Advanced Organic Chemistry: Mass spectrum of butan-1-ol

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Interpreting the mass spectrum of butan-1-ol

(1-butanol, prim-butyl alcohol, n-butyl alcohol) CH3CH2CH2CH2OH

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 butan-1-ol 1-butanol

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Mass spectroscopy - spectra index

mass spectrum of butan-1-ol fragmentation pattern of m/z m/e ions for analysis and identification of 1-butanol image diagram doc brown's advanced organic chemistry revision notes 

Butan-1-ol C4H10O , alcohols and ether structure and naming (c) doc b . alcohols and ether structure and naming (c) doc b

Interpreting fragmentation pattern: mass spectrum of butan-1-ol (1-butanol, n-butyl alcohol)

[M]+ is the molecular ion peak (M) with an m/z of 74 corresponding to [C4H10]+, the original butan-1-ol molecule minus an electron, [CH3CH2CH2CH2OH]+.

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

Identifying the species giving the most prominent peaks (apart from M) in the fragmentation pattern of butan-1-ol.

m/z value of [fragment]+ 57 56 55 45 43 42 41
[molecular fragment]+ [C4H9]+ [C4H8]+ [C4H7]+ [CH2CH2=OH]+ [C3H7]+ [C3H6]+ [C3H5]+
m/z value of [fragment]+ 39 31 29 28 27 19 15
[molecular fragment]+ [C3H3]+ [CH2=OH]+ [CH3CH2]+ [CH2=CH2]+ [C2H3]+ [?]+ [CH3]+

Analysing-explaining the principal ions in the fragmentation pattern of the mass spectrum of butan-1-ol

Suggested equations to explain the most abundant ion peaks of butan-1-ol

Formation of m/z 31 ion: [CH3CH2CH2CH2OH]+  ===>  [CH2=OH]+  +  CH3CH2CH2

Characteristic of the fragmentation of primary alcohols like butan-1-ol and the 2nd most abundant ion.

Formation of m/z 56 ion: [CH3CH2CH2CH2OH]+  ===>  [C4H8]+  +  H2O

The m/z 56 ion is the base peak, the most abundant 'stable' ion fragment, formed by loss of water from the parent molecular ion of butan-1-ol to give an alkene.

Formation of m/z 43 ion: [CH3CH2CH2CH2OH]+  ===>  [CH3CH2CH2]+  +  CH2=OH

Formation of m/z 57 ion: [CH3CH2CH2CH2OH]+  ===>  [CH3CH2CH2CH2]+  +  OH

Formation of m/z 45 ion: [CH3CH2CH2CH2OH]+  ===>  [CH2CH2=OH]+  +  CH3CH2

Formation of m/z 27 ion: [CH2CH2=OH]+  ==> [C2H3]+  +  H2O

Formation of m/z 29 ion: [CH3CH2CH2CH2OH]+  ===>  m/z 29 [CH3CH2]+  +  CH2CH2=OH

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The infrared spectrum of butan-1-ol (1-butanol)

The H-1 NMR spectrum of butan-1-ol (1-butanol)

The C-13 NMR spectrum of butan-1-ol (1-butanol)

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