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Mass Spectroscopy Part 2 Lecture4 Solved Problems

This document discusses mass spectroscopy problems and their solutions: 1) A compound with molecular formula C4H8O and peaks at m/z 44 and 29 is identified as butanal. The m/z 44 peak arises from a McLafferty rearrangement of the carbonyl group. 2) In the mass spectrum of 2,6-dimethyl-4-heptanol, prominent peaks at m/z 87, 111, and 126 could represent reasonable fragment structures. 3) Butyl isopropyl ether matches Fig 1 due to ions at m/z 101 and 73, while butyl propyl ether matches Fig 2 lacking an m/z 101 ion. 4) 3-

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251 views8 pages

Mass Spectroscopy Part 2 Lecture4 Solved Problems

This document discusses mass spectroscopy problems and their solutions: 1) A compound with molecular formula C4H8O and peaks at m/z 44 and 29 is identified as butanal. The m/z 44 peak arises from a McLafferty rearrangement of the carbonyl group. 2) In the mass spectrum of 2,6-dimethyl-4-heptanol, prominent peaks at m/z 87, 111, and 126 could represent reasonable fragment structures. 3) Butyl isopropyl ether matches Fig 1 due to ions at m/z 101 and 73, while butyl propyl ether matches Fig 2 lacking an m/z 101 ion. 4) 3-

Uploaded by

Mvita Henoc
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Mass Spectroscopy: PART 2

some solved problems


Question 1
• A compound with molecular formula C4H8O has a strong IR adsorption at 1730 cm-1. Its mass spectrum includes key peaks at
m/z 44 (the base peak) and m/z 29. Propose a structure and write fragmentation equations showing how these peaks are
formed.

Answer: the compound is butanal. The peak at m/z 44 arises from a MacLafferty rearrangement (see next slide for an
example). This rearrangement happens to carbonyl compounds that have a hydrogen on their alpha carbon.
 Ketones
● McLafferty rearrangement

H
O OH OH
+

1st McL. Rearr. H


O OH

(m/e = 86)
nd
2 McL. Rearr.

OH
+
(m/e = 58)
Ch. 9 - 3
Question 2

• In a mass spectrum of 2,6-dimethyl-4-heptanol there are prominent


peaks at m/z 87,111 and 126. Propose reasonable structures for these
fragment ions.

• Answer:
Question 3

• Match the following MS spectra i.e. Fig 1 and 2 to the corresponding compounds shown below(see your
notes on how ethers fragment).

Butyl propyl ether

Butyl isopropyl ether

Fig 1

Fig 2
Answer:
Fragmentation for butyl isopropyl ether has both peaks at m/z 101 and m/z 73 thus will match with Fig 1

Fragmentation for butyl propyl ether : this doesn’t have an ion at m/z 101 thus will match with Fig 2
Question 4
• 3-methylpentane has a peak of very low relative intensity at M+ -15. It has a peak of very high relative
abundance at M+ -29. Explain this observation

• Answer:
• If you have further questions regarding these examples please feel
free to consult for further clarification

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