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Advanced Organic Chemistry: Mass spectrum of propylbenzene (1-phenylpropane)

The mass spectrum of propylbenzene (1-phenylpropane)

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 propylbenzene

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

propylbenzene, C9H12 , C6H5CH2CH2CH3 , (c) doc b  , (c) doc b 

Interpreting the fragmentation pattern of the mass spectrum of propylbenzene

[M]+ is the molecular ion peak (M) with an m/z of 120 corresponding to [C9H12]+, the original propylbenzene molecule minus an electron, [C6H5CH2CH2CH3]+.

The small M+1 peak at m/z 121, corresponds to an ionised propylbenzene molecule with one 13C atom in it i.e. an ionised propylbenzene molecule of formula 13C12C8H12

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

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

Analysing and explaining the principal ions in the fragmentation pattern of the mass spectrum of propylbenzene

Equations to explain the most abundant ion peaks of propylbenzene

Formation of m/z 105 ion: [C6H5CH2CH2CH3]+  ===>  [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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