1. Advanced Pharmaceutical Analysis 13 C NMR Examples
Lecture 7 58
Advanced Pharmaceutical Analysis 13 C NMR Examples
Check 3
Dr. Baraa Ramzi

2. Example 1
A compound with the formula C3H6O2 gives the following proton-decoupled and off-resonance-decoupled spectra. Determine the structure of the compound.

3. Example 1
C3H6O2
IHD=1

4. Example 1
C3H6O2
Looks like carboxylic acid
IHD=1

5. Example 2
Following are proton-decoupled 13C spectra for three isomeric alcohols with the formula C4H10O. An off-resonance analysis yields the multiplicities shown; s = singlet, d = doublet, t = triplet, and q = quartet. Identify the alcohol responsible for each spectrum and assign each peak to an appropriate carbon atom or atoms.

6. Example 2 (A)
C4H10O
IHD=0

7. Example 2 (B)
C4H10O
IHD=0

8. Example 2 (C)
C4H10O
IHD=0

9. Example 3*
The following spectrum is of an ester with formula C5H8O2. Multiplicities are indicated. Draw the structure of the compound and assign each peak.

10. Example 3
C5H8O2
IHD=2

11. Example 4
Following are the 1H and 13C spectra for each of four isomeric bromoalkanes with formula C4H9Br. Assign a structure to each pair of spectra.

14. Example 4 (B)
IHD=0

15. Example 4 (C)
IHD=0

16. Example 4 (D)
IHD=0

17. Example 5
Following are the 1H and 13C spectra for each of three isomeric ketones with formula C7H14O. Assign a structure to each pair of spectra.

18. Example 5 (A)
IHD=1

19. Example 5 (B)
IHD=1

20. Example 5 (C)
IHD=1

21. Example 6
The proton NMR spectrum for a compound with formula C5H12O2 is shown below. The normal carbon-13 NMR spectrum has three peaks. The DEPT-135 and DEPT-90 spectral results are tabulated. Draw the structure of this compound.

22. Example 6
IHD=0

23. Example 7 *
The proton NMR spectrum for a compound with formula C5H10O is shown below. The normal carbon-13 NMR spectrum has three peaks. The DEPT-135 and DEPT-90 spectral results are tabulated. Draw the structure of this compound.

24. Example 7
IHD=1

25. Example 8
The proton NMR spectrum for a compound with formula C5H10O3 is shown below. The normal carbon-13 NMR spectrum has four peaks. The infrared spectrum has a strong band at 1728 cm−1. The DEPT-135 and DEPT-90 spectral results are tabulated. Draw the structure of this compound.

26. Example 8
IHD=1

27. Example 9
The proton NMR spectrum for a compound with formula C9H8O is shown below. The normal carbon-13 NMR spectrum has five peaks. The infrared spectrum has a strong band at 1746 cm -1 . The DEPT-135 and DEPT-90 spectral results are tabulated. Draw the structure of this compound.

28. Example 9
IHD=6

29. Example 10 *
The proton NMR spectrum for a compound with formula C10H12O2 is shown below. The infrared spectrum has a strong band at 1711 cm−1. The normal carbon-13 NMR spectral results are tabulated along with the DEPT-135 and DEPT-90 information. Draw the structure of this compound.
2 pssibilities

30. Example 10
IHD=5

31. Example 11
The proton NMR spectrum of a compound with formula C7H12O3 is shown. The infrared spectrum displays strong bands at 1720 and 1738 cm−1 . The normal carbon-13 and the DEPT experimental results are tabulated. Draw the structure of this compound.

32. Example 11
IHD=2

33. Example 12
The proton NMR spectrum is shown for a compound with formula C5H9NO4. The infrared spectrum displays strong band at 1750 cm−1. The normal carbon-13 and the DEPT experimental results are tabulated. Draw the structure of this compound.

34. Example 12
IHD=2

35. Example 13
The proton NMR spectrum of a compound with formula C6H5NCl2 is shown. The normal carbon-13 and the DEPT experimental results are tabulated. The infrared spectrum shows peaks at 3432 and 3313 cm-1 and a series of medium-sized peaks between 1618 and 1466 cm-1. Draw the structure of this compound.

36. Example 13
IHD=4
Test them + position

37. Example 14
A compound has the chemical formula of C4H8O determine its structure using provided spectra.

38. Example 14
C4H𝟖O
IHD=1

39. Example 14
C4H𝟖O
IHD=1

40. Example 14
C4H𝟖O
IHD=1

41. Example 15
A compound has the chemical formula of C4H6NBr determine its structure using provided spectra.

42. Example 15
C4H6NBr
IHD=2

43. Example 15
C4H6NBr
IHD=2

44. Example 15
C4H6NBr
IHD=2

45. Example 16
A compound has the chemical formula of C5H8O determine its structure using provided spectra.

46. Example 16
C5H𝟖O
IHD=2

47. Example 16
C5H𝟖O
IHD=2

48. Example 16
C5H𝟖O
IHD=2