Advanced Organic Chemistry: Mass spectrum 1,3,5-trimethylbenzene (mesitylene)

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The mass spectrum of 1,3,5-trimethylbenzene (mesitylene)

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 1,3,5-trimethylbenzene (mesitylene)

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Mass spectroscopy - spectra index

C9H12 mass spectrum of 1,3,5-trimethylbenzene mesitylene fragmentation pattern of m/z m/e ions for analysis and identification of mesitylene image diagram doc brown's advanced organic chemistry revision notes 

structural formula 1,3,5-trimethylbenzene mesitylene molecular structure molecular formula C9H12 C6H3(CH3)3

Interpreting the fragmentation pattern of the mass spectrum of 1,3,5-trimethylbenzene (mesitylene, C6H3(CH3)3)

[M]+ is the molecular ion peak (M) with an m/z of 120 corresponding to [C9H12]+, the original 1,3,5-trimethylbenzene (mesitylene) molecule minus an electron, [C6H3(CH3)3)]+.

The small M+1 peak at m/z 121, corresponds to an ionised 1,3,5-trimethylbenzene (mesitylene) molecule with one 13C atom in it i.e. an ionised 1,3,5-trimethylbenzene (mesitylene) molecule of formula 13C12C8H12

Identifying the species giving the most prominent peaks (apart from M) in the fragmentation pattern of 1,3,5-trimethylbenzene (mesitylene).

m/z value of [fragment]+ 105 91 79 77 65 51 41 39
[molecular fragment]+ [C8H9]+ [C7H7]+ [C6H7]+ [C6H5]+ [C5H5]+ [C4H3]+ [C3H5]+ [C3H3]+

Analysing and explaining the principal ions in the fragmentation pattern of the mass spectrum of 1,3,5-trimethylbenzene (mesitylene)

Equations to explain the most abundant ion peaks of 1,3,5-trimethylbenzene (mesitylene)

Formation of m/z 105 ion: [C6H3(CH3)3)]+  ===>  [C8H9]+  +  CH3

The m/z 105 ion is the base peak ion, the most abundant and 'stable' ion fragment, formed by the loss of a methyl group from the parent molecular ion (120 - 15 = 105).

The formation of the m/z 77 ion: [?]+  ===>  [C6H5]+  +  ?

This is a phenyl cation and very characteristic in the mass spectrum of aromatic benzene compounds like 1,3-dimethylbenzene.

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