Mass spectrometry worksheet

1. For each of the following compounds complete the table to identify the ion responsible
for each mass.
Spectra courtesy of NIST Chemistry WebBook: https://webbook.nist.gov/chemistry/
Note: you must give structural formulae for all particles

a. Propan-1-ol (CH3CH2CH2OH)

Give the displayed formula of propan-1-ol

mass spectrum

31

29
59
43 60

Mass of peak Mass lost Atom/group lost Identity of fragment

60

59

43

31

29

© Quality Resources 1
b. Propanal (CH3CH2CHO)

Displayed formula
H H O
H C C C
H H H

mass spectrum

58
29

57

M+1 peak

Mass of peak Mass lost Atom/group lost Identity of fragment

58

57

29

© Quality Resources 2
c. Methyl benzoate (C6H5COOCH3)

Structural formula
O
C
O CH3

mass spectrum

105

77

136

Mass of peak Mass lost Atom/group lost Identity of fragment

136

105

77

© Quality Resources 3
d. Ethyl ethanoate (CH3COOCH2CH3)

Structural formula
H O H H
H C C O C C H
H H H
mass spectrum

43

29
15 73 88

Mass of peak Mass lost Atom/group lost Identity of fragment

88

73

43

29

15

© Quality Resources 4
2. For each of the following use the mass spectrum to identify the compound. Two
possible structures are given in each case.
Give reasons for your answer.
Then complete the table using structural formulae.

a. Compound X has one of the following structures

O H H H O H
or methyl ethanoate
H C O C C H H C C O C H
ethyl methanoate H H H H

43
Mass spectrum of compound X

74

59
15

Mass of peak Mass lost Atom/group lost Identity of fragment

74

59

43

15

© Quality Resources 5
b. Compound Y has one of the following structures

H H H H H H H H m/z - 57 and m/z = 29

or
H C C C C C H H C C C C C H
H O H H H H H O H H
pentanone

43
Mass spectrum of compound Y

86

71

Mass of peak Mass lost Atom/group lost Identity of fragment

86

71

43

© Quality Resources 6
3. Use the information given to identify the following compound.
Show all your working and reasoning.
Then complete the table using structural formulae.

% composition by mass
C=48.6%. H = 8.1%, O = 43.2%

Infrared absorptions
Very broad absorption at 2500-3300 cm-1 due to O-H of carboxylic acid
Sharp absorption at 1630-1820 cm-1 due to C=O

74
45
29

73

57

Mass of peak Mass lost Atom/group lost Identity of fragment

74

73

57

45

29

© Quality Resources 7