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Advanced Organic Chemistry: Mass spectrum of butanone

The mass spectrum of butanone

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 butanone (2-butanone, butan-2-one)

mass spectrum of butanone fragmentation pattern of m/z m/e ions for analysis and identification of  2-butanone butan-2-one image diagram doc brown's advanced organic chemistry revision notes 

Butanone C4H8O,  aldehydes and ketones nomenclature (c) doc b , aldehydes and ketones nomenclature (c) doc b , aldehydes and ketones nomenclature (c) doc b , aldehydes and ketones nomenclature (c) doc b

Interpreting the fragmentation pattern of the mass spectrum of butanone

[M]+ is the molecular ion peak (M) with an m/z of 72 corresponding to [C4H8O]+, the original butanone molecule minus an electron, [CH3COCH2CH3]+.

The small M+1 peak at m/z 73, corresponds to an ionised butanone molecule with one 13C atom in it i.e. an ionised butanone molecule of formula 13C12C3H8O

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

m/z value of [fragment]+ 57 43 29 28 27 15
[molecular fragment]+ [CH3CH2CO]+ [CH3CO]+ [CH2CH3]+ [C2H4]+ [C2H3]+ [CH3]+

Explaining the principal fragments of the mass spectrum of butanone

Several of the most abundant ion peaks arise from scission of C-C bonds in the original molecular ion of butanone.

Formation of m/z 43 ion: [CH3COCH2CH3]+  ===>  [CH3CO]+  +  CH2CH3

The m/z 43 ion is the base peak, the most stable ion fragment.

Formation of m/z 57 ion: [CH3COCH2CH3]+  ===>  [CH3CH2CO]+  +  CH3

Formation of m/z 29 ion:  [CH3COCH2CH3]+  ===>  [CH2CH3]+  +  CH3CO

Formation of m/z 15 ion: [CH3COCH2CH3]+  ===>  [CH3]+  +  CH3CH2CO


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