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CHEM 380 Problem Set 3

The document outlines a problem set for a chemistry course, focusing on calculations related to molecular weights and mass spectrometry of various compounds. It includes tasks such as estimating M+1 and M+2 peak percentages, analyzing mass spectra of insect pheromones, and identifying functional groups and volatility of compounds. Additionally, it involves comparing spectra of 1-bromohexane and 1-chlorohexane to distinguish between them based on molecular ions and isotopic signatures.

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Jiayu Shi
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27 views6 pages

CHEM 380 Problem Set 3

The document outlines a problem set for a chemistry course, focusing on calculations related to molecular weights and mass spectrometry of various compounds. It includes tasks such as estimating M+1 and M+2 peak percentages, analyzing mass spectra of insect pheromones, and identifying functional groups and volatility of compounds. Additionally, it involves comparing spectra of 1-bromohexane and 1-chlorohexane to distinguish between them based on molecular ions and isotopic signatures.

Uploaded by

Jiayu Shi
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd

CHEM 380 Problem Set 3 EP

1. In your text, in Table 3.3, they show several formulae with the same low-resolution molecular
weight of 60.1. So, the molecular ion, M+•, is 60 amu, the M+1 ion is 61 amu and the M+2 is 62
amu at low m/z resolution. Complete the calculations we start in lecture for these formulas, to
estimate what percentage the M+1 and the M+2 peaks will be relative to M+•.

a) C2H4O2 b) CH4N2O

2. The following three compounds are present in the pheromone of an insect:


A C19H36O2, MS: m/z (intensity relative to most intense peak): 298(1.5%), 297 (2.4%) M+•
296(10.7%), 265(19.2%), 264(42.0%), 237(3.1%), 223(4.1%), 209(1.7%), 195(1.7%),
181(3.8%), 167(3.8%), 153(5.6%), 139(8.3%), 113(3.6%), 99(5.4%), 91(2.7%), 85(10%),
74(100%), 71(11.7%), 57(28%), 55(80%), 43(43%), 29(16%), 15(2.9%).
B C20H38O2, the RI in the GC trace of this compound is exactly 100 higher than that of
compound A, MS: m/z (intensity): 312(3.0%), 311(9.9%), M+• 310 (20.9%), 265(31.8%),
264(62.6%), 237(3%), 223(6.3%), 209(1.6%), 195(2.0%), 181(5.4%), 167(4.5%), 153(6.8%),
139(9.4%), 113(3.5%), 99(7.3%), 91(3.2%), 88(89.6%), 85(12%), 71(18%), 57(34.7%),
55(100%), 43(54.2%), 41(63.3%), 29(35%).
C C19H34O2, the RI of this compound in the GC trace is 15 units less than that of compound A.
MS: m/z (intensity): 295(2.7%), M+• 294(12.3%), 264(2.3%), 179(1.7%), 165(2.9%),
151(5.3%), 137(7.5%), 123(13%), 97(12.7%), 91(7.5%), 83(19.6%), 81(87%), 74(12.3%),
69(34.3%), 67(100), 57(7.2%), 55(60.3%), 43(17.9%), 41(55.5%), 29(30%), 15(7%).
a) Fill in the following table, using the data provided for these compounds
Compound Index of H- Diagnostic IR m/z of the base Volatility *
deficiency peak(s) peak in the MS
A

* Indicate which is most, medium and least volatile.


b) Which two compounds are homologs of each other? How can you tell (there are at least two
ways).

c) Based on the IR and on diagnostic MS peaks, what is the polar functional group in all these
compounds? Show your reasoning.

d) Do these compounds have any other functional group, apart from the polar one? If yes, which
one?

e) Do these compounds have alkyl chains as part of their structures? How can you tell in the IR?
How can you tell in the MS?

f) Verify the m/z of the molecular ions of A-C.


g) Verify the M+1 intensities relative to the molecular ion, given for the mass spectra. Note:
remember to normalize those intensities such that, for this calculation, the intensity of M+• is
taken as 100%.

h) Based on the spectra and all the information gathered from them above, try to draw a structure
for compounds A-C.

3. Given below are mass spectra of 1-bromohexane and 1-chlorohexane.

A)
B)

a) Which spectrum corresponds to which compound?


Ask yourself: i) can I see a molecular ion (i.e. what is the molecular weight of these
compounds)? Note: the molecular ion does not always show. ii) Are there any isotopic signatures
that help me distinguish the two halogens?
b) Try to assign some of the fragment ions you see there, particularly those that help you
distinguish the bromide from the chloride.

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