NMR Question

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Fire Fly
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NMR Question

Post by Fire Fly »

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I'm doing an NMR analysis of the compound propyl p-tolyl ether that I had to synthesize in lab using p-Cresol and 1-bromo-propane but my data is a bit perplexing. All of the peaks are in the right place and match the approximate literature positions. But, the integration values suggest a completely different compound.

Molecular formula: C10H14O
Total integration value: 200
Index of hydrogen deficiency: 4

~1.0 ppm: 3 peaks (should be 3 H's but integration indicates 2H)
integration value: 28.86

~1.8 ppm: 6 peaks (should be 2 H's but integration indicates 1H)
intgration value: 19.01

~2.3 ppm: 1 peak ( should be 3 H's but data suggests 2H)
integration value: 28.65

~3.9 ppm: 3 peaks (should be 2 H's but data suggests 1H)
integration value: 19.21

~6.8 ppm: 2 peaks (should be 2 but says 4)
integration value: 50.20

~7.0 ppm: 2 peaks (should be 2 but says 4)
integration value: 49.80

There are other peaks but are most likey due to residual water or some other reason:
~1.35 ppm: integration value of 2.47
~1.55 ppm: integration value of 1.8

Does anyone have any idea what is going on?
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Fire Fly
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Location: Grand old Badger State

Post by Fire Fly »

Ok, that's weird. I just noticed that the scaled down integration values, described above, seem to suggest something else but the zoomed out NMR has integration values that match the literature values. Zoomed out version's integration values:

~1.0 ppm: 21.29 -> 3H
~1.8 ppm: 14.02 -> 2H
~2.3 ppm: 21.14 -> 3H
~3.9 ppm: 14.17 -> 2H
~6.8 ppm: 13.17 -> 2H
~7.1 ppm: 13.06 -> 2H

The total integration value is 100. Divide that by 14 H's and it comes out to ~7. Divide each of the integration values by 7 and it comes out to what is described above. Weird.
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