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Advanced Organic Chemistry: Mass spectrum of propanamide

The mass spectrum of propanamide (propionamide)

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 propanamide

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

propanamide (propionamide), C3H7NO, (c) doc b, (c) doc b, (c) doc b

Interpreting the fragmentation pattern of the mass spectrum of propanamide

[M]+ is the molecular ion peak (M) with an m/z of 73 corresponding to [C3H7NO]+, the original propanamide molecule minus an electron, [CH3CH2CONH2]+.

The small M+1 peak at m/z 74, corresponds to an ionised propanamide molecule with one 13C atom in it i.e. an ionised propanamide molecule of formula 13C12C2H7NO

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

m/z value of [fragment]+ 72 57 55 44 29 15
[molecular fragment]+ [C3H6NO]+ [CH3CH2C=O]+ [C3H3O]+ [O=C-NH2]+ [CH3CH2]+ [CH3]+

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

Equations to explain the most abundant ion peaks of propanamide

Formation of m/z 57 ion: [CH3CH2CONH2]+  ===>  [CH3CH2C=O]+  +  NH2

Formation of m/z 44 ion: [CH3CH2CONH2]+  ===>  [O=C-NH2]+  +  CH3CH2

The m/z 44 ion is the base peak, the most abundant 'stable' ion fragment.

Formation of m/z 29 ion: [CH3CH2CONH2]+  ===>  [CH3CH2]+  +  CONH2

Formation of m/z 15 ion: [three of above]+  ===>  [CH3]+  +  residue


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