
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?