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Advanced Organic Chemistry: Mass spectrum of ethoxyethane

The mass spectrum of ethoxyethane (diethyl ether)

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 ethoxyethane

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

Ethoxyethane C4H10O, alcohols and ether structure and naming (c) doc b , alcohols and ether structure and naming (c) doc b , alcohols and ether structure and naming (c) doc b

Interpreting the mass spectrum of ethoxyethane (diethyl ether)

[M]+ is the molecular ion peak (M) with an m/z of 74 corresponding to [C4H10O]+, the original ethoxyethane molecule minus an electron, [CH3CH2OCH2CH3]+.

The small M+1 peak at m/z 75, corresponds to an ionised ethoxyethane molecule with one 13C atom in it i.e. an ionised ethoxyethane molecule of formula 13C12C3H10O

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.

Ethoxyethane has 4 carbon atoms, so on average, ~1 in 25 molecules will contain a 13C atom.

In the mass spectrum of ethers, an M+1 ion can also be formed by a hydrogen atom radical combining with the molecular ion i.e. m/z 75 can originate from [M]+  +  H•  ===>  [•MH]+

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

m/z value of [fragment]+ 59 45 43 41 31 29 28 27 15
molecular fragment CH3CH2OCH2 CH3CH2O C2H3O C2HO CH3O CH3CH2 C2H4 C2H3 CH3

Explaining the principal fragments of the mass spectrum of ethoxyethane

The m/z 59 ion is formed by the loss of a methyl group from the parent molecular ion.

[CH3CH2OCH2CH3]+  ===>  [CH3CH2OCH2]+  +  CH3

 The m/z 31 ion is the base peak, the most stable fragment [CH3O]+, structure?

Scission of the C-O bond in the molecular ions gives m/z 45 [CH3CH2O]+  or m/z 29   [CH3CH2]+., both of which have prominent intensities.


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