Determining Acid-base Properties and Infrared Spectroscopic Analysis of Organic

Compounds
ABELLA, Angelica B. *
ADVIENTO, Audrey A. *
ARCANGEL, Nicholas Raphael P.
BALANI, Jesusa Christina M.
College of Science, University of Santo Tomas

Abstract
Five known samples were tested to determine their solubility and acid-base properties.
To do this, different amounts of other compounds were added to the samples. The
physical state and structure of the samples were determined. Additional samples of
known character were analyzed using Infrared Spectroscopy. The compounds were
labelled and characterized to the type of bonds present in them. Using the rubber
aspirator, air from the container of the samples were taken and tested using the IR
spectroscopy method. Graphs of frequency waves were analyzed and discussed.
Results showed the bonds present in every compound.

I.

Introduction
Organic compounds are the complex compounds of carbon. These compounds

are determined by their physical properties which includes flammability, solubility and
physical state. All of these properties are based on the molecular formula of a
compound. Furthermore, infrared spectroscopy analysis determines all of the functional
groups present on the sample.
Solubility tests are conducted to identify the major functional group of the
compound and its acidity or basicity. Compounds with similar properties, mainly polarity,
are soluble in each other. Likewise, compounds which have different properties are
insoluble with each other. However, if the organic compound is dissolved in the solvent

is a liquid, it is rather considered as miscible. Meaning, the solute is mixed

homogeneously in all proportions (Carey, 2000).
Acids and bases are generally described in two ways. First is using the BronstedLowry and the second is through Lewis reactions (Solomons, et al., 2014). Bronsted
acids are basically proton donors and its disassociation yields a proton and a conjugate
base. Bronzed base, on the other hand, are proton acceptors through accepting an
electron pair to form a bond with a proton. Second is through Lewis reactions. Lewis
acids is an electron acceptor and Lewis base is an electron donor. However, Lewis
acids includes the proton since protons accept electron pairs. Thus, Bronsted-Lowry
acids are a subset of Lewis acids (Hoffman, 2004).
Infrared spectroscopy is an absorption method in the wavelength region in the
region of 1 to 100 micrometers. The infrared radiation triggers vibrational and rotational
methods in molecules. It provides information about the presence or absence of
functional groups in a sample (Wade, 2003). Also, the energy at which any peak in an
absorption spectrum corresponds to the frequency emitted by the vibration of the
molecules of the sample.

II.

Methodology
Duplicate test tubes containing 10 drops of each organic sample (Isoamyl

acetate, Cyclohexane, Ethylamine, Ethanol, Phenol and Benzoic acid) was labeled
correctly for the physical properties. Accurate safety techniques were applied during the
observation of the physical state of each compound. The results were recorded. Next,
the solubility of each compound was examined in aqueous base (distilled water) using
20 drops of 2M NaOH and 6M HCl. Consequently, A microspatula of benzoic acid was
placed in a watch glass. Then, 10 drops of NaHCO3 was added. Effervesce was
observed and recorded. On the other hand, 10 organic samples were used for Infrared
spectroscopy analysis representing each functional group. Rubber aspirator is used to
collect the air from the container of the samples and tested using the IR spectroscopy
method. The resulting frequency waves graph were analysed.

III.

Results and Discussion

Table 1. Physical properties of organic samples

ORGANIC SAMPLE

PHYSICAL STATE

Isoamyl acetate

Colorless liquid
!

STRUCTURE

Cyclohexane

Colorless liquid

Ethylamine

Colorless liquid
!

Ethanol

Colorless liquid
!

Phenol

Red liquid

Benzoic acid

White solid

Color, odor, refractive index, density, solubility, melting point and boiling point
comprises and determines the physical properties of a compound. Each compound has
different physical properties than the other. It is often influenced by the structure of a
compound. In the experiment, 6 different organic compounds were used representing
each functional group.
Isoamyl acetate is an organic compound ester formed from isoamyl alcohol and
acetic anhydride or acid. It has a molecular formula of C7H14O2. Isoamyl acetate is a
colourless liquid that is oftenly used industrially to confer banana flavour.
Cyclohexane from the functional group alkanes (cyclic) with a molecular formula
of C6H12. It is a colourless liquid that resembles detergent due to its odor.
Ethylamine is a representative of the group amines which has a formula of
C2H5NH2. This colourless liquid has a strong ammonia-like odor.
Ethanol from alcohols which has a formula of C2H5OH. It is also a colourless
liquid that is flammable and often used as a fuel and for medicinal purposes.
Phenol is a red liquid and coming from the aromatic compound. It has a
molecular formula of C6H5OH.
Benzoic acid is a white, solid crystalline and a simple aromatic carboxylic acid. It
has a molecular formula of C7H6O2.
Table 2. Solubility/miscibility of organic compounds

ORGANIC
SAMPLE

H2O

2M NaOH

6M HCl

NaHCO3

Isoamyl acetate Immiscible

Immiscible

Immiscible

Cyclohexane

Immiscible

Immiscible

Immiscible

Ethylamine

Miscible

Miscible

Miscible

Ethanol

Miscible

Miscible

Miscible

Miscible

Phenol

Immiscible

Miscible

Immiscible

Miscible

Benzoic acid

Immiscible

Miscible

Immiscible

Miscible

The solubility of the compounds are determined by the molecular formula and the
polarity. The basic solubility rule likes dissolve likes is applied in this experiment.
In water, the process is responsible for the energy cost and gains. The
equilibrium constant and the strength of an acid or a base is based on the energy
balance of a reaction. Therefore, the reaction has an energy cost from the breaking of a
bond to the hydrogen and the separation charged caused by the ionization (Hoffman,
2004). It is clearly seen in the table that only ethylamine and ethanol is miscible in
water. The Nitrogen present in ethylamine imbalances the charge distribution of the
compound, thus allowing hydrogen dipole-dipole bond in water (Carey, 2000). Likewise,
the ethanol is also miscible in water because of the OH group. The strength of the
attraction of the OH group makes the ethanol miscible in water.
Phenols and benzoic (carboxylic) acids dissolve in NaOH producing watersoluble salts. Both compounds produce resonance conjugate bases, meaning, it is
merely a representation of what is left after an acid has donated a proton during
chemical reaction (Festin & Raquepo, 2014). The difference between the two is the
strength of the acidity. Phenols are weaker acids compared to carboxylic acids.
HCl-Soluble compounds are considered as an organic base. Thus, ethylamine
and ethanol is an organic base. These basic compounds readily dissolved in an acidic
solution because they form hydrochloride salts (Procedure for determining the solubility
of organic compounds, N.D.)
Compounds that dissolve in NaHCO3 are considered as strong acids. In phenols,
the substitution of an electron leaving group increases the acidity of the compound.
Benzoic acid dissolves in NaHCO3 through the formation of medium salt (Festin &
Raquepo, 2014).
The following figures shows the results obtained in the conduct of Infrared (IR)
Spectroscopy on the ten known samples.
Figure 1. Infrared spectroscopy result of Hexane (Sample A)

The presence of alkane bonds in hexane was proven due to the large curve with
its peak at 2941 cm-1. Another peak was recorded at 2877.56 cm-1. Frequency waves
with a peak ranging from 2850 to 2960 cm-1 is an alkane. Thus, sample A, according to
the result is an alkane.
Figure 2. Infrared spectroscopy result of Cyclohexane (Sample B)

Sample B, cyclohexane, was tested for it being an alkene. A peak ranging from
3020 to 3080 cm-1 proves a sample to be an alkene. According to the result, a peak was
recorded, at 3033.89cm-1, therefore, a double bond was present in the sample. Also,
since there are peaks at 2935 cm-1 and 28.59 cm-1, single bonds are also in sample B.
Thus, cyclohexane contains single and double bonds.
Figure 3. Infrared spectroscopy result of Ethanol (Sample C)

A peak at 3674 cm-1 determined the presence of an O-H bond in Sample C,

ethanol. Also, a very prominent peak at 2934 cm-1 proved that single bonds are present
in the compound.
Figure 4. Infrared spectroscopy result of Ethylamine (Sample D)

In figure 4, sample D exhibits a peak at 2953cm-1 telling us that single bonds are
present in the compound. However, another peak at 3345 cm-1 proves that a N-H bond
is also present. Thus, sample D is indeed an amine.
Figure 5. Infrared spectroscopy result of Toluene (Sample E)

The peak at 1600 cm-1 proves the presence of aromatic ring in Sample E or
toluene. Also, between 3020 to 3080 cm-1 tells us that alkenes are also present in the
compound.
Figure 6. Infrared spectroscopy result of Amyl acetate (Sample F)

According to the figure above, the very sharp peak located at 1764 cm-1 confirms
the presence of C=O in the compound. Amyl acetate is a representative of ester in this
experiment.
Figure 7. Infrared spectroscopy result of Acetic acid (Sample G)

Sample G or acetic acid exhibits a very sharp peak at 1732 cm-1 confirming the
presence of C=O bond in the compound. Another peak at 3581 cm-1 proves the
presence of O-H bonds. Thus, the sample is indeed a carboxylic acid.

Figure 8. Infrared spectroscopy result of Acetone (Sample H)

A very prominent peak at 1725 cm-1 tells us the presence of C=O bond on the
compound. In addition, sample H also contains single bonds because of peaks at 3015
cm-1 and 2946 cm-1. Thus, acetone is a representative of ketone.
Figure 9. Infrared spectroscopy result of Formaldehyde (Sample I)

C=O is present in sample I because of a peak at 1739 cm-1. Another peak at

2936 cm-1 proves the presence of single bonds. Thus, sample I or formaldehyde is a
very good representative of aldehyde.

Figure 10. Infrared spectroscopy result of Formamide (Sample J)

The last sample, formamide, has peaks at 1743 cm-1 and 3708 cm-1. These
readings prove that there is a C=O and N-H bonds present in the compound. Because
of this, we can conclude that formamide is a representative of amide.
IV. Conclusion
Physical properties are very essential in determining the unknown and
differentiating a compound from another. The structure determines the solubility and the
acid-base properties of a compound. For instance, the solubility test of suggests that
compounds with single bonds tend to have a stronger bonds compared to the other
compounds. On the other hand, infrared spectroscopy is useful in determining the
bonds present in an organic compound, also, it is an effective way determine the
functional groups in an unknown. However, it could not give the exact structure of a
certain compound, thus, further experimentations and tests should be conducted.
V.

References

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