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Advanced Organic Chemistry: Mass spectrum of butanal (butyraldehyde)

The mass spectrum of butanal

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 butanal

mass spectrum of butanal fragmentation pattern of m/z m/e ions for analysis and identification of butyraldehyde image diagram doc brown's advanced organic chemistry revision notes 

butanal (butyraldehyde), C4H8O,  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 butanal

[M]+ is the molecular ion peak (M) with an m/z of 72 corresponding to [C4H8O]+, the original butanal molecule minus an electron, [CH3CH2CH2CHO]+.

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

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

m/z value of [fragment]+ 71 57 44 43 43
[molecular fragment]+ [CH3CH2CH2C=O]+ [CH2CH2CHO]+ [CH2=CH-OH]+ [CH3CO]+ [CH3CH2CH2]+
m/z value of [fragment]+ 41 39 29 29 28 27 15
[molecular fragment]+ [C3H5]+ [C3H3]+ [CH3CH2]+ [HC=O]+ [C2H4]+ [C2H3]+ [CH3]+

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

Equations to explain the most abundant ion peaks of butanal

Formation of m/z 71 ion: [CH3CH2CH2CHO]+  ===>  [CH3CH2CH2C=O]+  +  H

Proton loss from the molecular ion.

Formation of m/z 57 ion: [CH3CH2CH2CHO]+  ===>  [CH2CH2CHO]+  +  CH3

Formation of m/z 44 ion:  [CH3CH2CH2CHO]+  ===>  [CH2=CH-OH]+  +  CH3CH

The m/z 44 ion is the base peak, the most abundant 'stable' ion fragment.

This ion is formed by a rearrangement, followed by a C-C bond fission.

Formation of m/z 28 ion:  [CH3CH2CH2CHO]+  ===>  [CH3CH]+  +  CH2=CH-OH

An alternative to C-C bond fission forming m/z ion 44 above.

Formation of m/z 29 ion: [CH3CH2CH2CHO]+  ===>  [HC=O]+  +  CH3CH2CH2

or alternatively: [CH3CH2CH2CHO]+  ===>  [CH3CH2]+  +  CH2CHO

m/z 54 from water loss: [CH3CH2CH2CHO]+  ===>  [C4H6]+  +  H2O

m/z 28 ion could be [CO]+  or  [CH2=CH2]+  or  [CH3CH]+


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