Identifying Structure based off 1H-NMR & Mass Spectroscopy Data [closed]








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I have almost the whole night trying to identify this structure with no avail as there is always one part that does not fit. The determined formula for this structure was $\ce{C13H17BrO}$ from the $m/z=268$ (M-100%), $m/z=269$ (M+1-14.7%), and $m/z=270$ (M+2-98.6%).


The $\ce{^1H}$-NMR data is as follows with integration in parentheses:


a. $\pu{7.30-7.27 ppm}$: multiplet (5) - arene with 5 hydrogens


b. $\pu{3.20 ppm}$: singlet (2) - R-**CH2**-Br attached to tetra-substituted carbon?


c. $\pu{2.45 ppm}$: triplet (2) - R-CH2-**CH2**-CO-CH3


d. $\pu{2.17 ppm}$: singlet (3) - R-CH2-CO-**CH3**


e. $\pu{1.68 ppm}$: sextet (2) - R-CH2-**CH2**-CH3


f. $\pu{0.90 ppm}$: triplet (3) - R-CH2-**CH3**


And this is the structure I come up with:


[![![enter image description here](https://i.stack.imgur.com/kAXEg.png)](https://i.stack.imgur.com/kAXEg.png)


which is the only structure that fits all the hydrogen integrations, but does not support the chemical shift at all. 


I believe this is part of the molecule


[![enter image description here](https://i.stack.imgur.com/6jbVr.png)](https://i.stack.imgur.com/6jbVr.png)


because it takes care of shifts d,c,e,f. However, it is impossible to attach that structure to the remaining Arene, CH2-Br, and tetra substituted carbon. Actually spent over 6 hours on this problem and I'm losing my mind please help me. 


