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Mass Spectra and IR: 7A Mass Spectrometry Measuring The M of An Organic Molecule

Mass spectrometry and infrared spectroscopy are techniques used to analyze organic molecules. (1) Mass spectrometry works by breaking molecules into fragments when passed through the instrument, producing a series of peaks corresponding to the fragments. The peak with the highest mass/charge ratio corresponds to the intact molecular ion. (2) Infrared spectroscopy analyzes the vibrations of bonds in molecules. Different bonds including C=O, C-H, and O-H absorb at characteristic wavelengths that can be used to determine functional groups. (3) Both techniques provide information about molecular structure and bonding that can be used to identify unknown compounds.

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34 views3 pages

Mass Spectra and IR: 7A Mass Spectrometry Measuring The M of An Organic Molecule

Mass spectrometry and infrared spectroscopy are techniques used to analyze organic molecules. (1) Mass spectrometry works by breaking molecules into fragments when passed through the instrument, producing a series of peaks corresponding to the fragments. The peak with the highest mass/charge ratio corresponds to the intact molecular ion. (2) Infrared spectroscopy analyzes the vibrations of bonds in molecules. Different bonds including C=O, C-H, and O-H absorb at characteristic wavelengths that can be used to determine functional groups. (3) Both techniques provide information about molecular structure and bonding that can be used to identify unknown compounds.

Uploaded by

asda.
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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7.

Mass spectra and IR


7A Mass spectrometry

Measuring the Mr of an organic molecule


Spectra for C4H10

If a molecule is put through a mass spectrometer Mass spectrum for


it will often break up and give a series of peaks butane
caused by the fragments. The peak with the
largest m/z, however, will be due to the complete Molecular ion
43 CH+
4 10
molecule and will be equal to the Mr of the
molecule. This peak is called the parent ion or 29
molecular ion
58

Fragmentation
Molecular ion formed:M → [M]+. + e–
When organic molecules are passed through a
mass spectrometer, it detects both the whole The molecule loses an electron and becomes both an ion and a free radical
molecule and fragments of the molecule.

Several peaks in the mass spectrum occur due to fragmentation. This process produces an
The molecular ion fragments due to covalent bonds breaking: [M]+. → X+ + Y. ion and a free radical. The
ion is responsible for the
Relatively stable ions such as carbocations R+ such as CH3CH2+ and peak
acylium ions [R-C=O]+ are common. The more stable the ion, the greater
the peak intensity.

The peak with the highest mass/charge ratio will be normally due to the original molecule that hasn’t fragmented (called the molecular

Equation for formation molecular ion


Mass spectrum for propanal
CH3CH2CHO  [CH3CH2CHO]+. + e– m/z 58
29 [CHO]+
Equations for formation of fragment ions from molecular ions

58 [CH3CH2CHO]+. [CH3CH2CHO]+.  [CHO]+ + .CH2CH3 m/z 29

[CH3CH2CHO]+.  [CH3CH2]+ + .CHO m/z 29

Equation for formation molecular ion


Mass spectrum for propanone CH COCH  [CH COCH ]+. + e– m/z 58
3 3 3 3
43acyl group
The high peak at 43 due to stability of
[CH3CO]+ Equations for formation of fragment ions from molecular ions

[CH3COCH3]+. [CH3COCH3]+.  [CH3CO]+ + . CH3 m/z 43


58
15 It is not possible for propanone to fragment to give a peak at 29 so the frag

N Goalby chemrevise.org 1
7B Infrared spectroscopy

a molecule absorb infra-red radiation at characteristicComplicated


frequenciesspectra
causingcan
thebe obtained
covalent thantoprovide
bonds vibrateinformation about the types of bonds prese

ABOVE 1500 cm-1 – “Functional group identification”


BELOW 1500 cm-1 – “Fingerprinting”

Complicated and contains many signals – picking out functional group signals d

This part of the spectrum is unique for every compound, and so can be used as

e.g. C=O 1640 – 1750 cm-1 A computer will compare the IR spectra against a database of known pure compounds t
O-H (acid) 2500- 3300 cm-1

Use an IR absorption table provided in


exam to deduce presence or absence
of particular bonds or functional
groups
Use spectra to identify particular functional groups e.g. an alcohol from
Bond Wavenumber an absorption peak of the O–H bond, or C=O stretching absorption in
aldehydes and ketones
C-O 1000-1300

C=O 1640-1750 Spectra for


butanal
C-H 2850 -3100

O-H 2500-3300 O
Carboxylic acids Very broad H3C CH2 CH2 C
H
N-H 3200-3500

O-H 3200- 3550 2000 1500


Acohols, phenols broad C=O
Absorption or trough in between 1640-1750 cm -1 range indicates
presence of C=O bond
Always quote the wave number range from the data sheet

Spectra for
O-H absorptions ethanoic acid
tend to be broad
O
Absorption or trough in
between 2500-3300 cm-1 range H 3C C
indicates presence of O-H OH
bond in an acid

C=O
Absorption or trough in between 1640-
1750 cm-1 range indicates presence of
C=O bond

olecules which change their polarity as they vibrate can absorb infrared radiation. E.g. C-H, C=O, O-H

H2, O2 and N2 cannot change their polarity as they vibrate so can absorb infrared radiation and don’t register on an infra red spectrum

n by bonds in this type of spectroscopy is the same absorption that bonds in CO2, methane and water vapour in the atmosphere do that cause them

O, CO2, CH4 and NO molecules absorb IR radiation and are greenhouse gases, whilst O2 and N2 are not.

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