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Professor Oliver Villaflores, School of Chemical Engineering, Chemistry, Biological Engineering and Materials
Science Engineering, Mapa Institute of Technology; 2Castro, Ethan Zachary G., Pasia, Abraham Paul L., Pulido,
Froileth S., CHM145L-C11, School of Chemical Engineering, Chemistry, Biological Engineering and Materials
Science Engineering, Mapa Institute of Technology
ABSTRACT
The Structural Theory of Organic Chemistry implies that the chemical structures of compounds, most
especially organic compounds, greatly influence their physical and chemical properties. Two of the essential physical
properties of organic compounds are their boiling point and melting point, or the temperature where the organic
substance shall begin to boil and melt, respectively. The experiment primarily aims to validate the effect of the chemical
structure of various organic compounds to their two aforementioned physical properties by comparing the boiling point
and melting points of various organic compounds with various chemical structures. Chemical structure primarily refers
to the intermolecular forces of attraction occurring within the molecules of an organic compound, and geometric
isomerism, or the variety of molecular geometries or arrangements that molecules of a certain organic compound may
be arranged. To address the primary objective of the experiment, a variety of solid organic compounds, including
naphthalene, benzoic acid, salicylic acid, benzoin, and urea were heated to determine their melting point range
experimentally, using the Thomas-Hoover Apparatus. Further, to test the effect of geometric isomerism, finely ground
maleic (cis) and fumaric (trans) acids, which are isomers of each other, were tested in the same manner. Moreover, to
test the effect of purity of substances on the melting point, pure and impure samples of urea were tested in the same
way. In addition, various types of liquid organic substances were tested in terms of their boiling points by applying heat
using a hot plate. Among these include n-Butanol, 2-Butanone, n-Hexane, n-Heptane, and propanoic acid. Finally, the
effect of more branched molecular structures on the boiling point was tested by treating n-butyl alcohol, sec-butyl
alcohol, and tert-butyl alcohol in the same manner. Doing these, the researchers were able to validate the effects of
various chemical structures on the melting and boiling points of organic substances. It was proven that as the
intermolecular forces occurring within an organic compound are stronger, its boiling point and melting point is higher
than those with weak intermolecular forces. On the other hand, the trans isomers, such as fumaric acid, have higher
melting points than those of the cis isomers, like the maleic acid. Finally, as branching within an organic compound
increases, its boiling point decreases due to the increase in the surface area of the compound.
Keywords: structural theory, organic compounds, intermolecular forces, geometric isomerism, branching
INTRODUCTION
The melting point of a solid substance is
the point at which the solid state changes into
liquid state at an atmospheric pressure; at this
point, the solid and liquid phases exist in an
equilibrium. On the other hand, the boiling point of
a substance is the temperature in which the vapor
pressure of the liquid is the same with the
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METHODOLOGY
The experiment is divided into two parts
which are melting point and boiling point. It is
subdivided into a single part: structural effect,
which is still subdivided into few parts, for melting
point, intermolecular forces of attraction,
geometric isomers and effect of purity on melting
point range; for boiling point: intermolecular forces
of attraction and branching.
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TABLE 1
Compound
Benzoic
Acid
Benzoin
Naphthalene
Salicylic
Acid
Urea
Melting
Point
True
Value
112 123
118
122.41
130 138
74 86
134
80
132
80.26
151 157
154
159
127 135
131
133
T1
T2
T1
T2
Melting
Point
True
Value
300
304
302
287
127
132
130
135
T1
120
127
T2
129
135
Melting point
125
131
T1
T2
Boiling
Point
117
80
100
True
Value
117.4
79.64
98.42
141
141.2
70
68
References
Brittain, C. G. (2009, May 18). Using Melting Point to
Determine Purity of Crystalline Solids.
Retrieved from The University of Rhode
Island:
http://www.chm.uri.edu/mmcgregor/chm228/
use_of_melting_point_apparatus.pdf
Clark, J. (2012). STEROISOMERISM - GEOMETRIC
ISOMERISM. Retrieved from Chemguide:
http://www.chemguide.co.uk/basicorg/isomer
ism/geometric.html
Feynman, M. (2014). Why do branched chain
compounds have lower boiling points than
the corresponding straight chain isomers?
Retrieved from Chemistry StackExchange:
http://chemistry.stackexchange.com/questio
ns/6944/why-do-branched-chaincompounds-have-lower-boiling-points-thanthe-corresponding
Master Organic Chemistry. (2015). 3 Trends That
Affect Boiling Points. Retrieved from Master
Organic Chemistry:
http://www.masterorganicchemistry.com/201
0/10/25/3-trends-that-affect-boiling-points/
Shimizu, K. (2015). HOW TO: PREDICT BOILING
POINT AND MELTING POINT TRENDS.
Retrieved from Organic Chemistry FAQ:
http://www.chem.sc.edu/faculty/shimizu/333/
Chem_333/2b.i.html
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