General Note: If a printer is not accessible, the problem set may be completed on regular paper, but please ensure all answers are clear. Notations for IR and NMR may be written out and listed by wavenumbers and ppm, respectively. if this is the case or provided space is insufficient 1. (3 points) For the structure and ‘H NMR spectrum shown below, match the labeled hydrogen atoms on the molecule (A-D) with the corresponding signals in the spectrum using the boxes provided. Integration and splitting are noted. 3H, S 1H, m PPM Instructions for Problems 2-4: Provide the structure of the compound that corresponds to the set of spectra. Your notations and analysis must be shown for full credit. This includes diagnostic peaks in the IR, if any MS fragmentations are notable, and degrees of unsaturation (DU’s). In regards to NMR: signals integration (for HNMR), chemical shift, and splitting (for HNMR) are relevant for the analysis and elucidation of fragments to guide toward full structure elucidation.

2. (4 points) Formula: C.H.O 100 Mass Spectrum 13C NMR Spectrum (50.0 M . CDC, s on 1160 08 (ppm) “H NMR Spectrum (200 MHz CDC, otion TA Гр 3H,t 10 9 8 7 6 5 4 3 2 1

3. (4 points) Formula: C.H.Oz 13C NMR Spectrum 1000 CBI, LA C D 200 160 80 40 0 5 (ppm) H NMR Spectrum 200 CDC, 10 9 8 7 6 5 4 3 2 1 8 (ppm)

4. (4 points) Formula: C.H.Br 100F Mes Spectrum 0 120 100 200 NMR Spectrum 200 08 (ppm) ‘H NUR Spectrum 200 M CDO, expansions 1H m 109 – 2 8 (ppm)