COMPARATIVE INVESTIGATION OF ORGANIC COMPOUNDS

Jyle Fraium L. Dino​, Franc Ison P. Dy, Micole Manolo I. Gabriel,

Demi Louise L. Go, Vheverli Whendel P. Go
Group 4 2A Medical Technology Organic Chemistry Laboratory

ABSTRACT
The experiment aimed to differentiate organic compounds, specifically cyclohexane, DCM, ethanol, phenol, benzoic
acid, ethyl acetate, and ethylamine, in terms of their certain intrinsic physical properties, acidity and basicity, and
behavior towards ignition. Intrinsic physical properties of these organic compounds were determined by observing
their physical state, color, and odor at room temperature. The physical state and appearance of the organic
compounds were liquid and clear respectively except benzoic acid, which was solid amorphous. The color of the
compounds were colorless except phenol and benzoic acid, which were red-orange and white, respectively. All
compounds differed in odor except cyclohexane and benzoic acid, which were odorless. The solubility and miscibility of
these organic compounds were determined using water, 5% NaOH solution, and 5% HCl solution. Cyclohexane and
DCM were immiscible in these solvents, while ethanol, ethyl acetate, and ethylamine were miscible. Phenol was
slightly immiscible in water, miscible in 5% NaOH solution, and immiscible in 5% HCl solution. Benzoic acid was
slightly soluble in water, soluble in 5% NaOH solution, and insoluble in 5% HCl solution. The reaction to litmus paper
was used to determine the acidity and basicity of these organic compounds. Most of the compounds were neutral
except for phenol and benzoic acid, which were acidic, and ethylamine, which was basic. Ignition test was also
conducted to determine the flammability of the compounds. DCM, phenol, and benzoic acid were non-flammable while
the rest were flammable. Organic compounds have different properties due to their type of bonds and functional
groups.

INTRODUCTION divided into two groups, namely aliphatic and

Organic compounds are compounds that
contain carbon atoms in their molecules, usually
forming bonds with elements such as hydrogen,
nitrogen and oxygen. The carbon chains of
organic compounds vary in terms of length and
shape as the carbon atoms may form double and
triple bonds with elements. Having a valency of
4, carbons can form more types of bonds with
other atoms and more complex compounds [2].
The likely variation of the molecular composition
of organic compounds is due to this [3]. Organic
compounds are also classified into hydrocarbons
and hydrocarbon derivatives with the
replacement of hydrogen by a functional group or
a different element as the basis. Carbons bond
not only with themselves but also with hydrogen
to form chains and rings, the hydrocarbons. The
carbon skeletons are hydrophobic as the bond
formed between carbon and hydrogen is
covalent, thus nonpolar. More hydrophilic carbon
skeletons are made by attaching functional
groups, and the differences between the carbon
skeletons and functional groups cause different
and specific chemical properties of the organic
molecules [4].
Composed entirely of carbons and hydrogens,
hydrocarbons are considered as the simplest
class of organic compounds. They are further
aromatic hydrocarbons. Aliphatic hydrocarbons
lack benzene rings and are classified as alkanes,
alkenes and alkynes based on the structure and
bonding of the carbon chain. They are also
flammable [5]. On the other hand, aromatic
hydrocarbons contain benzene rings, possess
pleasant odors and have special stability due to
delocalized pi electron density shared between all
the carbon atoms [6].
As organic compounds have different intrinsic
physical properties, their physical states may
vary at room temperature, odor, color and
solubility in different solvents. The solubility of
the organic compounds in acids and bases also
determine their acidity and basicity, and ignition
of the organic compound determine their
flammability.
The objectives of the experiment are to
differentiate organic compounds in terms of
certain intrinsic physical properties, behavior
towards ignition and infrared spectra of their
functional groups.
EXPERIMENTAL
A. Compounds Tested
Cyclohexane, Dichloromethane (DCM), Ethanol,
Phenol, Benzoic Acid, Ethyl Acetate, Ethylamine
 The condensed structural formula of the test
compounds used are the following:
Figure 1.​ Cyclohexane
CH​2​Cl​2
Figure 2​. Structure of DCM
CH​3​CH​2​OH
​ Figure 3.​ Structure of ethanol
Figure 4​. Phenol
​ Figure 5.​ Benzoic acid
​Figure 6.​ Ethyl acetate
CH​3​CH​2​NH​2
Figure 7.​ Structure of ethylamine
B. Procedure
1. Physical State, Appearance, Color and
Odor
The physical state, appearance and color of
each of the compounds at room temperature
were observed and determined. The odor was
also described through a wafting motion.
2. Solubility Properties in H​2​O, 5% NaOH
solution and 5% HCl solution
The sample compounds were introduced into a
clean and dry test tube. For the liquid
compounds, 4 drops of each of the samples were
placed into the test tube while 0.1 g was utilised
for the solid sample. The solid samples were also
pulverized in order to increase the surface area.
Three millilitres or 96 drops of each solvent was
added dropwise to the test tubes. After the
addition of the solvents to the compounds, the
changes in color, warming, or effervescence were
noted. Furthermore, the solubility of the sample
in each of the solvents were described as miscible
or immiscible.
​ Figure 1.​ Solid benzoic acid being grinded
Figure 2. Addition of 3 mL or 96 drops of the
solvent dropwise
Figure 3. Phenol being immiscible with the H​2​O
and HCl Figure 6. Cyclohexane mixed with different
solvents

Figure 7. Ethanol miscible with ​H​2​O, NaOH and

Figure 4. Benzoic acid immersed in various HCl
solvents

Figure 8.​ DCM mixed with H​2​O, NaOH and HCl

Figure 5. Ethylamine miscible with H​2​O, NaOH
and HCl
 Figure 11.​ An evaporating dish and match were
Figure 9.​ Ethyl acetate with various solvents the materials used during the ignition test

3. Reaction with Litmus Paper RESULTS AND DISCUSSION

Few drops of the miscible samples were tested
with a red and blue litmus paper in order to
determine if the compounds were acidic or basic.
A. Observation of Physical State at Room
Temperature, Color, and Odor of Organic
Compound Sample
​Most of the hydrocarbons were colorless,
except phenol and benzoic acid, which were
red-orange and white in color, respectively. When
liquid compounds were stored for a long period of
time, they oxidized. More often than not, these
oxidized products had intense colored and formed
of crystals. Phenol became red-orange in color
upon oxidation, while benzoic acid had white
crystals. The odors of the samples were quite
similar to each other but still had different
identity which made them unique from each
other. Cyclohexane and benzoic acid both were
odorless. DCM had acetone-like odor. Ethanol
had alcohol-like odor. Phenol had pastel-like
odor. Ethyl acetate had plastic balloon odor.
Ethylamine had ammonia-like odor because its
functional group is amine.

Table 1. ​Intrinsic property of organic compounds

Figure 10. Various compounds undergoing the
litmus paper test Physical Appear Color Odor
state at - ance
RT
4. Ignition Test
Three to five drops of the liquid compounds Cyclo - liquid clear colorless odorless
and a pinch of the solid compounds were placed hexane
in a small evaporating dish and lit with a match.
The flammability of each of the compounds, DCM liquid clear colorless acetone
formation of soot and color of flame produced
were observed. Ethanol liquid clear colorless alcohol

Phenol liquid clear red - pastel-like

orange
Benzoic solid amorp - white odorless acetate
acid hous
Ethyl - miscible miscible miscible
Ethyl liquid clear colorless plastic amine
acetate balloon

Ethyl - liquid clear colorless ammonia C. Reaction with Litmus Paper

amine The acidity, basicity and neutrality of the
organic compounds were determined by their
reaction with litmus paper. Acidic solution turned
B. Test for Solubility Properties of Samples
blue litmus paper to red and red litmus paper to
in ​H​2​O​, 5% NaOH, and 5% HCl solution
red. Basic solution turned the red litmus paper
​The solubility was done to be familiar with the
to blue and blue litmus paper to blue. Neutral
chemical nature of the compounds. Water 5%
solution retained its color.
NaOH, and 5% HCl were the three solvents used
Based on the experiment, phenol and benzoic
in describing the solubility properties and
acid were acidic while ethylamine was basic.
miscibility of the compounds. Solubility properties
Ethanol and ethyl acetate were observed to be
had something to with their polarity of the two
neutral solutions.
substances and the intermolecular forces
attraction during the solution process. Polar
Table 3. Acidity, basicity, and neutrality of
compounds would dissolve or be miscible in
sample
water because water is a strong polar substance
and polarity follows the “like dissolves like” Reaction with litmus
principle. Ethanol and ethylamine were found to paper
be polar compounds. The solubility in 5% NaOH
Cyclohexane Not applicable
solution of a water insoluble sample was an
indication of the presence of acidic functional DCM Not applicable
group. Cyclohexane and DCM were immiscible in
5% NaOH solution while benzoic acid was slightly Ethanol Blue → Blue
soluble. The rest were miscible. The solubility in Red → Red
5% HCl solution was an indication of the
Phenol Blue → Red
presence of basic functional group. Ethanol, ethyl
Red → Red
acetate, and ethylamine were miscible in 5% HCl
solution while the rest were immiscible aside Benzoic acid BLue → Red
from benzoic acid which was insoluble. Red → Red

Table 2. Solubility of organic compound sample Ethyl acetate Red → Red

in different solvents Blue → Blue

H 2O 5% NaOH 5% HCl Ethylamine Red → Blue

solution solution Blue → Blue

Cyclo - immiscible immiscible immiscible

hexane D. Ignition test
Ignition test was used to indicate the presence
DCM immiscible immiscible immiscible of unsaturated or high carbon to hydrogen ratio.
The degree of luminosity could be assessed by
Ethanol miscible miscible miscible the presence of yellow flame and soot. Flame
with soot was due to the incomplete combustion
Phenol Slightly miscible immiscible
immiscible of aromatic compounds. Incomplete combustion
caused the formation of an unburned carbon. The
Benzoic Slightly soluble insoluble greater the number of carbon atoms, the higher
acid soluble the degree of luminosity. Moreover, the higher
carbon: hydrogen ratio, the higher the degree of
Ethyl - immiscible miscible miscible luminosity. Aromatic compound had the greatest
degree of luminosity among unsaturated Chemistry)/Alkanes/Reactivity_of_Alkanes/Compl
hydrocarbon and saturated hydrocarbon. It was ete_vs._Incomplete_Combustion_of_Alkanes
followed by the unsaturated hydrocarbon and 11/13/18
saturated hydrocarbon, respectively. [2] Markgraf, B. (2018). What is an Organic
2C 10 H 22 + 31O2 → 20CO2 + 22H 2 O Compound?
https://sciencing.com/what-is-an-organic-compo
Yellow or luminous flame were the indication of und-13712143.html 11/13/18
incomplete combustion because carbon was not [3] General Introduction to Organic Compounds:
completely oxidized. Properties, Uses with Videos (2018). General
2C 2 H 2 + 5O2 → 4CO2 + 2H 2 O + heat Introduction of Organic Compounds.
https://www.toppr.com/guides/chemistry/organic
Table 4. Flammability and luminosity of the -chemistry/general-introduction-organic-compou
sample nds/ 11/13/18
[4] Mott, V. (n.d.). Introduction to Chemistry.
Ignition Test
https://courses.lumenlearning.com/introchem/ch
Cyclohexane Flammable apter/functional-groups/ 11/13/18
(yellow-orange with [5] (n.d.). What is Hydrocarbon? - Definition,
soot) Formula and Compounds.
https://study.com/academy/lesson/what-is-hydro
DCM Non-flammable carbon-definition-formula-compounds.html
11/13/18
Ethanol Flammable (blue
[6] Boundless. (n.d.). Boundless Chemistry.
without soot)
https://courses.lumenlearning.com/boundless-ch
Phenol Non-flammable emistry/chapter/aromatic-hydrocarbons/
11/13/18
Benzoic Acid Non-flammable

Ethyl acetate Flammable (yellow

with soot)

Ethylamine Flammable (blue with

soot)

In conclusion, organic compounds have

different properties that make them distinct from
the other compounds. The types of bond and
functional groups of these organic compounds
affect their properties. Based on the solubility
observed, ethanol and ethylamine are polar
compounds. Phenol and benzoic acid are acidic
while ethanol, ethylamine is basic. Among the
seven organic compounds,cyclohexane, ethyl
acetate, and ethylamine are the three flammable
with soot. Flame with soot is due to the
incomplete combustion of compounds.
Incomplete combustion is caused by the
formation of an unburned carbon.

REFERENCES
[1] ​Libretexts (2017). Complete vs. Incomplete
Combustion of Alkanes.
https://chem.libretexts.org/Textbook_Maps/Orga
nic_Chemistry/Supplemental_Modules_(Organic_