There are more than 5 million organic compounds, the great majority of which are colourless liquids
or white solids. Identifying or at least characterising – determining some of its properties and features
– organic compounds is an important technique in the pharmaceutical industry, and in research
laboratories. Until the last forty years, chemical methods dominated this area, but they are now to a
great extent, supplanted by instrumental methods, particularly spectroscopic techniques.
This chapter concentrates on the application of spectroscopic techniques in the structure
determination of organic compounds. The instrumental aspects of these techniques are covered in
other chapters or in Applied Spectroscopy.
bromine
NaHCO3
DNP
Fehlings
Physical Parameters
This includes such things as melting point, boiling point, refractive index, density etc. These are
determined and compared to literature values. A close match to a complete set of literature values is
strong but not definite evidence for identification of a substance.
1. Identification of Organic Compounds
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1. Identification of Organic Compounds
O
H
H
Figure 1.1 shows a simple breakdown of the regions of the infrared spectrum.
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4000 2500 2000 1500 cm
Bonds to H Triple bonds Double bonds
C-H C≡C C=C
O-H C≡N C=O
N-H C=N
Functional group region Fingerprint region
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1. Identification of Organic Compounds
A correlation table (see Table 1.1) lists the important peaks for each common functional group,
allowing you to identify the presence of particular groups in a the spectrum of a compound. Figures
1.2-1.10 show the functional group region for selected examples of each type of functional group.
NOTE - Since C-O, C-N and C-X bonds do not yield distinctive peaks in the functional group region,
ethers, alkyl halides and tertiary amines and amides do NOT give specific characteristic IR functional
group peaks.
Figures 1.2-1.10 will be provided by your teacher in hardcopy form as the detail in the
spectra cannot be satisfactorily gained by scanning.
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1. Identification of Organic Compounds
(i)
(ii)
(iii)
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1. Identification of Organic Compounds
(iv)
(v)
(vi)
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1. Identification of Organic Compounds
(b) How would you distinguish between the following pairs of compounds by their IR
spectra, assuming you couldn’t compare them to standard spectra for fingerprint
matching?
(i) methylbenzene and cyclohexane
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