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Advanced Organic Chemistry: Mass spectrum of (1-methylethyl)benzene (cumene)

The mass spectrum of (1-methylethyl)benzene (2-phenylpropane, cumene)

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-methylethyl)benzene (cumene)

C9H12 mass spectrum of (1-methylethyl)benzene (cumene) fragmentation pattern of m/z m/e ions for analysis and identification of 2-phenylpropane cumene image diagram doc brown's advanced organic chemistry revision notes 

 (1-methylethyl)benzene, 2-phenylpropane, C9H12 , C6H5CH(CH3)2 , , (cumene)

Interpreting the fragmentation pattern of the mass spectrum of (1-methylethyl)benzene (cumene)

[M]+ is the molecular ion peak (M) with an m/z of ? corresponding to [C9H12]+, the original (1-methylethyl)benzene (cumene) molecule minus an electron, [C6H5CH(CH3)2]+.

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

Identifying the species giving the most prominent peaks (apart from M) in the fragmentation pattern of (1-methylethyl)benzene (cumene).

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

Analysing and explaining the principal ions in the fragmentation pattern of the mass spectrum of (1-methylethyl)benzene (cumene)

Equations to explain the most abundant ion peaks of (1-methylethyl)benzene (cumene)

Formation of m/z 105 ion: [C6H3CH(CH3)2]+  ===>  [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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