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Advanced Organic Chemistry: Mass spectrum of 1,4-dimethylbenzene

The mass spectrum of 1,4-dimethylbenzene

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 1,4-dimethylbenzene

C8H10 mass spectrum of 1,4-dimethylbenzene fragmentation pattern of m/z m/e ions for analysis and identification of p-xylene image diagram doc brown's advanced organic chemistry revision notes 

1,4-dimethylbenzene, C6H4(CH3)2 ,C8H10, (c) doc b , (c) doc b

Interpreting the fragmentation pattern of the mass spectrum of 1,4-dimethylbenzene

[M]+ is the molecular ion peak (M) with an m/z of 106 corresponding to [C8H10]+, the original 1,4-dimethylbenzene molecule minus an electron, [C6H4(CH3)2]+.

The small M+1 peak at m/z 107, corresponds to an ionised 1,4-dimethylbenzene molecule with one 13C atom in it i.e. an ionised 1,3-dimethylbenzene molecule of formula 13C12C7H10O

Identifying the species giving the most prominent peaks (apart from M) in the fragmentation pattern of 1,4-dimethylbenzene.

m/z value of [fragment]+ 105 91 79 78 77 65 63 51 39
[molecular fragment]+ [C8H9]+ [C7H7]+ [C6H7]+ [C6H6]+ [C6H5]+ [C5H5]+ [C5H3]+ [C4H3]+ [C3H3]+

Analysing and explaining the principal ions in the fragmentation pattern of the mass spectrum of 1,4-dimethylbenzene

Equations to explain the most abundant ion peaks of 1,4-dimethylbenzene

Formation of m/z 105 ion: [C6H4(CH3)2]+  ===>  [C8H9]+  +  H

Quite an abundant ion, formed by proton loss from the parent molecular ion.

Formation of m/z 91 ion: [C6H4(CH3)2]+  ===>  [C7H7]+  +  CH3

The m/z 91 ion is the base peak ion, the most abundant and 'stable' ion fragment, formed by the loss of a methyl group (106 - 15 = 91).

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 1,4-dimethylbenzene.


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