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

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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, , ,

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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