1. Problem Day 2 CH343 Bruce A. Hathaway

2. Compound #1: IR sp 2 C-H, sp 3 C-H, C=O, benzene C=C, possible monsubstituted benzene

3. MS Even MW, so assume 0 N’s; no apparent Cl or Br

4. Compound #1: Carbon NMR C=O; 4 benzene C’s; 3 sp 3 C’s

5. Proton NMR

6. Compound #2: IR NH 2 stretches; sp 3 C-H stretches, N-H bend

7. MS Odd MW is probably 1 N; no apparent Cl or Br

8. Compound #2: Carbon NMR Three types of carbons, all sp 3

9. Proton NMR

10. Compound #3: IR OH stretch; sp C-H stretch, sp 3 C-H stretches, CΞC stretch, C-O stretch

11. MS No apparent Cl or Br; even MW is probably no N

12. Compound #3: Carbon NMR CΞC; sp 3 C-O, sp 3 C

13. Proton NMR