Experiment 3 – Mass Spectrometry

In this dry-lab, you must identify the unknown organic compound in your assigned
mass spectrum, as well as identifying the listed fragments in the table.
 All unknowns contain C and H, and may contain either N, O, Cl, or Br.
 Unknowns cannot contain multiple different non-C/H atoms, but might
contain two of the same non-C/H atoms.
o i.e. an unknown cannot contain both O and Br, but could contain two
Br atoms.
 Fragments in your mass spectrum will be the result of breaking bonds in the
parent unknown molecule. Formation of new bonds that were not present
in the original compound is extremely rare.
The following isotopic ratios might be useful for analysing your spectrum:
1
Hydrogen: H (100) : 2H (0.016) 2
H can be completely neglected
12
Carbon: C (100) : 13C (1.11)
14
Nitrogen: N (100) : 15N (0.38) 15
N can be completely neglected
16
Oxygen: O (100) : 17O (0.04) 17
O can be completely neglected
35
Chlorine: Cl (100) : 37Cl (32.5)
79
Bromine: Br (100) : 81Br (98)
Questions to ask as you work through your spectrum:
Do you have peaks at m/Z = 35 and 37 in a ~3:1 ratio?
If so, do you have three heavy peaks in a ~9:6:1 ratio?
Do you have peaks at m/Z = 79 and 81 in a ~1:1 ratio?
If so, do you have three heavy peaks in a ~1:2:1 ratio?
Do you have peaks at m/Z = 14 or 15? What organic fragments could these be?
(hint: they do not contain nitrogen)

1
Mass Spectrum – Unknown #6

2
m Bond ( s ) broken ¿
Rel . Intensity Proposed Fragment
Z form proposed fragment

15 10.3 [12CH3 ]+ Carbon and Carbon single bond

12 Carbon and Carbon single bond + single

28 32.1 CH2N+
nitrogen bonded to hydrogen

13 Carbon and nitrogen single bond + two

29 7.9 CH3N+
hydrogens bonded to carbon

CH3 binding and CH4N binding bond

30 100 [12CH4N]+
broken

2 hydrogens from either of the carbons

42 9.1 [12C2H4N]+
broken off

44 20.2 [12C2H6N]+ Hydrogen from one of the Carbons

45 19.2 [12C2H7N]+ Loss of an electron

Identity of Assigned Unknown: C2H7N , or dimethylamine / ethylamine