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Spectroscopy Manual

Spectroscopy Manual

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Published by anthor
Chemistry, IB
Chemistry, IB

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Published by: anthor on Jan 29, 2012
Copyright:Attribution Non-commercial

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03/04/2013

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DETERMINATION OF THE STRUCTUREFROM SPECTRAL DATAIB Chemistry
1
 
Example 1
C
7
H
16
O
MW 116First calculate the degree of unsaturation: the result is 0. The compound will
not
have aring or a double bond.
IR Spectrum
The compound has an oxygen, but no double bonds, so it must either be an alcohol (-OH)or an ether (-O-). Alcohols are quite distinctive in IR, showing up with a strong, broad bandin the region 3500-3250. Note the broad band at 3391: this indicates that the compoundsis indeed an alcohol. You can also look for the C-OH stretch at 1260-1050.
Think of possible structures
Now we know that the compound has an -OH group, but there are lot of ways that thisseven-carbon molecule could be put together. It could be straight-chained or it could bebranched; the -OH group could be (theoretically) anywhere in the molecule. Let's look atthe NMR to get an idea of how many different hydrogens are in the molecule so that wecan narrow down the number of possible structures.
2
 
Proton NMR Spectrum
The NMR of this compound is below:There are only four different kinds of protons, and 12 of them (at 0.9 ppm) are next to acarbon that has only one hydrogen (because it is a doublet). This indicates that themolecule has
two
of the sub-structures below:These two sub-structures account for 6 of the 7 carbons in the molecule. Therefore the"something" in each must be the same carbon. Let's put them end-to-end and replace the"something" with a carbon, then sketch in the proper number of bonds:Now we need to place an -OH group in the molecule. It can't be on either of the carbonsthat are connected to the two methyl groups, because the position of each hydrogen inblue is dictated by the fact that it splits the 12 hydrogens at 0.9 ppm into a doublet.Therefore, it must be on the middle carbon, like this:In the NMR, protons on the same carbon as an -OH group - the hydrogen in
purple
above- will show up from 2-4 ppm. Sure enough, there is a peak constituting one proton at 3.1ppm; furthermore, this peak is a triplet indicating 2 protons (blue) on adjacent carbons.
3

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