2. The Study Cycle – It Works !
P preview, preread – look at figures, bold A attend and ask R review soon S study serially – repetition is the key P problems, problems, problems & pencils A focus on approach needed in problem R reflect, assess, self test

3. Chemistry 250-02 Organic Chemistry I Fall, 2014 Day 25 11/3/14
Organic Chemistry I
Fall, 2014
Day 25 11/3/14
Structure Determination and Spectroscopy
Chapter 13 (NMR) & ChemAct L-03,L-04

4. NMR

5. Reaction Types

6. Substitution vs. Elimination
How can we identify and distinguish
between these two compounds?

7. Nuclear Magnetic Resonance
odd atomic number (# p) or
odd atomic mass (# p + # n)

8. The NMR Spectrometer

9. The Drew NMR Spectrometer !

10. NMR Active Nuclei

11. 1H
TMS TT
13C
TMS

12. 13C NMR and 1H NMR 1H
13C

13. 13C NMR and 1H NMR
13C 1H

14. 13C NMR

15. 13C NMR 3 1 4 2

17. Sponsor: Tri-Beta Co-sponsors: DUBS, DUCS, GSE, MIND, DHO
Science Internship Panel Are you looking for an internship but don’t know where to get started? Come hear about internships completed by your peers! Speakers covering topics in: biology, neuroscience, chemistry, physics, ESS, medicine and veterinary
Sponsor: Tri-Beta
Co-sponsors: DUBS, DUCS, GSE, MIND, DHO
Time: 5:30 pm
Date: November 6th
Location: Crawford Hall

18. Chem Act L-03 13C NMR Models 1 - 2

19. Chem Act L-03 QCT 11

20. The painkiller Demerol has the structure shown below
The painkiller Demerol has the structure shown below. How many peaks would you expect to see in the 13C NMR spectrum of this substance? 10 11 12 14 15

21. Which of the following molecules best fits the following 13C NMR data
Which of the following molecules best fits the following 13C NMR data? 13C NMR data: 20, 22, 32, 44, 67 ppm 1. 2. 4. 3.

22. Chem Act L-03 Models 3 - 6

23. 13C NMR 1H undecoupled = coupled or 1H decoupled
coupled
decoupled

24. 13C NMR 2-bromobutane
decoupled
undecoupled

25. Chem Act L-03 Exercise 3 page 293

26. 13C NMR How many different carbons ?

27. How many signals will appear in the decoupled 13C NMR spectrum of the following molecule?2 3 4 5

28. Problem 13.51 Assign the Peaks

29. Problem 13.51 Assign the Peaks
meta
ortho
CH2
CH3
para
C=O
ipso

30. 13C NMR Are the peak heights (areas) identical ?

31. What is the pattern of signals in the undecoupled 13C NMR spectrum of the following molecule?
s s d t q
s d d t q
d d s d q
s s s t q
d d d d q

32. How many signals will appear in the 13C NMR spectrum of the following molecule?4 5 6 7

33. Advanced 13C NMR DEPT 90 for CH only CH3 positive DEPT 135
DEPT 90 for CH only
CH3 positive
DEPT 135
CH2 negative

34. Uses of 13C NMR E2
How many different carbons ?

35. Problem 13.59

38. Sponsor: Tri-Beta Co-sponsors: DUBS, DUCS, GSE, MIND, DHO
Science Internship Panel Are you looking for an internship but don’t know where to get started? Come hear about internships completed by your peers! Speakers covering topics in: biology, neuroscience, chemistry, physics, ESS, medicine and veterinary
Sponsor: Tri-Beta
Co-sponsors: DUBS, DUCS, GSE, MIND, DHO
Time: 5:30 pm
Date: November 6th
Location: Crawford Hall

39. Spectroscopy Problems

40. 13C NMR Problems – C5H11Cl

41. 1H NMR Chem Act L4

42. The Chemical Shift

43. 1H NMR Look Complicated – Why ?1H
13C undecoupled
13C decoupled

44. Spin-Spin Coupling (JHz)

45. # Peaks = N + 1

46. ChemAct 1S-6

47. Spin-Spin Splitting (Multiplicity)

48. Homotopic, Enantiotopic, Diastereotopic

49. What Kinds of H’s Are These ? Problems 13.13, 13.40, 13.40

50. Problem C3H6Br2

51. Problem C4H7O2Cl IR 1740 cm-1

52. Problem 13.45a C4H9Br

53. Problem 13.45b C4H8Cl2

54. Problem C8H9Br

55. Problem 13.58a C5H10O

56. Problem 13.58b C7H7Br

57. Problem 13.58c C8H9Br

58. Uses of NMR

59. How Can You Distinguish?

60. Problems 13.43 and 13.49 How Can You Distinguish by NMR ?

61. Problem 13.50 How Can You Distinguish by IR, NMR and UV ?

62. C60