CM134-1L: ORGANIC CHEMISTRY 2 LABORATORY

1ST Quarter SY 2019-2020

MELTING POINT AND BOILING POINT OF ORGANIC COMPOUNDS

ORTEGA, MARY ALYSSA T. – GROUP 3
AUGUST 22, 2019

Introduction

There are different factors that can affect the properties of various organic compounds. Structural
theory states that the chemical structure of organic compounds greatly influenced these properties. These
properties can be classified as physical and chemical properties. Physical properties are defined as both
extensive and intensive properties that can be measured without changing the substance’s chemical identity
(e.g. boiling point, melting points, freezing points, solubility in polar and nonpolar solvents). On the other
hand, chemical properties are characteristic of a substance that becomes evident during a chemical reaction
and can be established only by changing a substance’s chemical identity (e.g. combustibility, halogenation,
flammability, etc.). In this experiment, we will be only focusing on two examples of physical property of
different organic compounds—melting point and boiling point.

The melting point of a substance is the temperature at which the material changes from a solid to a
liquid state. It is an important physical property of a compound. The melting point can be used to identify a
substance and as an indication of its purity. The melting point of solid is defined as the temperature at which
the solid exists in equilibrium with its liquid under an external pressure of one atmosphere. An energy is
needed to break the intermolecular forces that bind organic molecules from its solid state to a liquid state.
There are different factors that can affect the melting point of an organic compound such as the size of the
molecule and force attraction between molecules. Intermolecular forces between molecules is one of the
main subjects thus determining this is the one of the main objectives of this experiment. The force of attraction
between the molecules affects the melting point of a compound. Stronger intermolecular interactions result
in higher melting points. Ionic compounds usually have high melting points because the electrostatic forces
holding the ions (ion-ion interaction) are much stronger. In organic compounds the presence of polarity, or
especially hydrogen bonding, generally leads to higher melting point.

The boiling point of a liquid is determined by heating the liquid as it reaches a certain temperature
wherein the vapor pressure is enough to form its first bubbles in the liquid. This type of measurement of a
temperature of a pure organic liquid is one of its characteristic physical properties. Boiling point helps identify
and characterize a compound. A liquid boils when its vapor pressure is equal to the atmospheric pressure.
The vapor pressure can be determined by the kinetic energy of a molecule wherein is dependent with
temperature. When the temperature increases, the average kinetic energy of particles also increases. 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 and the lower the boiling point, the more volatile the compound is. Similar to melting point, the
boiling points of substances often reflects the strength of the intermolecular forces occurring between the
molecules. There are also other factors that can affect the boiling point of an organic compound—the length
of carbon-carbon chain: that means as the number of carbon atoms increases or the length of carbon-carbon
chain increases, the boiling point also increases. Polarity of the molecule determines the force of attraction
between the molecules in the liquid state. The polarity of a molecule is determined by its functional group.
The greater the polarity, the higher is the boiling point.

The experiment involves the two physical properties: Melting Point and Boiling Point of Organic
Compounds. The purpose of this experiment was to determine the effect of intermolecular forces of attraction
and geometric isomerism on the melting point of compounds and the branching on the boiling point of organic
compounds; and the effect of purity on the melting point range of organic compounds. The two properties
were determined and compared to the other compounds.
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Materials and Methods

The experiment was divided into two parts—melting point of certain solids and the boiling point of
liquids. For the determination of melting point, the apparatus used are Thomas-Hoover Melting Point
Apparatus, Thiele tube, Hot plate, Micro test tubes, and Capillary tubes. There are eight solid test compounds
that are used for determining the melting point namely Maleic Acid, Salicylic Acid, Benzoic Acid, Fumaric
Acid, Urea, Impure Urea, Naphthalene and Benzoin. On the other hand, for the determination of boiling
points, 8 liquid test compounds were utilized: n-Butanol, 2-Butanone, n-Hexane, n-Pentane, Propanoic acid,
n-butyl alcohol, sec-butyl, and tert-butyl alcohol. The Glycerol was used for the oil bath on the determination
of the boiling point range.

The capillary tubes are used for both parts of the experiment, to gather liquid and solid samples for
melting and boiling points experiment. The first procedure of the experiment was done by sealing the end of
the capillary tube by direct heat using the Bunsen burner. The sealed capillary tubes are then used as sample
holders by tapping it to the solid samples and dropping it inside the glass tubing in order to move the sample
to the bottom. These sealed tubes are used for the melting part of the experiment. After gathering the samples
of 8 test compounds, these capillary tubes were placed on Thomas Hoover Apparatus for determining the
temperature at which the samples start to melt (T1) and completely melted (T2) or is in its liquid phase. This
procedure is repeated to all solid samples and their temperatures are recorded.

The second part of this experiment is the determination of boiling point of various test compounds.
This requires more time compared to the first part of the experiment. The thiele tube was filled with a just
amount of Glycerol and was attached on the iron clamp connected to the iron stand and placed right above
the Bunsen burner. The next step was to set up the capillary tube is inverted and is placed inside the micro
test tube with the liquid sample. It was made sure that the capillary tube is immersed inside the test tube. The
test tube was secured beside the thermometer through a masking tape. It was then attached to the iron clamp
in which the ends of the thermometer and the test tube are immersed on the thiele tube with glycerol. The oil
bath was heated using the Bunsen burner. The samples were observed carefully until bubbles came out of
the capillary tube and its first temperature (T1) is recorded. The set-up was removed from the heat to let the
oil to cool down. The sample was reheated and observed until the liquid sample inside the capillary tube
came out at a certain temperature (T2). These two temperatures indicate the boiling point range of a particular
organic compound.

Results and Discussion

The results obtained from experiment in determining the melting point and boiling point was then
gathered and recorded on the data. The data obtained from the melting point of the solid organic compounds
was provided and separated into three parts that indicate the effects of different factors in the compound’s
melting point range.

Table 1. Structural Effect of Intermolecular Forces of Attraction

COMPOUND T1 (°C) T2 (°C) MELTING POINT
Benzoic Acid 93.2 162 127.6
Benzoin 112 151 131.5
Naphthalene 68.2 122.8 95.5
Salicylic Acid 152.8 184 168.4
Urea 116.6 158 137.3

The gathered data T1 and T2 were used to get the average that serve as the melting point of the
compound. Based on the data above, the Salicylic acid has the highest melting point, followed by Urea,
Benzoin, Benzoic Acid and the lowest melting point is Naphthalene. Salicylic Acid having the highest melting
point means that this compound has the greatest intermolecular force among all. On the other hand,
Naphthalene having the lowest melting point means it has the lease intermolecular force among the other
solid compounds.

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Table 2. Structural Effect on Geometric Isomers or Substituent
COMPOUND T1 (°C) T2 (°C) MELTING POINT
Maleic Acid 102.4 174 138.2
Fumaric Acid 272 302 287

The data above shows the large difference of their melting points between the two compounds.
Fumaric acid has a higher value of melting point rather than the maleic acid despite of its similar molecular
weight. This is because these compounds have different intermolecular forces. The Geometric Isomerism
occurs when there is a restricted rotation of molecules. Maleic Acid is a cis-isomer while Fumaric Acid is a
trans-isomer. It can be said that the position of their substituent affects its melting point. Cis-isomer is wherein
the identical atoms are located on the same side of a bond while trans-isomer is that the identical atoms are
on the opposite sides of the bond. A trans-isomer has a higher melting point meaning it needs more energy
to break the intermolecular forces than cis-isomers.

Table 3. Effect of Purity on Melting Point Range

COMPOUND T1 (°C) T2 (°C) MELTING POINT
Pure Urea 116.6 158 137.3
Impure Urea 99.7 149.1 124.4

The data placed on the Pure Urea is the same as the value of Urea in table 1. The data obtained
provides a large range between the two gathered temperatures. The pure compound has 41.4°C interval of
values while the impure compound has 49.4°C. Impure Urea has a larger range of melting point producing a
lower melting point than Pure Urea. This is because impurities affect the quality, structure of the organic
compound and the presence of impurities decreases the number of water molecules available to be
vaporized.

On the other hand, the data for the determination of the boiling point of the liquid compounds were
gathered and were divided into two parts. Similar with the method for melting point, the average of two
temperatures served as the boiling point of the liquid compound.

Table 4. Structural Effect of Intermolecular Forces of Attraction

COMPOUND T1 (°C) T2 (°C) BOILING POINT
n-Butanol 112 126 119
2-Butanone 67 92 79.5
n-Pentane 33 41 37
Propanoic Acid 136 148 142
n-Hexane 62 84 73

Propanoic Acid having the highest boiling point because it is polar and occurred a hydrogen bonding
which is one of the strongest intermolecular forces. The greater its intermolecular force, the higher its melting
point because it is harder to break the binding compounds. However, the n-Pentane has the lowest boiling
point since there are no hydrogen bond present.

Table 5. Structural Effect of Branching

COMPOUND T1 (°C) T2 (°C) BOILING POINT
n-butyl alcohol 112 126 119
sec-butyl alcohol 98 110 104
tert-butyl alcohol 79 95 87

These compounds are classified as alcohols which contain hydrogen atoms and tend to have strong
hydrogen bonding which results to have a large actual boiling point. Thus, n-butyl has the strongest
intermolecular force and greater number of carbon atoms, followed by sec-butyl and tert-butyl alcohol
resulting to n-butyl having the highest boiling point followed by sec-butyl then tert-butyl alcohol.

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 To summarize the data gathered for both parts of the experiment. Figure 1 is a bar graph that
summarized the experimental value of the melting point of the solid compounds while Figure 2 provides the
values for the boiling point of the liquid compounds.

Benzoic Acid Benzoin Naphthalene

Salicylic Acid Urea Maleic Acid

350

300

250

200

150

100

50

Figure 1. Summarized values for Melting Point of Solid Compounds

n-Butanol 2-Butanone n-Pentane

Propanoic Acid n-Hexane n-butyl alcohol
sec-butyl alcohol tert-butyl alcohol

160
140
120
100
80
60
40
20
0

Figure 2. Summarized values for Boiling Point of Liquid Compounds

Conclusions

In this experiment, the boiling point and melting point were determined using the heating of glycerol
as oil bath and Thomas-Hoover Melting point apparatus respectively. Their data were compared and
analyzed using different principles of these two properties in line with the chemical structure of the
compounds. Furthermore, the effect of intermolecular force of attraction and geometric isomerism were
analyzed using the data gathered for melting points. Stronger intermolecular force indicates higher melting
and boiling points. The compound of the strongest intermolecular force is known as the hydrogen bonding
while the weakest bond is classified as the London-Dispersion force. This is because the stronger its
intermolecular forces between molecules the harder for it break its bond thus requires a higher energy
producing higher melting and boiling points. The geometric isomerism is also significant to the difference of
the melting point which is dependent on the its geometric structure and the formation of substituents. It is
classified as an isomer wherein trans-isomers forms a stronger bond and yields to a higher melting point than
a cis-isomer. Compound with more branching atoms exhibits greater boiling point. And also the impurities to
a solution affects its boiling point. These are some of the factors which greatly affect the melting point and
boiling point of an organic compound.
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