Identification of Unknown Organic Compounds by Melting Point, Boiling Point and

Infrared Spectroscopy
Riyushi Mahadik
January 30, 2014

Methods and Background

Solid sample K
Isatin (C8H5NO2)
M.P. 203C, 147.13 g/mol

Liquid sample L
Ethyl acetate (C4H8O2)
B.P. 77C, 88.11 g/mol
Figure 1.

The purpose of this lab is to determine the unknown solid and liquid samples through different
techniques. These techniques include the physical properties of the sample that are melting point
of the solid sample K and boiling point of the liquid sample L. The Infrared spectroscopy is used
to determine the number of functional groups and identify possible compound of the samples.
From the elemental analysis, the molecular and empirical formulas are derived for the unknowns.
Infrared (IR) Spectroscopy doesnt provide with chemical composition or quantitative data rather
it provides the peaks at certain wavenumber indicating the carbon to carbon double/triple bonds,
aromatic rings, carbonyl groups, or hydroxyl groups. IR uses the wavenumber in cm-1 which
provides direct relationship between energy and wavenumber and also proves the Hookes law.
IR measures the light transmitted by the sample than absorption. The lower % transmittance, the
greater is the absorption of light. The device used in this experiment is Attenuated Total
Reflectance (ATR) FT-IR accessory that creates graphs with peaks indicating specific functional
groups in unknown.
Melting and boiling points techniques are used to figure out the physical properties of the
samples. To determine the melting point of solid sample, the sample was inserted in Mel-Temp
apparatus that melts the sample and determines the temperature on the thermometer. The melting
point of the unknown sample is then compared to hypothetical values of other compounds that
share the same physical properties. Similarly, the boiling point apparatus was set up known as
miniscale method in which the liquid is boiled, and the temperature is noted on the thermometer.
The results from the apparatus are then compared to other known boiling point values of

compounds.
Index of Hydrogen Deficiency (IHD) is used to determine the number of double/triple bonds or
rings in the unknown samples. IHD values can be derived from the molecular formula. This
helps us predict correct compound along with the physical properties of that compound.
After analyzing the collected data and hypothetical values, the unknown samples K and L
indicated the compounds as Isatin and Ethyl acetate respectively (Figure 1.)
Experimental Procedure(s)
For the melting point of solid sample K, solid sample was added in a capillary tube to the end,
and the temperature was dropped to 50C before starting the experiment. Then, the switch of the
Mel-Temp device was turned on, and the capillary tube was inserted in the device. The heating
level was changed to six. The temperature was recorded when the whole sample was melted.
After recording the data, the capillary tube was disposed, and the device was switched off.
For the IR of the unknowns, the surface of the apparatus was cleaned with Q-tip and acetone.
Particularly, the silver disc and knob was cleaned properly. The background scan was taken and
was compared to the spectrum of the standard. After matching the standard, the thin film of solid
sample was placed onto the center of the disc using the Q-tip. Then, the knob was swiveled and
turned to the sample so the clamp is tightly covering the solid sample. The commands were
followed on the computer in order to find the peaks on the graph which was printed. Again, the
disc and the knob were cleaned with Q-tip, and acetone and the black disc was placed on the
middle of apparatus. The liquid sample up to five drops was added to the black disc, and the
black top was covered. Again, the commands were followed on the computer to figure out the
peaks on the graph of liquid sample which was printed out.
For boiling point of liquid sample L, apparatus was set up and the thermometer was placed 20
cm above the 1 ml surface of liquid in a test tube. One boiling stone was added to the test tube.
The liquid was boiled vigorously and temperature was recorded at that time.

Data Acquisition/Presentation
I. Relevant Equations
Conversion of wavenumber to wavelength: Wavenumber ( cm-1) = 10,000/
^ = where:
Hookes Law for simple harmonic oscillators:

= frequency of absorption in cm

-1

c
= speed of light

k
= force constant of bond

m
* = reduced mass of atoms joined by

bond =
Percent transmittance:%T = I/Io * 100 where:
I-intensity of radiation
transmitted through sample at a particular wavelength
Io- intensity of
radiation incident an sample at some wavelength.
IHD from molecular formula

IHD = (CnHxOy)

IHD = (CnHxNy)

IHD = (CnHxXy)
II. Datatables
Table 1. Table of Elemental Analysis and Molar Mass
Unknown

Carbon (C)

Hydrogen (H) Oxygen (O)

Nitrogen (N)

Molar mass
(g/mol)

K (solid)

65.32%

3.43%

21.75%

9.52%

147.032

L (liquid)

54.53%

9.15%

36.32%

0%

88.052

Table 2. Summary of Chemical Composition and Physical Properties Obtained from

Calculations and Procedure Respectively
Unknown

MP/BP ( C)

Molecular Formula

IHD

K (solid)

MP- 195-196

C8H5NO2

L (liquid)

BP- 75

C4H8O2

Calculation One: Solid Sample K

Molecular Formula Determination
Convert percentages of elements into grams. Convert grams to moles using molecular weight.
Divide all elements by lowest moles. Divide molecular weight by empirical molecular weight.

Multiple that number by empirical formula to get molecular formula.

= 5.437 mol= = 8

Hydrogen (H) = 3.43% = 3.43 g = 3.396 mol= = 5

Oxygen (O)= 21.75% = 21.75 g = 1.359 mol= = 2

Nitrogen (N)= 9.52% = 9.52 g = 0.679 mol= = 1

Carbon (C) = 65.32% = 65.32 g

Empirical Formula- C8H5NO2 (147.10 g/mol)

Molar mass (g/mol)= 147.032
147.10 g/mol/147.032 g/mol= 1
Molecular Formula= 1(C8H5NO2 ) = C8H5NO2
IHD Determination- C8H5NO2
= =7

Fourier Transform Infrared Spectroscopy

Peaks at 3188.12 cm-1 indicates the N-H group (3300-3450 cm-1 )
Peaks 1724.33 and 1612.83 cm-1 indicates two C=O bonds (1750-1735 cm -1)
Peaks from 1459.16 to 1329.93 cm-1 indicates benzene ring structure (1500-1400 cm-1)
Hypothetical Structures
Isatin

Melting Point Determination

The data recorded from the experiment was 195-196C
Structure Elucidation
The melting point of Isatin is 203 C which is similar to the melting point of experimental data.
Thus, the unknown solid sample K is Isatin.
Calculation Two: Liquid Sample L
Molecular Formula Determination
Convert percentages of elements into grams. Convert grams to moles using molecular weight.
Divide all elements by lowest moles. Divide molecular weight by empirical molecular weight.

Multiple that number by empirical formula to get molecular formula.

Carbon (C) =54.53%= 54.53g =4.54 mol= = 2

Hydrogen (H) = 9.15% = 9.15g =9.15mol= = 4

Oxygen (O) = 36.32% = 36.32g =2.26mol = = 1

Nitrogen (N) = 0 % = 0
Empirical Formula- C2H4O (44.43 g/mol)
Molar mass (g/mol) =88.052
88.052 g/mol/44.43 g/mol = 2
Molecular Formula= 2(C2H4O ) = C4H8O2
IHD Determination -C4H8O2
= =1

Fourier Transform Infrared Spectroscopy

Peaks at 2984.05 cm-1 indicates the C-H stretching (3000-2840 cm-1 )
Peaks at 1736.84 cm-1 indicates one C=O bond ester (1750-1735 cm-1)
Peaks at 1447.62 cm-1 indicates C-H bending (1475-1430 cm-1)
Hypothetical Structures

Ethyl acetate
(or)

Boiling Point Determination

The data recorded from the experiment was 75C.
Structure Elucidation
The boiling point of Ethyl acetate is 77 C which is similar to the boiling point of experimental
data. Thus, the unknown liquid sample L is Ethyl acetate.

Conclusion
The goal of the experiment was to determine and identify the unknown solids and liquids
through different experiments such as melting point, boiling point and IR. The unknowns were
solid sample K and liquid sample L which were analyzed using the IR. The molecular formula
for solid sample K is C8H5NO2 and IHD is 7. Thus, after looking over the IR the frequency at
3188.12 cm-1 indicates the N-H group (3300-3450 cm-1 ) in the compound. The other possible
functional groups could be two C=O bonds (1750-1735 cm -1) at 1724.33 and 1612.83 cm-1 . The
third possible functional group in the solid sample will be Benzene ring structure (1500-1400 cm1
) indicating peaks from 1459.16 to 1329.93 cm-1. The solid sample melted completely around
195-196C which is almost identical or near to the melting point of Isatin. The melting point of
Isatin is 203 C and the molecular formula is similar to the unknown solid sample. In the
structure of Isatin, there are two rings, and five double bonds indicating IHD of 7. Thus, this
indicates the unknown solid sample K is Isatin.
The molecular formula for liquid sample L is (C4H8O2) and IHD is 1. Thus, after looking over the
IR the frequency at 2984.05 cm-1 indicates the C-H stretching (3000-2840 cm-1 ) in the
compound. The other possible functional group could be one C=O bond ester (indicate the
numbers) at 1736.84 . The third possible functional group in the liquid sample will be C-H
bending (1475-1430 cm-1) indicating peak at 1447.62cm-1. The liquid sample boiled at 75C
which is almost identical or near to the boiling point of Ethyl acetate. The boiling point of Ethyl
acetate is 77 C and the molecular formula is similar to the unknown liquid sample. In the
structure of Ethyl acetate, there are one double bond indicating IHD of l. Thus, this indicates the
unknown liquid sample L is Ethyl acetate.
The experiment was successful because the prediction made about the compound through
molecular formula and IHD calculations matches with the data calculate from the experiments.
This means the data from the IR and melting and boiling points are helpful to determine the
compound with same molecular formula and IHD.
The problems that might arise with the boiling point procedure are that the level of heat should
be increased if the liquid doesnt boil. The sample didn't boil, so the experiment was repeated in
order to achieve desired results. The reason that could cause this can be contaminated liquid
sample or bad thermometer. One of the challenges that can be occurred in IR apparatus is that if
there is not enough sample in the black disc than the apparatus will not create graph of the
sample. The experiment was done again after adding more of the liquid sample to the disc.
Reference
Gilbert, J.C., Experimental Organic Chemistry, Cengage Learning, Boston, 2011, 5th Ed, pp. 41,
237-256.