1. Fig. 13.1 NMRIRUV

2. Fig. 13.2 NMR: excited spin state IR: excited vibrational state UV: excited electronic state

3. Fig. 13.30

4. Tab. 13.4

5. Fig. 13.31 “fingerprint region”

6. Fig. 13.32

7. Fig. 13.33

8. Fig. 13.34

9. Fig. 13.35

10. Which one of the following compounds is most consistent with the IR given?

11. IR: Isolation of Cinnamon Oil from Cinnamon Exp. [11C] Mayo, pp. 213 – 218. Please note the prior reading assignments given on p. 213. Your write-up should include the following: Data from the experiment including mass of oil, percent recovery from cinnamon, IR spectrum. Structure of cinnamon oil, with an analysis of the IR spectrum. Problems 6-77, 6-78, 6-79, 6-80 Steam Distillation – http:wiley.com/college/chem/mayo321850/wave_s.html (under Reference Discussions pp. 27-30)

12. Fig. 13.1 NMRIRUV

13. Fig. 13.2 NMR: excited spin state IR: excited vibrational state UV: excited electronic state

14. Fig. 13.3 The lower energy orientation is the one parallel to H o and more nuclei have this orientation.

15. Fig. 13.4 The energy difference in the two spin states is proportional to the strength of the applied field. 4.7 Tesla - 200MHz (radiofrequency)

16. Fig. 13.5 Source of energy to excite nucleus Aligns nuclear spins Contains sample, may have deuterated solvent Detects the absorption of rf radiation

17. Fig. 13.23a Number of signals – number of nonequivalent protons (H) Chemical shift – electronic environment of the proton, represented by ppm Integration – number of equivalent protons (H), represented as area beneath the curve Multiplicity – number of protons (H) on the adjacent positions

18. Fig. 13.6 Alone, a proton would feel the full strength of the external field, but a proton in an organic molecule responds to both the external field plus any local fields within the molecule. Electrons “shield” the proton from the full effects of the magnetic field. Chemical Shift

19. Fig. 13.7 Electron density “shields” the proton from the full effects of the external magnetic field. H-C-CH-C-XH-C=CH-ArH-C=O Chemical Shift

20. Tab. 13.1 H-C-X 2-5 ppm Chemical Shift

21. Fig. 13.11 Integration

22. C8H8O2C8H8O2 http://www.chem.ucla/~webspectra

23. Fig. 13.12 Multiplicity n+1 Rule - A signal is split into n+1 peaks, where n=number of adjacent protons (H)

24. Fig. 13.15 C 2 H 5 Br 2 3 Deduce structure of :

25. Fig. 13.17 1 H 6 H Deduce structure of C 3 H 7 Cl

26. C8H8O2C8H8O2 GO TO web site

27. Fig. 13.19

28. Fig. 13.20

29. Fig. 13.21 -OH protons are exchangeable

30. Fig. 13.22

31. Tab. 13.3

32. Fig. 13.23b

33. Fig. 13.24

34. Fig. 13.25

35. Fig. 13.26a

36. Fig. 13.26b

37. Fig. 13.28

38. Fig. 13.29

39. Fig. 13.37

40. Tab. 13.5

41. Fig. 13.38

42. Fig. 13.39

43. Fig. 13.40 M+ base peak

44. Fig. 13.41 chlorobenzene

45. Fig. 13.42 decane base peak M+ molecular ion peak

46. Fig. 13.43 propylbenzene

47. Fig. 13.44 GC-MS

48. Spectra for homework problems at the end of Chapter 13 -

49. Fig. 13.45

50. Fig. 13.46a

51. Fig. 13.46b

52. Fig. 13.47a

53. Fig. 13.47b

54. Fig. 13.48a

55. Fig. 13.48b

56. Fig. 13.49a

57. Fig. 13.49b

58. Fig. 13.49c

59. Fig. 13.49d