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Advanced Organic Chemistry: Mass spectrum of benzene C6H6

Mass spectrum of benzene C6H6

Doc Brown's Chemistry Advanced Level Pre-University Chemistry Revision Study Notes for UK IB KS5 A/AS GCE advanced A level organic chemistry students US K12 grade 11 grade 12 organic chemistry courses involving molecular spectroscopy analysing mass spectra of benzene

image diagram mass spectrum of benzene fragmentation pattern of ions for analysis and identification of benzene  doc brown's advanced organic chemistry revision notes 

aromatic benzene C6H6, skeletal formula (c) doc b , structural/displayed formula

Interpreting the mass spectrum of benzene C6H6

[M]+ is the molecular ion peak (M) with an m/z of 78 corresponding to [C6H6]+, the original molecule minus an electron.

The small M+1 peak at m/z 79, corresponds to an ionised benzene molecule with one 13C atom in it i.e. an ionised molecule of formula [13C12C5H6]+

Carbon-13 only accounts for ~1% of all carbon atoms (12C ~99%), but the more carbon atoms in the molecule, the greater the probability of observing this 13C M+1 peak.

Benzene has 6 carbon atoms, so on average, ~1 in 17 molecules will contain a 13C atom.

The most abundant ion of the molecule under mass spectrometry investigation (benzene) is usually given an arbitrary abundance value of 100, called the base ion peak, and all other abundances ('intensities') are measured against it.

In this case the base peak ion is also the molecular ion of benzene itself [C6H6]+

Identifying the species giving the most prominent peaks (apart from M) in the fragmentation pattern of benzene.

Unless otherwise indicated, assume the carbon atoms in benzene are the 12C isotope.

Some of the possible positive ions, [molecular fragment]+, formed in the mass spectrometry of benzene.

The parent molecular ion of benzene m/z 78: [C6H10]+

Data table of some of the ions formed in the fragmentation pattern of the mass spectrum of benzene

m/z value of [fragment]+ 78 77 76 74 52 51 50 39
[molecular fragment]+ [C6H6]+ [C6H5]+ [C6H4]+ [C6H2]+ [C4H4]+ [C4H3]+ [C4H2]+ [C3H3]+

Explaining the principal fragments

Possible equations to explain some of the most abundant ion peaks in the mass spectrum of benzene (tabulated above)

Atomic masses: H = 1;  C = 12 (13 for ~1 in 100)

Bond enthalpies = kJ/mol: = 518 (benzene ring);  C-H = 412

The 'phenyl' fragment m/z 77 is formed by the loss a proton from the molecular ion.

[C6H6]+  ===>  [C6H5]+  +  H

Mass change 78 - 1 = 77

This 'phenyl' fragment is very indicative of the presence of a benzene ring in the molecule.

The m/z 77 ion can further lose a hydrogen atom/molecule to give m/z ions of 76, 75, 74 and 73.

The molecular m/z 78 ion itself could lose a hydrogen molecule to give the m/z 76 ion.

The m/z ions 50 to 52

These involve the loss of an unionised two carbon fragment to give a C4 fragment ion e.g.

[C6H6]+  ===>  [C4H4]+  +  C2H2

The m/z 39 ion

This is a common fragment in many organic spectra (I think its a triangle with a delocalised system stabilising the positive charge).

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Associated links

The infrared spectrum of Benzene

The H-1 NMR spectrum of Benzene

The C-13 NMR spectrum of Benzene

The chemistry of AROMATIC COMPOUNDS revision notes INDEX

Mass spectroscopy index


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