May 16, 2021
SPECTROSCOPIC
IDENTIFICATION OF
ORGANIC COMPOUNDS 1
May 16, 2021
Analytical Techniques
Aim:
• identify and characterize unknown substances
• identify impurities
• determine the composition of a mixture
Types:
• qualitative
• quantitative
• structural - Different kinds of instruments are used. They
generally work by analyzing the effect of different forms of
energy on the substance analyzed (spectroscopy).
May 16, 2021
* Infrared spectroscopy- to identify the bonds in a molecule.
* Mass spectroscopy - to determine relative atomic and
molecular masses & to obtain evidence for the
arrangement of atoms in a molecule using the
fragmentation pattern.
* Nuclear magnetic resonance spectroscopy- to show the
chemical environment of certain isotopes ( hydrogen,
carbon, phosphorus, and fluorine) in a molecule.
May 16, 2021
measures the bond
Infrared Spectroscopy (IR) vibration frequencies
http://www.rsc.org/learn-chemistry/collections/spectroscopy/introduction#IRSpectroscopy
used to identify bonds and mainly the
functional group in a molecule
May 16, 2021
Mass Spectrometry
used to determine relative
atomic masses and
molecular masses and
fragmentation technique
gives evidence for the
arrangements of atoms in
a molecule
May 16, 2021
Nuclear Magnetic Resonance (NMR)
Indicated by how many groups of
How many types of H ?
signals there are in the spectra
Indicated by the chemical shift of each
What types of H ?
group
Indicated by the integration (relative
How many H of each type are there?
area) of the signal for each group.
Look at the coupling patterns. This tells
What is the connectivity ?
you what is next to each group
May 16, 2021
Mass Spectrometry https://www.youtube.com/watch?v=FbD5TTKGI-w&t=2
• used to find the mass of individual atoms and the relative
abundances of different isotopes
• used to find relative molecular mass of a compound (if the
empirical formula is known from compositional analysis,
the molecular formula can be determined)
In the mass spectrometer molecules are converted to
positive ions and these ions, after being accelerated
through an electric field are deflected by magnetic field.
By varying the magnetic field applied all ions reach the
detector. The mass spectrum records the relative
abundances of the fragments of different mass reaching
the detector.
May 16, 2021
May 16, 2021
Fragmentation Patterns
An electron from an electron gun hits the incident species
so energeticly that it causes the molecule to break up into
different fragments. Largest mass peak in the mass
spectrum corresponds to a parent ion which is formed
when the molecule loses one electron but otherwise
remains unchanged. The parent ion may also fragment into
smaller pieces and each fragment is deflected to a different
extent which appear as separate peaks on the spectrum.
The fragmentation pattern can be used for 'fingerprint'
purposes, but the mass of units that have broken off the
molecule will frequently give clues about the structure of the
molecule.
May 16, 2021
The structure of ethanol and its mass spectrum
possible fragmentation pattern
If the C - C bond breaks,
two outcomes are
possible.
May 16, 2021
Data Booklet : Table 28
May 16, 2021
Exercise:
May 16, 2021
Textbook: Page 552- 553
May 16, 2021
May 16, 2021
https://www.youtube.com/watch?time_continue=41&v=JsME_yd3ErI&feature=emb_logo
THE DEGREE OF UNSATURATION / INDEX OF
HYDROGEN DEFICIENCY (IHD)
It can be deduced from the molecular formula of an
organic compound. It is used to determine the amount of
unsaturation, i.e. the number of multiple bonds or rings in
the molecule.
It refers to the number of molecules of hydrogen,H2, that
would needed to be added to one molecule of an
unsaturated organic compound to make it saturated.
IHD = 2x + 2 - y /2
x = number of C atoms , y = number of H
atoms
May 16, 2021
May 16, 2021
May 16, 2021
May 16, 2021
The IHD values of some molecules
May 16, 2021
Textbook - Page 554
May 16, 2021
