A couple of weeks ago in my O Chem lab, we had to synthesize Chalcone and then for the second part of it, we had to hydrogenate it and need to determine the product that was produced. We submitted IR and NMR samples for both products and recieved mass spectrums of both as well. There were four potential places on the Chalcone where hydrogenation could have taken place, one at the alkene, one where the ketone is at, one where Cl is at, and one where the methoxy substituent is. From looking at the mass spectrums from both, I believe that the Cl atom was lost and a H atom was replaced in the second reaction. The molecular mass for Chalcone is around 274 and from looking at the mass spectrum for the second product, the molecular peak was around 238, subtracting the mass of Cl. I had a hard time trying to identify the peaks from the NMR spectra and was wondering if somebody could look at what I had so far and how else to determining the remaining peaks. Also for the Chalcone NMR, my prof had said to look for potential peaks in its ketol intermediate but after drawing it out and looking up where peaks are normally found for it, I could only find one corresponding peak for it. The ketol intermediate is what I have drawn out beneath the Chalcone structure in the first NMR spectrum. aOtherwise, I believe I figured out everything for both IR peaks and if somebody could confirm that I have correctly identified the peaks for those spectrums too, I'd appreciate it!
Edit: The top NMR and IR spectrums are those of Chalcone and the bottom NMR and IR spectrums are those of my hydrogenated product.