Lab Report 6

Abstract
Lab 6 focused on the identification of an unknown compound. The purpose of the
lab was to deduce the structure of an unknown compound using spectroscopic
techniques, specifically infrared spectroscopy (IR), nuclear magnetic resonance
(NMR), and mass spectrometry (MS).

Introduction
One of the core concepts in organic chemistry is the identification of organic
structures. After extraction and purification, organic products are often confirmed
using spectroscopic techniques, which rely on measuring various types of
electromagnetic radiation absorbed or emitted by molecules. Infrared spectroscopy
(IR), nuclear magnetic resonance (NMR), and mass spectrometry (MS) are three of
the main techniques used for this purpose. IR is used to determine the functional
groups present in a compound, as each functional group absorbs specific
wavelengths of infrared radiation. Proton NMR is used to determine the structure
and chemical environment of the atoms in a molecule, as the positions and
strengths of NMR signals depend on the chemical environment of the nuclei. This
allows for peak identification based on chemical shift, integration, and multiplicity.
MS is used to determine the molecular weight and fragmentation pattern of a
compound. It also provides isotope data for compounds containing chlorine (75%
Cl-35/25% Cl-37) or bromine (51% Br-79/49% Br-81). Additionally, the C-13
isotope (1.1% natural abundance) can be analyzed through the M+1 peak to figure
out the number of carbons present in a compound. If the structure has already been
documented, the melting point can be used to confirm it. However, if the
compound is new, the melting point must be recorded for future comparison.

Results and Discussion

From the worksheet, the mass of the molecule (m/z) was reported to be 72. This
indicated that the compound had to be structured in such a way that a total of 72
would be obtained when the masses of all the elements in the compound were
added together. Since no additional information on mass spectroscopy was
provided, it was concluded that there were no chlorine or bromine atoms present in
the compound.

Figure 1. C Spectrum
13

Upon observation of figure 1, it was assumed that there were four distinct carbon
atoms resulting from the four signals in the spectrum. The first carbon at 202.2
ppm was presumed to be a carbonyl group. The second, third, and fourth carbons at
45.7 ppm, 15.5ppm, and 13.6 ppm respectively were presumed to be alkanes
ranging from R-CH3 to R4C in connectivity. Also, it was assumed that the
compound in question would be asymmetrical.
The compound was also reported to have displayed an IR peak at 1720cm-1. This
piece of information confirmed the presence of the carbonyl group also displayed
in the 13C spectrum, since carbonyl produces a peak between the range of 1650cm-1
- 1820cm-1.
The reported 1H NMR signals shown by the compound are displayed in table 1.
Using the proton NMR chemical shift chart, the appropriate molecules in terms of
chemical shift and connectivity were chosen. Also, the number of neighboring
protons were obtained by subtracting 1 from the multiplicity number, since
multiplicity is derived from the n + 1 formula.
Chemical shift Multiplicity Expected type of Number of
 (ppm) proton neighbor protons
0.98 Triplet 2
1.65 Sextet 5

2.38 Triplet 2

9.72 Singlet 0

Table 1. Information from 1H NMR signals

After combining the various pieces of information together, the structure deduced
was found to be butanal. As confirmation, the molar mass of the structure was
calculated as follows using the molar mass of carbon, hydrogen and oxygen.
Chemical formula = C4H8O, so (4*12) + (8*1) + 16 = 72g/mol

Figure 2. Butanal
Conclusion
The objective of lab 6 was accomplished. Infrared spectroscopy (IR), nuclear
magnetic resonance (NMR), and mass spectrometry (MS) were the spectroscopic
techniques used to the deduce the unknown compound. By using the key
information, such as molar mass, IR peaks, 13C signals, and 1H NMR signals,
provided by the different techniques, a conclusion about the unknown compound
was made. The unknown compound was found to be butanal with the chemical
formula of C4H8O. These techniques will be useful in the future when trying to
identify and confirm products as a result of multiple chemical pathways.