Very confused on combo structure problem (given IR,HNMR,MS)

Mar 2015
1
0
Hello All,

I am in serious trouble here with this structural determination. I am given IR, HNMR, and MS (with a CI (methane) MS). Here's where I am at:

I know it must be a Carbox' Acid judging by the IR and characteristic Base Peak at 60 amu and 1 H at ~11ppm. The thing is I can't come up with a molecular formula to even take a shot at the HNMR integrations. There must be a bromine as the M and M+2 peaks are essentially the same height. But the M is odd, so there must be a Nitrogen somewhere. The fact that there are so many heteroatoms is throwing me off immensely(CxHxBrNO2 ?). I can't find any indicative peaks for Nitrogen containing compounds on any of the spectra. I am at my wits end with this. I normally can solve these relatively well but I am stuck. There are no sp2 peaks on IR but Every formula I come up with has either a Negative Double bond equivalence or something ridiculous like 5 and it can't be aromatic. Are there any other ways to get an odd Molecular Ion peak?? Please help me! :( It would be much appreciated. I have attached the spectra if you could just vaguely point me in the right direction.
 

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