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Advanced Organic Chemistry: Mass spectrum of cyclopentane

The mass spectrum of cyclopentane

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 cyclopentane

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

Cyclopentane, C5H10 , alkanes structure and naming (c) doc b, alkanes structure and naming (c) doc b, all bond angles ~109o, but it is NOT planar, pentagon is slightly bent.

Interpreting the fragmentation pattern of the mass spectrum of cyclopentane

[M]+ is the molecular ion peak (M) with an m/z of 70 corresponding to [C5H10]+, the original cyclopentane molecule minus an electron, [alkanes structure and naming (c) doc b]+.

The small M+1 peak at m/z 71, corresponds to an ionised cyclopentane molecule with one 13C atom in it i.e. an ionised cyclopentane molecule of formula 13C12C4H10

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

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

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

Equations to explain the most abundant ion peaks of cyclopentane

Formation of m/z 42 ion: [alkanes structure and naming (c) doc b]+  ===>  [C3H6]+  +  C2H4

The m/z 42 ion is the base peak ion, the most abundant and 'stable' ion fragment.

This equates to a loss of two CH2 units from a broken cyclopentane ring.

Formation of m/z 71 ion by proton loss: [alkanes structure and naming (c) doc b]+  ===>  [C5H9]+  +   H

and then does this rapidly break down losing a CH2 group to give the prominent m/z 55 ion?

 [C5H9]+  ===>  [C4H7]+  +  CH2


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