COMPARATIVE INVESTIGATION OF ORGANIC COMPOUNDS

Ma. Rio Lauren M. Imbao, Jasmine Mary A. Jamorabon, Kaye Ann B. Labastida,
Kurt Raven T. Lai, Beatrice Andrea G. Lim
Group 5 2C Biochemistry Organic Chemistry Laboratory

ABSTRACT
Organic compounds can be classified into hydrocarbons and hydrocarbon derivatives, based on the replacement of
hydrogen by another element or by group of different elements called functional group. The primary objective of this
experiment is to differentiate organic compounds in terms of certain physical properties, behavior towards ignition,
and determination of acidity and basicity. 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 in the experiment 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 of a large certain intrinsic physical properties, solubility in
class of chemical compounds in which one or different solvents and behavior towards
more atoms of carbon are covalently linked to ignition. [4]
atoms of other elements, most commonly EXPERIMENTAL
hydrogen, oxygen, or nitrogen. [1]
Each carbon atom has 4 valence electron A. Sample Used
which increases the complexity of the compounds The samples used in this experiment
that are formed. Since carbon atoms are able to were: cyclohexane, DCM, ethanol, phenol,
create double and triple bonds with other atoms, benzoic acid, ethyl acetate, and ethylamine.
it further also raises the likelihood for variation in These were subjected to four tests which needed
the molecular make-up of organic compounds. secondary materials like the solvents to be used,
Carbon can also bond with itself and namely: 5% HCl solution, 5% NaOH solution, and
hydrogen to form both chains and rings called distilled water.
hydrocarbons. Because the covalent bond B. Procedure
between carbon and hydrogen is nonpolar, these Four major tests were done for the
carbon skeletons are hydrophobic. Functional comparative analysis of compounds. These were:
groups can be added to carbon skeletons to make observation of physical state, color, and odor of
them more hydrophilic. [2] the sample; solubility in neutral, acidic, and
Organic compounds could be classified alkaline conditions; reactivity with litmus paper;
into two major classes: saturated and and the ignition test. Infrared analysis, which was
unsaturated hydrocarbons. Saturated supposedly included in the procedure of the
Hydrocarbons, also called alkanes, are the manual, was not done in the experimentation
simplest class of organic compounds since they proper.
are entirely made up of single bonds, examples 1. Physical Properties
are Ethers, alcohols and organic halides are The first test includes taking note of the physical
examples of these. Unsaturated hydrocarbons are state at room temperature, color and odor of
those that are not completely saturated with each organic sample. Clean and dry test tubes
carbon, they vary in number of Hydrogen and were used for this to avoid contamination. The
order of pi bonds. Each one will differ in odor was carefully smelled with a wafting motion
reactivity. [3] and not direct smelling to avoid harmful effects
Organic compounds follow three rules of that might occur.
solubility: small organic molecules are more 2. Solubility Test
soluble in water than large organic molecules; The sample was introduced in a clean and dry
polar organic molecules are more soluble in water test tube. 4 drops of each sample was added if
than non-polar molecules; and compounds in the sample is a liquid; and 0.1 g of sample was
their ionic forms are more soluble in water than added if the sample is a solid. The solid samples
their neutral forms. [5] were grinded to increase the surface area before
Organic compounds have different subjected to analysis. The solvent was added
properties. They may vary in their physical state drop wise and counted the number of drops of
at room temperature, color, odor and solubility in solvent added to a total volume of 3mL.
different reagents. The experiment aims to 3. Determination of Acidity and Basicity
differentiate organic compounds in terms of:
If the sample is soluble in water, the aqueous As shown in the table, most of the
solution will be tested with red and blue litmus hydrocarbons are clear except Phenol which is
paper. The color changes in both litmus paper salmon-pink in color and Benzoic acid which is a
was noted. white solid crystalline. The odors of the
4. Ignition Test compounds are quite similar to each other but
Three to five drops of the liquid sample was still have different identity. Cyclohexane have
placed in a small evaporating dish and was gasoline-like odor, Ethanol smells like alcohol,
lighted with a match. If the sample is solid, a Phenol is paste-like while Benzoic acid and DCM
pinch amount was used. The sample was are odorless. Ethyl acetate has plastic balloon
observed if it is flammable or not. The color of odor while ethylamine has ammonia-like odor
flame produced was also noted. because of its functional group, amine.
RESULTS AND DISCUSSION
Before going to the analysis of the Table 3. Solubility Properties of the Samples
compounds, it is important to take note of the
Organic H2O 5% NaOH 5% HCl
structural formula of the organic samples
Sample solution solution
because this will give a hint to the results of the
analysis. Table 1.0 contains the condensed Cyclohexan Immiscible Immiscible Immiscible
structural formula of each sample e
Table 1. Condensed Structural Formula of the DCM Immiscible Immiscible Immiscible
Samples
Organic Sample Condensed Ethanol Miscible Miscible Miscible
Structural Formula
Phenol Miscible Miscible Immiscible
Cyclohexane
Benzoic Insoluble Soluble Insoluble
DCM CH2Cl2 Acid
Ethanol CH2CH2OH Ethyl Immiscible Immiscible Miscible
Phenol Acetate
Ethylamine Miscible Miscible Miscible

Benzoic Acid The solubility properties of organic

compounds using H2O, 5% NaOH solution and
5% HCL solution indicates whether the solid
sample is soluble or insoluble and if the liquid
Ethyl Acetate sample is miscible and immiscible. Solubility of
sample to the solvent is related to polarity of the
Ethyl amine CH3CH2NH2 two substances and the intermolecular forces of
Organic Physical Color Odor attraction during the solution process. The like
Sample State at and
dissolves like principle is involved. Water is a
RT Appeara
nce polar solvent so the sample that is soluble or
Cyclohexane Liquid Clear Gasoline-like miscible with water is also polar. Based on the
Colorless odor results, ethanol, phenol, and ethylamine are
DCM Liquid Clear Odorless polar compounds. The solubility in 5% NaOH
Colorless solution of a water insoluble sample is an
Ethanol Liquid Clear Alcohol-like indication that acidic functional group is present.
Colorless odor Compounds that behave as bases in aqueous
Phenol Liquid Clear Paste-like solution are detected by their solubility in 5% HCl
Salmon- solution. [6]
Pink Ethanol, phenol and ethylamine are
Benzoic Acid Solid White Odorless
miscible while benzoic acid is soluble in 5% NaOH
Crystalline
solution. The rest of samples are immiscible.
Ethyl Liquid Clear Plastic-balloon-
acetate Colorless like odor Ethanol, ethyl acetate and ethylamine are
Ethylamine Liquid Clear Ammonia-like miscible in 5% HCl solution while the rest of the
Colorless odor samples are immiscible and benzoic acid is
insoluble.
Table 2. Intrinsic Properties of the Samples
 higher the number of Carbon atoms, the higher
Table 4. Reactivity with Litmus Paper the degree of luminosity. In addition, the higher
the Carbon: Hydrogen Ratio, the higher the
Organic Sample Reaction with Litmus degree of luminosity. In terms of degree of
Paper luminosity: aromatic compound is the most
Cyclohexane - luminous followed by unsaturated hydrocarbon,
DCM - then saturated hydrocarbon. [7]
Complete combustion is indicated by a
Ethanol Neutral
blue flame (non-luminous) and there is more
(Blue to Blue, Red to Red)
heat than light, the carbon is completely
Phenol Acidic
oxidized.
(Blue to Red, Red to Red)
Benzoic Acid -
2C10H22 +31O2 2CO2 +22H2O
Ethyl acetate -
Ethylamine Basic Incomplete combustion is indicated by a
(Blue to Blue, Red to Blue) yellow flame (luminous) and there is much light
than heat; the carbon is not completely oxidized.
Reaction with litmus paper indicates the
acidity, basicity or neutrality of water-soluble 2C2H2 + 5O2 4CO2 + 2H2O + heat
samples. Acidic solution turns blue litmus paper
to red and red litmus paper to red. Blue litmus Based on the table, cyclohexane, ethyl
paper to blue and red litmus paper to blue acetate and ethylamine are flammable with
indicates a basic solution. Neutral solution is luminous flame while ethanol with non-luminous
characterized by blue to blue litmus paper and flame. DCM, Phenol and benzoic acid are both
red to red litmus paper. non-flammable.
As shown in the table, phenol is acidic
while ethylamine is basic and Ethanol is a neutral Though the IR Spectrometry Test was not
sample. This results prove further that the performed, it is important to know some
solubility of ethanol in Sodium hydroxide shown important concepts that can be retrieved from
in Table 3 indicates the presence of acid, and the this kind of test. The position of the bond
solubility of ethylamine in hydrochloric acid depends upon a number of characteristics of a
indicates the presence of a base. bond. The higher the bond order, the higher the
Cyclohexane, DCM and benzoic acid were wave number for the stretching vibration for a
not subjected to the litmus paper test because of bond. So in terms of degree of luminosity,
their immiscible/insoluble property with water. aromatic compounds will have the greatest
length, followed by unsaturated hydrocarbons,
Table 5. Behavior of Samples towards Ignition then the saturated hydrocarbons.
Organic Ignition Test and Type of Some of the data may not agree with each
Sample Flame Produced other, this may be because of some
experimental, and personal errors or the
Cyclohexane Flammable - Luminous flame
uncleanliness of some apparatus which may lead
DCM Non-flammable to contamination and results to wrong data.
Ethanol Flammable - Non-luminous
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