the ‘Show chart’ button.
 To redo the experiment, click on the ‘Reset’ button.
6. Observations
Record your observations in the table given below.
Note the temperature when;
Boiling Point of the given
The evolution of gas bubbles just organic liquid (t1 + t2 / 2
Rapid and continuous evolution stops t2 (0C) (after removing from
of gas bubbles occurs t1(0C) (oC)
the flame)

7. Inference
The boiling point of the given organic liquid = ... oC.

8. Precautions
 If on placing the sealed capillary tube in the test tube, the liquid is seen rising in the capillary
tube, it indicates that the capillary tube is not properly sealed. Reject this capillary tube and
use a new one.
 The seal point of the capillary tube should be well within the liquid.
 The acid bath must be heated very slowly and the acid is stirred to ensure uniform heating.

9. Important Words
 Characterise (verb), to describe the defining qualities of an object a particular
Characteristic (noun), defining quality
Characterisation (noun): a description of the defining qualities of an object.
 Compound: a substance composed of two or more elements.
 Conversely: to add the opposite or reverse idea.
something that demonstrates a relationship of similarity to the
 Derivative:
original.
the act or manner of spreading something. (root word- Dis- =
 Dispersion:
apart. Examples; disappear, disgrace, disappoint).
that which gives an indication, an idea of the relative value or
 Indicator:
quality of something.
compounds consisting of ionic bonds where the attraction of
oppositely charged ions forms the bond. In fact, a pure ‘ionic
compound’ is not possible: some covalent bonding is always
 Ionic compounds:
present. A bond is termed ‘ionic’ when the electrical attraction is
greater than the covalent attraction. High melting and boiling
points are characteristic of ionic compounds.
compounds that have the same molecular formula but differ in
 Isomers:
their arrangement and properties.
motion or movement. Kinetic energy is the energy of a molecule
 Kinetic: in movement (see potential energy).
 Polarity: having two oppositely charged poles.
 Properties: the characteristic qualities of a something.
 Proportion (noun), the relative size or quantity of the parts.
Proportional
(adjective):
 Sufficient: having or being enough.
a Dutch physicist who won the 1910 Nobel Prize for his work on
 Van der Waals: the behaviour of gases. His name was given to certain weak
electrostatic bonds between atoms and molecules.
 Velocity: the rate of speed or movement.
 Volatile (adjective), describes a substance that evaporates at normal temperatures.
Volatility (noun):

10. Resources
Books:
 Laboratory Manual Chemistry for class XI - Published by NCERT

Websites:
 www.masterorganicchemistry.com/2010/10/25/3-trends-that-affect-boiling-points/
 faculty.coloradomtn.edu/jeschofnig/class/class_jeschof/ch1-lb10.htm
 www.youtube.com/watch
 www.youtube.com/watch

ANNEXED

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