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Solution 36

The document analyzes spectroscopic data to determine the structure of an unknown compound. The MS and IR indicate the presence of bromine and either a C≡C or C≡N bond. The NMR data shows signals for a CH3, CH2, and CH group. This suggests a molecular formula of C4H6BrN, which matches the mass spectrometry molecular weight of 147 g/mol. Analysis of the NMR coupling patterns identifies the compound as 3-bromobutyronitrile.

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18 views1 page

Solution 36

The document analyzes spectroscopic data to determine the structure of an unknown compound. The MS and IR indicate the presence of bromine and either a C≡C or C≡N bond. The NMR data shows signals for a CH3, CH2, and CH group. This suggests a molecular formula of C4H6BrN, which matches the mass spectrometry molecular weight of 147 g/mol. Analysis of the NMR coupling patterns identifies the compound as 3-bromobutyronitrile.

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yaboiglyph
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SOLUTION #36

In the MS, the molecular ion occurs at m/z = 147 (odd) and m+2 (149) of approximately equal intensity (i.e. isotope pattern for Br)
This indicates the MW = 147 g / mol.
Odd MW in terms of the notrogen rule implies the presence of an odd number of N atoms.
The IR shows a strong absorption near 2270 cm-1 which is probably C≡C or C≡N. There are no other absorptions of note.... no C=O (near 1700 cm-1) or C=C (near 1600 cm-1) or -OH or -NH (above 3200 cm-1).
The C NMR shows 4 types of C: spC (117 ppm) and then 3 peaks for sp3 hydrocarbon C (0-40 ppm)
H-nmr
d/ppm multiplicity integration assignment
CH coupled to 5H,
4.3 sextet 1H
deshielded
CH2 coupled to 1H, slightly
3.0 doublet 2H
deshielded
1.8 doublet 3H CH3 coupled to 1H

The H NMR shows 3 types of H


H NMR peaks give CH3- , -CH2- and a CH.

Summary....

The MS indicated MW = 147 g/mol and indicated the presence of N and Br.
The IR showed the presence of either C≡C or C≡N, but no C-H peak at about 3300 cm-1
The C NMR shows just 4 C types of which one is sp hybridised.
H NMR gives CH3- , -CH2- and a CH.
Overall then we have CH3- , -CH2-, CH, Br and N.
This gives C4H6BrN= 4 x 12 + 6 x 1 + 79 + 14 = 147 g/mol, so confirming the molecular formula.
Therefore the IHD = 2.

Altogether....

With the pieces we have : CH3- , -CH2-, CH, Br and N.


The H NMR coupling tells us that we have CH3CHCH2-
This leaves Br, C and N and the IHD = 2.
So we need to have C≡N to account for the IHD.
The H-NMR data indicates that the CH is the most desheilded at 4.3ppm which
is most consistent with the Br being attached at that C. 3-bromobutyronitrile
Once we get this far, there is only one it can fit together...

© Dr. Ian Hunt, Department of Chemistry, University of Calgary

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