COMPARATIVE INVESTIGATION OF ORGANIC COMPOUNDS

Harvie M. Barcellano, Dariene Joie B. Bautista, Florianne May D. Beltran, Jerika Prem M. Benjamin,
Rochelle Anne C. Burata and Emmanuel R. Caliwag
Group 2
2G Medical Technology
Organic Chemistry Laboratory
ABSTRACT

The objective of the experiment is to differentiate organic compounds in terms of certain intrinsic physical properties,
behavior towards ignition test, and infrared spectra of their functional groups. Physical properties are determined by
observing the samples physical state at room temperature, color and odor. Solubility and miscibility were tested using
the following reagents: water, 5% NaOH solution, and 5% HCl solution. Only dichloromethane appeared to be
immiscible in the three solvents, the rest being slightly miscible or miscible. Acidity and basicity of the compounds
were determined by the use of litmus paper. Only phenol and benzoic acid was observed to be acidic, while ethylamine
as the sole basic compound, the rest being neutral. Ignition test was also conducted, taking note of the flame
produced if flammable. Among the samples, only dichloromethane, phenol, and benzoic acid were identified to
be non-flammable. Infrared spectroscopy, which is useful for determining the functional groups present in an
organic compound, was used to find the IR peaks of each sample. From the experiment, it could be concluded

that organic compounds have different properties and that the types of bond and functional groups of
these organic compounds affect those properties.
INTRODUCTION
Generally, 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. Specifically, organic compounds are
conveniently classified as different classes of
hydrocarbon derivatives based on the substituent
element or group of highest priority to the
hydrocarbon. Functional groups present in an
organic compound can be determined using
infrared spectroscopy[1].
Organic compounds are the complex
compounds
of
carbon.
Because
carbon
atoms bond to one another easily, the basis of
most organic compounds is comprised of carbon
chains that vary in length and shape. Hydrogen,
nitrogen, and oxygen atoms are the most
common atoms that are generally attached to the
carbon atoms. Each carbon atom has 4 as its
valence number which increases the complexity
of the compounds that are formed. Since carbon
atoms are able to create double and triple bonds
with other atoms, it further also raises the
likelihood for variation in the molecular make-up
of organic compounds.
Hydrocarbons are the simplest class of organic
compounds and are composed solely of hydrogen
and carbon. This class can be further divided into
two groups: aliphatic hydrocarbons and aromatic
hydrocarbons. Aliphatic hydrocarbons can be
classified based on the structure and bonding of
the carbon skeleton into three groups: alkanes,
alkenes, and alkynes. Aromatic hydrocarbons or
arenes, which contain a benzene ring, were
originally named for their pleasant odors. These
compounds possess special properties due to the

delocalized electron density in benzene, including

additional stabilization due to the system of
conjugated rings consisting of unsaturated bonds,
lone pairs, and empty orbitals[3].
Organic compounds possess different physical
properties, which are intrinsic[1]. They may vary
in their physical state at room temperature,
which can indicate the strength of interactive
forces that exist between its molecules, color,
odor and solubility indifferent reagents. The
experiment
aims
to
differentiate
organic
compounds in terms of: certain intrinsic physical
properties,
behavior
towards
ignition,
and
infrared spectra of their
functional groups.
Cond
ensed structural formula
of the
compounds used[2]:
1. Cyclohexane

2.DCM
CH2Cl2

3. Ethanol
CH3CH2OH

Drops of the sample tested its aqueous solution

with red and blue litmus papers. Color changes
with both litmus papers were noted.

4. Phenol

5. Benzoic Acid

4. Ignition Test
3-5 drops of the liquid and pinch amount of
solid sample were placed in a small evaporating
dish and lighted with a match stick. Any flame
produced and observed was noted. The color of
the flame and burning time were also noted.
5. Infrared (IR) Analysis
The type of principal bonds of each sample
compound was identified. The book, Reference 1,
was used as a guide in determining the wave
number range of each organic compound, as well
as its intensity.

RESULTS AND DISCUSSION

6. Ethyl Acetate

7. Ethylamine
CH3CH2NH2

EXPERIMENTAL
A. Compounds Tested
Cyclohexane, Dichloromethane, Ethanol, Phenol,
Benzoic acid, Ethyl acetate, and Ethylamine
B. Procedure
1. Physical State, Color and Odor
The physical state of the sample was observed
in room temperature. Color and odor was noted.
2.Solubility Properties
The samples were introduced into clean and
dry test tubes. Four drops of each sample were
introduced if the sample is a liquid; and 0.1 g of
the sample was introduced if the sample is solid.
The solid samples were grinded to increase the
surface area. The solvent was added drop wise,
counting the number of drops of solvent added to
a total of 3 mL. Any color changes, warming or
effervescence,
soluble/insoluble,
miscible/immiscible were noted.
3. Reaction with Litmus Paper

All of the hydrocarbons tested were colorless,

except phenol, which is orange in color, and
benzoic acid which is white in color. The odors of
the compounds were quite similar but it has its
unique differences that can be seen on Table 1.
Solubility test is done to be familiar with the
chemical nature of the compounds. Water, 5%
NaOH and 5% HCl were used to describe the
compounds' solubility properties and miscibility.
Based on the results, cyclohexane was observed
to be miscible in water, and slightly miscible in
5% NaOH and 5% HCl; DCM appeared to be
immiscible in the 3 solvents; ethanol, phenol and
ethylamine were miscible in the 3 solvents;
benzoic acid, miscible in water, slightly miscible in
5% NaOH and 5% HCl; Ethyl acetate was
immiscible in water and 5% NaOH, and was
miscible in 5% HCl.
Reactions with litmus paper indicate the
acidity/basicity of water-soluble samples. If a
blue litmus paper turns into red, then the sample
is acidic, but when a red litmus paper turns into
blue, then the sample is basic. The litmus paper
that retains its color indicates a neutral
compound.
Based
on
the
experiment,
cyclohexane, dichloromethane, ethanol, and ethyl
acetate appeared to be neutral. On the other
hand, phenol and benzoic acid was observed to
be acidic and ethylamine as the sole basic
compound.
Solubility of organic compound also indicates
acidity and basicity of the sample. The result of
ignition
test
indicates
the
presence
of
unsaturation or high carbon to hydrogen ratio.
Among the samples, only dichloromethane,
phenol, and benzoic acid were identified to be
non-flammable.
The degree of luminosity can be assessed by
the presence of yellow flame and soot. The
aromatic compounds burn with sooty flame due

to complete combustion which causes the

formation of an unburned carbon. In terms of
degree
of luminosity:
aromatic
compound>unsaturated hydrocarbon> saturated
hydrocarbon.
Complete combustion is indicated by a blue
flame (non luminous) and there is more heat
than light, the carbon is completely oxidized.
2 C10H22 + 31 O2

20 CO2 + 2 H2O

Incomplete combustion is indicated by a yellow

flame (luminous) and there is much light than
heat, the carbon is not completely oxidized.
[1]
Infrared spectroscopy is particularly useful for
determining the types of bonds that are present
in a molecule. The primary use of IR is to identify
the functional groups present in a molecule.
From the experiment, it could be concluded that
organic compounds have different properties and
that the types of bond and functional groups of
these organic compounds affect those properties.

REFERENCES:
[1] Bathan, G.I., Bayquen, A.V., Crisostomo,
A.B.C., Cruz, C. T., De Guia, R.M., Farrow, F.L.,
Pea, G.T., Sarile, A.S., Torres, P.C. (2014).
Laboratory Manual in Organic Chemistry. Manila:
C&E Publishing, Inc. P.69
[2]
Formulas
of
Inorganic
and
Organic
Compounds. (n.d.). In ChemWiki. Retrieved
November
20
2015
from
http://chemwiki.ucdavis.edu/Physical_Chemistry/
Quantum_Mechanics/09._The_Hydrogen_Atom/A
tomic_Theory/Chemical_Compounds/Formulas_of
_Inorganic_and_Organic_Compounds
[3] What are Organic Compounds?. (n.d.). In
wiseGeek. Retrieved November 20, 2015 from
http://www.wisegeek.com/what-are-organiccompounds.htm

Table 1. Comparative Investigation of Organic Compounds

Test Compounds

Cyclohexane

DCM

Ethanol

Phenol

Benzoic acid

Eth

Physical State at
RT

Liquid

Liquid

Liquid

Liquid

Solid

Liq

Appearance

Clear

Clear

Clear

Clear

Crystalline

Cle

Color

Colorless

Colorless

Colorless

Orange

White

Col

Odor

Diesel-like odor

Kerosene-like
odor

alcohol-like odor

Burnt plastic-like
odor

Odorless

Pla
odo

Solubility in
H 2O

Miscible

Immiscible

Miscible

Slightly miscible

Slightly soluble

Slightly miscible

Immiscible

Miscible

Miscible: orange to
violet

Soluble

Slig
mis
bub
Mis

Slightly miscible

Immiscible

Miscible

Miscible: orange to
white

Slightly soluble

Mis

Reaction with
litmus paper

Blue to Blue
Red to Red

Blue to Blue
Red to Red

Blue to Blue
Red to Red

Blue to Red
Red to Red

Blue to Red
Red to Red

Blu
Red

Ignition test

Flammable:
yellow-orange

Non-flammable

Flammable: blue
and orange

Non-flammable

Non-flammable

Fla
ora

Observed
principal IR
peaks (cm-1)*

C-C stretch:
1200-800, very
W
C-H bend:
1435-1350, S-M
C-H stretch:
3000-2840, S

C-Cl: 580-780, S
C-C stretch:
1200-800, very
W
C-H stretch:
3000-2840, S

O-H stretch:
3700-3100, very S
O-H bend: 14201340, M-W
C-O stretch:
1230-1000, S-M
C-C stretch:
1200-800, very W
C-H stretch:
3000-2840, S
C-H bend: 14751350, S-M

O-H stretch:
3700-3100, very S
O-H bend: 14201340, M-W
C-O stretch:
1230-1000, S-M
C=C ar. stretch:
1620-1480, M-W
C-C stretch: 900600, S-M
C-H stretch:
3100-3000, M-W

C=C ar.
stretch: 16201480, M-W
C-H stretch:
3100-3000, MW
O-H stretch:
3300-2500,
broad S
O-H bend:
1440-1390, M
C=O stretch:
1730-1680, S
C-O stretch:
1320-1210, S

C=
174
C-O
124
C-H
300
C-H
147
M
C-C
120
ver

5% NaOH soln.
5% HCl soln.

[1]

*S = strong, M = medium, W = weak