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COMPARATIVE INVESTIGATION OF ORGANIC COMPOUNDS

Bettina Maria Q. Acuna, Enrico Joseph C. Aguinaldo, Alyanna Patrice


L. Arceo,
Jasmine Grace C. Asinas and Sigrid Jessa R. Bello
Group 1 2G Pharmacy Organic Chemistry Laboratory


ABSTRACT
The experiment was conducted in order to differentiate organic compounds in terms of certain
intrinsic physical properties, solubility and miscibility, acidity and basicity and behavior
towards ignition test. Physical properties are noted 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. Acidity and basicity of the
compounds were determined by the use of litmus paper. Ignition test was conducted using 3
to 5 drops of the sample in an evaporating dish and lighting it with a match.



INTRODUCTION
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.
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 (functional group). 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 by using infrared spectroscopy.
Organic compounds have different physical properties, which are intrinsic
or (characteristic of the class), such as odor. The physical state of an
organic compound at room temperature may indicate the strength of
interactive forces that exist between its molecules. The dissolution of
organic compounds in certain solvents may involve physical or chemical
interaction. Water solubility of these compounds may differ due to their
varying polarities. Solubility in acids or bases leads to more specific
information about the compound, i.e., as having either acidic or basic
property. Miscibility is the ability of two liquids to mix with each to form a
homogeneous solution.
Flammability is tested through an ignition test. Ignition of the organic
compound brings about a chemical change. Some organic compounds
decompose and blacken (charring), while other burst into flames.

Condensed structural formula of the compounds used:

Cyclohexane








DCM

CH
2
Cl
2


Ethanol



Phenol


Benzoic acid


Ethyl acetate


Ethylamine




EXPERIMENTAL
Compounds tested (or Samples used)
Cyclohexane, Dichloromethane, Ethanol, Phenol, Benzoic acid,
Ethyl Acetate, Ethylamine

Procedure
Physical State, Color and Odor
The physical state of the sample was observed in room
temperature. Color and odor was noted.

Solubility Properties
The samples were introduced into clean and dry test tubes. 4
drops of each sample were introduced if the sample is a liquid; and
0.1g 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 3mL. Any color changes, warming or
effervescence, soluble/insoluble, miscible/immiscible were noted.

Reaction with Litmus Paper
Drops of the sample tested its aqueous solution with red and
blue litmus papers. Color changes with both litmus papers were
noted.

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 was also noted


RESULTS AND DISCUSSION
Most of the hydrocarbons were colorless, but due to oxidation, some
compound showed a change in color, such as Phenol giving a red-orange
color. The odors of the compounds were quite similar but it has its unique
differences. Solubility properties of organic compounds using water,
5%NaOH solution and 5%HCl solution whether the samples are
soluble/insoluble or the samples are miscible/immiscible. Based on the
results, Cyclohexane is miscible in water, slightly miscible in 5%NaOH and
5%HCl; DCM is 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 is immiscible in water and
5%NaOH, and it is miscible in 5%HCl. Reactions with litmus paper indicates
the acidity/basicity of water-soluble samples. If it is from Red to Blue,
result will be a base indicator and if it is from Blue to Red, result will be an
acid indicator. The Litmus paper that retains its color indicates a neutral
compound. Solubility of organic compound also indicates acidity and
basicity of the sample. The result of Ignition test indicates the presence of
unsaturated or high carbon to hydrogen ratio. 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 (nonluminous) and
there is more heat than light, the carbon is completely oxidized.

2 C
10
H
22
+ 31 O
2
20 CO
2
+ 2 H
2
O

Incomplete combustion is indicated by a yellow flame (luminous) and
there is much light than heat, the carbon is not completely oxidized.


REFERENCES
From the internet
http://www.lindane.org/chemicals/cyclohexane.htm 9/8/12

http://www.wisegeek.co
m/in-chemistry-what-is-miscibility.htm 9/8/12

http://www.wisegeek.com/what-are-organic-compounds.htm 9/8/12

From books
Bayquen, A.V., Cruz, C.T., De Quia, R.M., Lampa, F.F., Pena, G.T., Sarile, A.S.
and Torres P.C. (2009). Laboratory Manual in Organic Chemistry. Quezon
City: C and E Publishing, Inc.














































































Table 1. Comparative Investigation of Organic Compounds


Test
Compounds
Cyclohexane DCM Ethanol Phenol
Physical State
at RT
Liquid Liquid Liquid Liquid
Color Clear, colorless Clear, colorless Clear, colorless
Clear, red
(oxidized)
Odor Mild, sweet odor
Acetone-like
odor
Alcohol-like
odor
Paste-like odor
Solubility in
H
2
O

5% NaOH soln.

5% HCL soln.
Miscible Immiscible Miscible Miscible


Slightly miscible

Immiscible

Miscible

Miscible
Slightly miscible Immiscible Miscible Miscible
Reaction with
litmus paper
Neutral Neutral Neutral Neutral
Ignition test
Yellow,
luminous,
Non-flammable
Yellow,
luminous,
Yellow,
luminous,
flammable flammable flammable



Table 2. Comparative Investigation of Organic Compounds

Test Compounds Benzoic acid Ethyl Acetate Ethyl Amine
Physical State at RT Solid Liquid Liquid
Color Clear, colorless Colorless Clear,colorless
Odor Odorless Plastic balloon odor Fishy
Solubility in
H
2
O

5% NaOH soln.

5% HCL soln.
Miscible Immiscible Miscible


Slightly miscible

Immiscible

Miscible
Miscible Miscible Miscible
Reaction with
litmus paper
Acidic Neutral neutral
Ignition test Non-flammable
Yellow, luminous,
flammable
Non-flammable