CHM142L/B11 Organic Chemistry 1 Laboratory

1st Quarter AY 2012-2013

Mapua Institute of Technology

School of Chemical Engineering and Chemistry
Muralla St., Intramuros, Manila
Melting Point and Boiling Point of Organic Compounds
Group No. 5
Manacup, Cris Vincent L.
Oblena, Adrian D.
Ong, Joshua Jyro B.*
*Leader
ABSTRACT
In compounds, two of the physical properties affected by the varying structures
are melting point and boiling point. Through the use of the Thomas-Hoover Melting
Point Apparatus or the micro method, the melting and boiling point of organic
compounds are now determined.
The aim of this experiment is to know the factors affecting the trend of melting
point and boiling point. These factors are all based on the structural theory of
compounds. Including are the intermolecular forces of attraction between molecules,
geometric isomerism, purity for melting point determination; and intermolecular
forces of attraction between molecules and branching for the boiling point
determination.
From the structure, intermolecular forces can be observed (hydrogen bonding,
dipole-dipole interaction, or London dispersion forces)*. Along with these forces,
geometric isomerism affects also. In terms of purity, a pure compound has higher
melting point than compound with impurities. Branching, also a factor, makes a
compound smaller in terms of surface area that lowers boiling point.
*arranged from strongest to weakest
INTRODUCTION
Melting point of a compound is the temperature at which liquid and solid coexist
in equilibrium where a substance in solid form for changes to a liquid. Boiling point,
on the other hand, is the temperature at which the vapor pressure of a liquid is equal
to the external pressure where a liquid form of the substance changes to a gas.
These properties vary from structure to structure and can be explained by the
structural theory. This involves the intermolecular forces of attractions for each
molecule, the order in which atoms are put together in molecules and the electrons
that hold them together. This is the reason behind the melting and boiling point of
each compound.
At this point in time, there are inventions of apparatus for the melting point and
boiling point determination that are easy to use, fast and digital. These sets are
available to the market for a more accurate reading in these physical properties.
Experiment 1 | Melting Point and Boiling Point of Organic Compounds
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CHM142L/B11 Organic Chemistry 1 Laboratory

1st Quarter AY 2012-2013

METHODOLOGY
Melting Point Determination
Capillary tubes were sealed first on one end by heating it
in a Bunsen burner.
Using reagent-contained capillary tubes about 5-6 mm in
height, it was subjected into the Thomas-Hoover melting
point apparatus (Fig 1). Melting point range determined by
two measurements: the temperature at which the reagent
starts to liquefy and the temperature at which the reagent
was completely liquefied.
Fig 1. Thomas-Hoover Melting Point Apparatus
REAGENTS: Benzoic acid, Benzoin, Fumaric acid, Maleic acid,
Naphthalene, Pure and Impure Urea, Salicylic acid, Silicone fluid
Boiling Point Determination
For the boiling point, micro method was used for
determining it. Micro method is shown in Fig 2. The capillary
tube is placed in a micro test tube containing 2-3 drops of
the reagent. Firmly attached is the thermometer beside the
test tube with a rubber band. Boiling point is determined by
two measurements: the temperature at which bubbles come
out of the capillary tube and the temperature at which the
liquid comes out of the capillary tube.
Fig 2. Micro Method
REAGENTS: 2-Butanone, Glycerol, n-Butanol, n-Hexane, n-Pentane, Propanoic Acid,
sec-Butanol, tert-Butanol

RESULTS AND ANALYSIS

I.
Melting Point
A. Structural Effect
a. Intermolecular
Forces
of
Attraction
COMPOUND
MELTING POINT
Benzoic Acid
123 deg C
Benzoin
131 deg C
Naphthalene
81.5 deg C

Salicylic Acid
Urea

156.5 deg C
131 deg C

Based on the data obtained from the

experiment, salicylic acid has the highest
melting point; then, benzoin and urea;
next is benzoic acid; and lastly,
naphthalene.

Salicyclic
acid
can
form
two
intermolecular hydrogen bonds. Benzoin
Experiment 1 | Melting Point and Boiling Point of Organic Compounds
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CHM142L/B11 Organic Chemistry 1 Laboratory

1st Quarter AY 2012-2013

can form an intermolecular hydrogen

bond and experiences London dispersion
forces. Urea can form four hydrogen
bonds
but
nitrogen
is
less
electronegative than oxygen in the
salicylic acid and benzoin. Benzoic acid
can also have a hydrogen bond but is
weaker than the hydrogen bonds of urea.
Naphthalene has the lowest melting
point due to the formation of London
dispersion forces.

b. Geometric Isomers
COMPOUND
MELTING POINT
Maleic Acid
138 deg C
Fumaric Acid
200 deg C
Maleic acid and fumaric acid are two
geometrical isomer of butenedioic acid.
Here are their structures:

Maleic Acid

Fumaric Acid

The reason why fumaric acid has

higher melting point is because of the
hydrogen bonding. Maleic acid can only
form one intermolecular hydrogen bond
compared to the two available to fumaric
acid.
B. Effect of Purity
COMPOUND
MELTING POINT
Pure Urea
131 deg C
Impure Urea
127 deg C
Pure urea melts slower than the
impure one. It is because impurities
disturb to the structure of the pure urea
then lowering its melting point.

II.

Boiling Point by a Micro Method

A. Structural Effect
a. Intermolecular
Forces
of
Attraction
COMPOUND
BOILING POINT
n-Butanol
117.75 deg C
2-Butanone
80 deg C
n-Pentane
36.1 deg C
Propanoic Acid
141 deg C
n-Hexane
69 deg C

Based on the data obtained from the

experiment, propanoic acid has the
highest boiling point; then, n-butanol
and 2-butanone; next is n-hexane; and
lastly, n-pentane.
Propanoic acid can form a hydrogen
bond and it experiences dipole-dipole
interaction. n-Butanol can also form a
hydrogen
bond.
2-butanone
then
experiences dipole-dipole interaction. nHexane
and
n-pentane,
non-polar
compounds,
experiences
London
dispersion forces, n-hexane has higher
boiling point than n-pentane because it
has more carbon atoms even both
experience London dispersion forces.
b. Branching
COMPOUND
BOILING POINT
n-Butanol
117.75 deg C
sec-Butanol
99 deg C
tert-Butanol
82.5 deg C

1-butanol

2-butanol

Experiment 1 | Melting Point and Boiling Point of Organic Compounds

3-butanol
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CHM142L/B11 Organic Chemistry 1 Laboratory

1st Quarter AY 2012-2013

Due to branching, smaller surface

area results. With smaller surface area,
London dispersion forces are weak so, as
a result, there will be lowering of boiling
point. N-butanol has no branch, while
sec-butanol and tert-butanol has more
branches than the n-butanol.
CONCLUSION

Intermolecular forces of attraction

for covalent bonding can be hydrogen
bond as the strongest, dipole-dipole
present in polar covalent molecules, or
London dispersion force as the weakest
present in non-polar covalent molecules.
Every molecule experiences any of the
three bonds.
Isomers are chemically identical
molecules with different structure. This is
interconnected with the intermolecular
forces of attraction.

In this experiment, objectives were

achieved. The factors that can affect
melting point and boiling point are
intermolecular
forces
of attraction,
isomerism, purity, and branching.
Purity is the degree of absence of contaminants in a compound. The more pure a
compound is, the higher its melting and boiling point.

Experiment 1 | Melting Point and Boiling Point of Organic Compounds

Branching, in the structure, makes the surface area smaller resulting to weaker
London dispersion forces then lowers the melting and boiling point.
With these factors, there is a varying melting and boiling points of organic
compounds since there are variety of structures of these compounds.
REFERENCES
http://www.chemicalforums.com/index.php?topic=25328.0. (n.d.).
Klein, D. Organic Chemstry. C&E Publishing, Inc.
Whitten, K. W., Davis, R. E., Peck, M. L., & Stanley, G. G. Chemistry. C&E Publishing,
Inc.

Answers to Guide Questions

1. Rank the following compounds in decreasing melting point: benzoic acid, benzoin,
naphthalene, salicylic acid and urea. Justify your rank by citing the intermolecular
forces of attraction present in the particular compound.
Salicylic acid > Benzoin > Urea > Benzoic acid > Naphthalene
It is ranked as it is due to the effect of intermolecular forces of attraction. Salicylic
acid got the highest melting point among the rest because it can form two hydrogen
bonds, the strongest bond in covalent bonding, and has a high molecular weight.
Next, benzoin can form one intermolecular hydrogen bond and experiences London
dispersion forces. Urea can form four hydrogen bonds but nitrogen is less
electronegative than oxygen in the salicylic acid and benzoin. Benzoic acid can also
have a hydrogen bond but is weaker than the hydrogen bonds of urea. Naphthalene
has the lowest melting point due to the formation of London dispersion forces, the
weakest bonds in covalent bonding.

2. How does molecular geometry affect melting point of an organic compound?

Molecular geometry can affect the melting point of an organic compound because
with molecular geometry means the structure and how the atoms were connected to
each other so different geometries made the intermolecular forces of attraction
between its molecules are changed resulting to change in melting point.
3. How do impurities affect the melting point of an organic compound?
Impurities in the organic compounds lowers it melting point because it disturbs the
structure of the compound being impure by others.
4. In general, what are the factors that affect the melting point of an organic
compound? What are the effects?
The factors affecting the melting point of organic compounds are intermolecular
forces of attraction, their molecular geometry between isomers, and its purity.
Intermolecular Forces of Attraction
Strongest is the hydrogen bonding; next is dipole-dipole interaction; the
weakest is the London dispersion forces.
From the structure of a compound, you can determine if what kind of
interaction of molecules is present in there. When a compound can form a
hydrogen bond, it can have high melting point. The decrease in melting point
goes on with the dipole-dipole present in polar covalent bonding and decreases
more with the London dispersion force present in non-polar covalent bonding.
Molecular Geometry between Isomers
This is dealing also with the intermolecular forces of attraction. Isomers are
chemically identical molecules with different structure. Different structure made
the intermolecular forces of attraction change so as the melting point.
Purity
The lesser impurities a compound has, the lower its melting and boiling point
due to the disturbance made by the impurities in the structure
5. Consider the boiling point of n-Butanol, 2-Butanone, n-Pentane, and Propanoic
acid. How does polarity affect the boiling point of organic compounds?
Polarity affects the boiling point of an organic compound because polarity shows
that there is an induction occurring or dipole moment exhibit. As a whole, there is a
dipole-dipole interaction that elevates boiling point.
6. Compare the boiling points of n-Pentane and n-Hexane. Which has the higher
boiling point? Justify your answer.
N-Hexane has the higher boiling point than n-pentane since it has higher molecular
weight, larger surface area, stronger London dispersion forces, and it has something
to do with the number of carbon atoms.
7. Compare the boiling points of n-butyl alcohol, sec-butyl alcohol, and tert-butyl

alcohol. What makes the difference?

In terms of boiling point, n-butyl alcohol > sec-butyl alcohol > tert-butyl alcohol.
This is because of branching. Due to branching, smaller surface area results. With
smaller surface area, London dispersion forces are weak so, as a result, there will be
lowering of boiling point. N-butanol has no branch, while sec-butanol and tert-butanol
has more branches than the n-butanol.
8. In general, what are the factors that affect the boiling point of organic compounds?
What are the effects of each factor?
As

a whole, boiling point is affected by the following factors:

Intermolecular forces of attraction
Polarity
Branching

Intermolecular Hydrogen Bonding

The more of this force of attraction, the higher the boiling point.
Polarity
This involves dipole-dipole interactions since dipole moment is an indicator of
polarity; if an organic compound is polar and that it experiences dipole moment,
the higher the boiling point but is lower than a compound with an intermolecular
hydrogen bonding.
Branching
This involves London dispersion forces. If there are less brancj=hing of
molecules, the larger the surface area, the stronger the London dispersion forces,
the higher the boiling point.