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Comparative Investigation of Organic Compounds

Hajime Q. Nakaegawa, Maria Elijah A. Natanawan, Jarvin E. Nipales, Jodine P. Novilla, Jonel G. Nuevo
Group 6 2A, Department of Biochemistry, Faculty of Pharmacy, University of Santo Tomas

Abstract
Organic compounds can be classified into hydrocarbons and hydrocarbon derivatives, based on the replacement
of hydrogen by another element or by a group of different elements called a functional group. To be specific, they are
classified as different classes of hydrocarbon derivatives. The primary objective of this experiment was to differentiate
organic compounds in terms of three things: certain physical properties, behavior towards ignition, and infrared spectra of
their functional groups. Four tests were done to investigate seven different organic compounds in the experiment:
observing their physical properties, solubility test, reaction with litmus paper, and ignition test. The comparison of each of
the seven compounds used was discussed in the Results and Discussion. As a result, various properties were determined
in the experiment which plays a vital role in the compound: polarity, acidity/basicity, and the flammability of the compound.

Introduction
An organic compound is any member of
a large class of gaseous, liquid, or solid
chemical compounds whose molecules contain
the element Carbon. Since Carbon atoms bond
easily, its basis will be dependent on its carbon
chain that differs in length, shape and
functional group. All hydrocarbons are
insoluble in water because of their relatively
non-polar. They can be solid, liquid, or gases in
nature. They can be found in petroleum,
natural gas, coal, and also in plants. Most burn
readily and dissolve more readily in alcohol,
than in water. They are being used as fuels and
solvents to manufacture chemicals, plastics,
drugs, and other products.
Organic compounds could be classified
into two major classes: saturated and
unsaturated
hydrocarbons.
Saturated
Hydrocarbons, also called alkanes, are the
simplest class of organic compounds since
they are entirely made up of single bonds and
completely saturated with Hydrogen. Ethers,
alcohols and organic halides are examples of
these. Unsaturated hydrocarbons are those
that are not completely saturated with carbon,
they vary in number of Hydrogen and order of
pi bonds. Each one will differ in reactivity.
The main objective of this experiment
was to differentiate organic compounds in
terms of certain physical properties and
behavior towards ignition.
Organic compounds follow three
interdependent rules of solubility: small organic
molecules are more soluble in water than large

organic molecules; polar organic molecules are


more soluble in water than non-polar
molecules; and compounds in their ionic forms
are more soluble in water than their neutral
forms.
Materials and Methods
Materials
The experiment comprises seven
sample compounds to be used for
investigation, these were namely: cyclohexane,
DCM, ethanol, phenol, benzoic acid, ethyl
acetate, and ethylamine. These were subjected
to four tests which needed secondary materials
like the solvents to be used, namely: 5% HCl
solution, 5% NaOH solution, and distilled
water; litmus paper that were used to
determine the reactivity of the organic
compound; test tubes; test tube holder and
rack; evaporating dish; and matchsticks. The
test tubes should be clean and dry since
contamination might affect the result of the
experiment.
Method
Four major tests were done for the
comparative analysis of compounds. These
were observing the physical state, color, and
odor of the sample; solubility in neutral, acidic,
and alkaline conditions; reactivity with litmus
paper; and the ignition test. Infrared analysis,
which was supposedly included in the
procedure of the manual, was not done in the
experimentation proper.

The seven organic compounds were


now undergone to analysis. The first test i
ncludes taking note of the physical state at
room temperature, color and odor of each
organic sample. The odor was carefully
smelled with a wafting motion to avoid harmful
effects that might occur. Then, solubility test
was now conducted. The researchers used 4
drops of the sample if the sample was liquid
and 0.1g if the sample is solid. The sample
solid should be grinded before subjected into
analysis to increase the surface area of the
sample. The researchers used a calibrated
dropper, which they themselves calibrated it,
and found out that it would take 38 drops to
make 1mL. Add the solvent into the test tubes
containing the organic sample to a total
containing 3mL. Heating is not required in this
test experiment.

Odor

Gasoline-like
odor

Results
Most of the hydrocarbons are colorless.
Before going to the analysis of the compounds,
it is important to take note of the structural
formula of the organic samples. This will
already give us a clue and hint to the results of
the analysis. Table 1.0 contains figures that will
represent the seven organic samples used.
Table 1.0. Condensed Structural Formula of
the Organic Samples Used
Organic Sample
Structural Formula
Cyclohexane
DCM
Ethanol
Phenol

Benzoic Acid

Lastly, the ignition test was done by


placing 3-5 drops of the liquid sample or a
Ethyl Acetate
pinch amount of the grinded solid sample.
Each was lighted with a match. It was
Ethyl amine
observed whether the sample is flammable,
color of flame produced, and the formation of
soot. The burning time of the organic sample
was optional, but the researchers were not
able to compute it.
Table 2.0. Test Results in the Physical State, Color, and Odor
Cyclohexane DCM

Physical
Liquid
state at
room temp.
Appearance Clear
Color

Colorless

Ethanol

Sample
compound

Liquid

Liquid

Solvents used:

Clear

Clear

Colorless

Colorless

Perfumelike-odor

Results and Discussion

If the sample is miscible in water, the


aqueous solution of the organic sample was
reacted with red and blue litmus papers. A
change of blue to red litmus paper simply
means that the sample is acidic, while a
change of red to blue litmus paper means that
the sample is basic. No change in color simply
means that the organic sample is neutral or
has a pH close to 7.

Sample
compound

odorless

Table 3.0. Test Results in the


Reactivity with Litmus Paper

Cyclohexane DCM

Ethanol

H2O

Immiscible

Immiscible

Miscible

S
m

5% NaOH
solution

Immiscible

Immiscible

Miscible

5% HCl
solution

Immiscible

Immiscible

Miscible

Reaction
with litmus
paper

Sample
compound
Ignition
Test

NA

NA

No color
change

water and HCl solution because of its polarity


but not miscible to NaOH since it produces
sodium phenoxide.

Benzoic acid was the lone solid sample


Table 4.0. Test Results in the Ignition
Test
used in the experiment. It is a white crystalline
solid with no odor. It was soluble to NaOH
Cyclohexane DCM
Ethanol
since it is a strong base and insoluble to water
and HCl. It is a non-flammable acidic organic
Flammable
NonFlammabl
sample.

Color of
Flame

Orange

Presence of
Soot

Presence of
soot observed

flammable

NA

Blue

(Non-luminous)

(Luminous)

NA

Presence of
soot
observed

Referring to Tables 2.0, 3.0, and 4.0, it


can be concluded that each of the given
organic sample represents a class of organic
compounds which were presented with
information that can be gathered. A clue that
can be used as a guide is to know the polarity
of the organic sample.
Cyclohexane is a colorless liquid with a
gasoline-like odor which is immiscible to water
but miscible to HCl and NaOH because HCl is
a strong acid, and NaOH is a strong base,
making it a strong nucleophile. With regards to
its flammability, cyclohexane is a non-polar
solvent, meaning weak intermolecular forces,
thats why it gave a non-luminous flame which
generates more heat.

Ethyl acetate was a colorless liquid that


is plastic-balloon like in odor. It is miscible to
water, HCl and NaOH solution. Its flame
produces a luminous yellow flame
Lastly, ethyl amine was a volatile liquid
with a strong smell. It was miscible to all
solvents used and burned with an orange
flame that is non-luminous.
Discussion
A major factor that can be concluded
from the results above would be from the
polarity of the molecule. This will also include
how these intermolecular forces of attraction
present in each sample interact with the
system
and
its
surrounding.
Organic
compounds follow three interdependent rules
of solubility: small organic molecules are more
soluble in water than large organic molecules;
polar organic molecules are more soluble in
water than non-polar molecules; and
compounds in their ionic forms are more
soluble in water than their neutral forms.

Ethanol was a neutral, colorless with a


perfume-like odor. Its flammability test yielded
a blue luminous flame with no smoke. It was
miscible to all solvents used.

Adding up to the concept of flammability


of the organic sample, two types of combustion
were present in the experiment, complete and
incomplete combustion. Complete combustion
is indicated by a non-luminous flame, meaning
there is more heat than light, the carbon
present there is completely oxidized.
Incomplete combustion goes the opposite way,
it is indicated by a luminous flame where there
is much light than heat, carbon here is not
completely oxidized.

Phenol was a clear liquid with a reddishorange color. Phenols are significantly more
acidic than alcohols. It is slightly miscible to

Though the last test of the experiment


was not performed, the IR Spectrometry Test, it
is important to know a little some important

Dichloromethane was a colorless liquid


volatile. It was immiscible to all solvents and is
also non-flammable

concepts that can be retrieved from this kind of


test. The position of the bond depends upon a
number of characteristics of a bond. The higher
the bond order, the higher the wave number for
the stretching vibration for a bond. So in terms
of degree of luminosity, aromatic compounds
will have the greatest length, followed by
unsaturated hydrocarbons, then the saturated
hydrocarbons.
All in all, the experiment succeeded in
showing important intrinsic physical and
chemical properties on some of the classes of
organic compounds. The behavior towards its
ignition and solubility, and even in its IR
spectra, can determine which class of organic
compounds it will belong.
References

Bathan, G., Bayquen, A., Crisostomo, A.B.,


Cruz, C., et.al. (2014). Laboratory
Manual in Organic Chemistry (Revised
Edition). (pp.13-14).
Brown, W., Poon, T. (2011). Introduction to
Organic Chemistry 5th edition. Wiley
International. (pp.64-318).
Clayden, J., Greeves, N., et al (2011) Organic
Chemistry Oxford. (pp.212-250)
Whitten, K., Davis R., Peck, M., & Stanley, G.
(2010). Chemistry (9th Ed.). (p. 463)
Internet
http://www.wiredchemist.com/chemistry/instruct
ional/laboratory-tutorials/c.investigation

Books and Journal Articles


http://www.wfu.edu/chem/courses/organic/com
parativeinvestigation.