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Advanced Organic Chemistry: Mass spectrum of cyclohexane

The mass spectrum of cyclohexane

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 cyclohexane

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

Cyclohexane, C6H12 , alkanes structure and naming (c) doc b , alkanes structure and naming (c) doc b , all bond angles ~109o

Interpreting the fragmentation pattern of the mass spectrum of cyclohexane

[M]+ is the molecular ion peak (M) with an m/z of 84 corresponding to [C6H12]+, the original cyclohexane molecule minus an electron.

The small M+1 peak at m/z 85, corresponds to an ionised cyclohexane molecule with one 13C atom in it i.e. an ionised cyclohexane molecule of formula 13C12C5H12

Carbon-13 only accounts for ~1% of all carbon atoms (12C ~99%), but the more carbon atoms in the molecule, the greater the probability of observing this 13C M+1 peak.

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

m/z value of [fragment]+ 69 57 56 55 43 42 41 39 29 27
[molecular fragment]+ [C5H9]+ [C4H9]+ [C4H8]+ [C4H7]+ [C3H7]+ [C3H6]+ [C3H5]+ [C3H3]+ [C2H5]+ [C2H3]+

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

Equations to explain the most abundant ion peaks of cyclohexane

Formation of m/z 56 ion: [C6H12]+  ===>  [C4H8]+  +  CH2=CH2

The m/z 56 ion is the base peak ion, the most abundant and 'stable' ion fragment.

It is formed by the elimination of ethene from the molecular ion.

The m/z values of 83, 69 and 55 are related by the loss of a mass unit of 14 (CH2) from one fragment ion to the next.


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