Comparative Investigation of Organic Compounds

Fame F. Mercado, Alvin Leo T. Morelos, Danica Rose B. Ocampo, Rowleene P. Palabay, Jonna O. Perey
Group 6 2A Medical Technology Organic Chemistry Laboratory

ABSTRACT
This formal report presents the comparative investigation of the different organic compounds and spectrometric
analyses. In some cases, certain intrinsic physical property of the different compounds is characterized by physical
and chemical properties in terms of structure and behavior. The physical state, color and odor were noted by simple
physical observation. Miscibility was tested by introducing drops of a sample whether if it is a liquid or a solid.
Flammability was tested by placing 3-5 drops of the liquid sample in a small evaporating dish and lighting it with a
match. Reacting with Litmus paper was used to determine if the sample is soluble in water. The effective result of the
components is based on differences in the physical properties of the compounds, or of their derivatives. The tests
were conducted to figure out what each compound showed presence of. After going all through the tests, the
compounds differ in water solubility due to their varying polarities, the solubility in acids or base leads to more specific
information about the compound and the different physical and chemical properties and determining by using the
infrared spectroscopy. In this laboratory experiment, these solutions will be put to the test.

Introduction yellow but less sooty. Infrared (IR) spectrometry

gives additional information about a compound’s
Organic compounds are the complex structure. In NMR spectrometry, the relationship
compounds of carbon. Because carbon atoms of carbons and hydrogen to each other is
bond to one another easily, the basis of most determined. IR spectrometry aids in the
organic compounds is comprised of carbon chains identification of functional groups. In this
that vary in length and shape. Hydrogen, experiment, we will be able to determine and
nitrogen, and oxygen atoms are the most differentiate the compounds in terms of certain
common atoms that are generally attached to the intrinsic physical properties, behavior towards
carbon atoms. Each carbon atom has 4 as its ignition and the IR spectra of their functional
valence number which increases the complexity groups.
of the compounds that are formed. Since carbon
atoms are able to create double and triple bonds Condensed structural formula:
with other atoms, it further also raises the
likelihood for variation in the molecular make-up 1. Cyclohexane - Cycloalkane
of organic compounds. All hydrocarbons are
insoluble in water because of their relatively non-
polarity and easily distribute. When hydrocarbons
burn using oxygen, C02 and H20 are the sole
products. There are 2 large classes of
Hydrocarbon namely: Unsaturated and Saturated
hydrocarbons. Saturated Hydrocarbons are the
simplest type of organic compounds in which all
2. DCM – Halogenated
carbon-carbon bonds are single bonds. Example
CH2CL2
of Saturated Hydrocarbon is an alkane. On the
other hand, Unsaturated Hydrocarbons contains
one or more carbon-carbon multiple bonds like 3. Ethanol – Alcohol
double bonds and triple bonds. These 2 classes
have similar physical properties but differ in
chemical properties. Miscibility is the property of
liquids to mix in all proportions therefore forming
a homogenous solution. Flammability is the
measure of the extent to which a material or a
substance will support combustion. This is tested 4. Phenol – Phenol
through ignition test. Vapor pressure is an
important parameter in determining the ease of
ignition of a substance or material. Substances
are determined by the characteristics of their
flame when they burn. Some compounds
produces yellow, sooty flame due to their high
carbon content. Some burn with flames that are
 5. Benzoic Acid – Carboxylic Acid 4. Ignition Test
3-5 drops of the liquid sample
and a pinch amount of solid were
placed in an evaporating dish and was
lighted using a match. Any flame
produced and observed was noted.

5. Infrared (IR) Analysis

6. Ethyl Acetate – Ester Used the appendix notes to
identify the type of principal bond
present in the sample compound that
may be observed in the IR spectra and
its wave number range.

RESULTS AND DISCUSSION

7. Ethylamine – Amine
Most of the hydrocarbons are colorless.
However, many liquid compounds oxidize when
they are stored for a long time. Often the
oxidation products are intensely colored. The
result of the experiment showed that Phenol
becomes red orange upon oxidation and white
crystals for benzoic acid. The odors of the
EXPERIMENTAL compounds are quite similar but still it has
different identity. Solubility properties of organic
A. Compounds Tested (or samples compounds using H20, 5% NaOH solution and 5%
used) HCL solution indicates whether the sample is
Cyclohexane, DCM, Ethanol, Phenol, soluble or insoluble and if the sample is miscible
Benzoic Acid, Ethyl Acetate and Ethyl Amine. and immiscible. Based on the results, Benzoic
acid was slightly soluble in H20; insoluble in 5%
B. Procedure NaOH solution and with 5% HCL solution because
1. Physical State, Color and Odor of the fact that Benzoic acid is a solid matter.
The physical states were While the rest of the compounds that are liquid
observed at room temperature. The namely Cyclohexane and DCM were immiscible
color and odor was noted. and immiscible for Phenol when added with 5%
HCL soln. As for Ethanol, Ethyl Acetate and
2. Solubility Properties Ethylamine when added with H20,HCL and NaOH
The sample was introduced in a it becomes miscible. Reactions with litmus paper
clean and dry test tube. 4 drops of indicate the acidity/basicity of the H20-soluble
each sample was added if the sample samples. If it is from Red to Blue the result will
is a liquid; and 0.1 g of sample was be a base indicator and if it is Blue to Red the
added if the sample is a solid. The result will be an Acid indicator. The Litmus paper
solid samples were grinded to increase that retains its color indicates a neutral
the surface area. The solvent was compound. Solubility of organic compounds in
added drop wise and counted the 5% NaOH also reveals the acidity and basicity of
number of drops of solvent added to a the sample. The results of the Ignition test
total of 3mL. Any change, warming indicates the presence of Unsaturated or high
effects, soluble/insoluble, miscible/ carbon to hydrogen ratio. The degree of
immiscible or effervescence was noted. luminosity can be assessed by the presence of
yellow flame and soot. The Aromatic compounds
3. Reaction with Litmus Paper burn with sooty flame due to the incomplete
Drops of the sample tested its combustion which causes the formation of an
aqueous solution with red and blue unburned carbon. In terms of degree of
litmus papers. Color changes in both luminosity: aromatic compound > unsaturated
litmus papers were noted. 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 + 22 H2O

Incomplete combustion is indicated by a

yellow flame (luminous) and there is much light
than heat; the carbon is not completely oxidized.

2C2H2 + 5O2 = 4CO2 + 2H2O + heat

For IR spectrometry, the position of the

band 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.

The IR spectrum can be broken down into

three major regions:
1. The functional group region (1600-4000
cm-1) is the region in which where
functional groups absorb. Most of these
absorptions are at least of moderate
intensity, and many are quite strong. It is
relatively free from overlap or other
interferences.
2. The fingerprint region (1000-1600 cm-1) is
often quite complex. It is used for band-
by-band comparison of the spectrum of a
known compound in order to identify the
compound. C-O stretching of alcohols
esters are easily assigned.
3. The Aromatic region (675-900 cm-1) is
used to identify the number and relative
positions of groups on a benzene ring. C-H
bonds occur in this region.

Overall, the experiment succeeded in

showing the certain intrinsic physical and
chemical properties of the compounds, the
behavior towards ignition and the infrared
spectra of their functional groups.
REFERENCES:
From books
Lambert, J., Shurvell,H.,Lightner D., Cooks G.
(1987) QD. Introduction to Organic Spectres.
New York: John Wiley & Sons, Inc.

Silverstein, R.M., Webster, F.X., Kiemle, D.J.

(2005) Spectrometric Identification of Organic
Compounds. USA: John Wiley & Sons, Inc

Shriner, R., Hermann, C.K.F., Morrill, Curtin, D.Y.

(1998) The Systematic Identification of Organic
Compounds. 7th ed. New York: John Wiley &
Sons, Inc.

University of Santo Tomas Department of

Chemistry (ed.). (2000). Organic Chemistry
Laboratory Experiments Part 1. (unpublished
manual based by the Department of Chemistry,
College of Science, University of Santo Tomas)

From the internet

Dee, S. Wise Geek
http://www.wisegeek.com/what-are-organic-
compounds.htm 08/25/10
Table.1 Comparative Investigation of Organic Compounds

Test Cyclohexane DCM Ethanol Phenol

Compounds
Physical State Liquid Liquid Liquid Liquid
at RT
Color colorless Colorless Colorless colorless
Odor Faint ether-like Acetone-like Strong, Paste-like odor
odor Odor pungent odor
Test Cyclohexane DCM Ethanol Phenol
Compounds
Solubilty in

H2 0 Immiscible Immiscible miscible miscible

5% NaOH soln Immiscible Immiscible miscible miscible
5% HCL soln Immiscible Immiscible miscible Immiscible
Reactions with Not Applicable Not Applicable Neutral Acidic
Litmus Paper
Ignition Test Orange Flame; Non- Yellow Flame; Non-
sooty Flammable sooty Flammable
Observed C-H Stretch C-Cl 580-780 C-O Stretch C-O Stretch
Principal IR 3000-2840 1230-1000 1230-1000
Peaks (cm-1) C-H Bond C-H Bond O-H Bond
1475-1350 1420-1340 1420-1340
C-C Stretch O-H Stretch O-H Stretch
1200-800 3700-3100 3700-3100

Table 2. Comparative Investigation of Organic Compounds

Test Compounds Benzoic Acid Ethyl Acetate Ethylamine

Physical State at Solid Liquid Liquid
RT
Color White crystals Colorless Colorless
Odor Fetid, Urinous color Plastic balloon-like Ammonia-Like
Odor Odor
Solubilty in
H2 0 Slightly soluble Miscible Miscible
5% NaOH soln Insoluble Miscible Miscible
5% HCL soln Insoluble Miscible Miscible
Reactions with Acidic Neutral Basic
Litmus Paper
Ignition Test Non-Flammable Orange Flame; not Orange Flame; not
sooty sooty
Observed O-H stretch C=O Stretch N-H Stretch
Principal IR 3300-2500 1740-1210 3500-3300 &
Peaks (cm-1) C-O Stretch C-O Stretch 3400-3200
1730-1680 1245-1190 N-H Bond
O-H Bond 1640-1560
1440-1390 N-H Bond
C-O Stretch 900-650
1320-1210 C=N Stretch
1330-1030