Name: ______________________

Class: _________________

Date: _________

ID: A

Assignment #2
Multiple Choice Identify the choice that best completes the statement or answers the question. ____ 1. Which of the following compounds corresponds to the IR spectrum shown here?

a.

d.

b.

e.

c.

Name: ______________________ ____ 2. Which of the following compounds corresponds to the IR spectrum shown here?

ID: A

a.

d.

b.

e.

c.

Name: ______________________ ____ 3. What type of compound corresponds to the IR spectrum shown here?

ID: A

a. b. c. ____

ketone carboxylic acid amine

d. e.

alcohol alkane

4. Chemical shift is a. the area under a given signal b. the total number of neighbors that a given hydrogen has c. the location of a signal along the x-axis, reported in ppm d. the number of peaks into which a signal is split e. the distance between the individual lines in a signal, reported in Hz 5. What do you expect to be the integration value of the signal generated by HA protons in the 1 H NMR spectrum for this molecule?

____

a. b. c.

0 1 2

d. e.

3 4

Name: ______________________ ____ 6. Which structure matches the 1 H NMR spectrum shown here?

ID: A

a.

d.

b.

e.

c.

Name: ______________________ ____

ID: A

7. Which hydrogen would have a signal farthest upfield in the 1 H NMR spectrum for this molecule?

a. b. c. ____

A B C

d. e.

D E

8. Which of the following compounds corresponds to the 1 H NMR spectrum shown here?

a.

d.

b.

e.

c.

Name: ______________________ ____ 9. How many lines do you expect in the signal for HA?

ID: A

a. b. c. d. e.

2 3 6 7 There is insufficient information to answer the question.

Name: ______________________ ____ 10. To which structure does this 1 H NMR spectrum correspond?

ID: A

a.

d.

b.

e.

c.

Name: ______________________ ____ 11. To which structure does this 1 H NMR spectrum correspond?

ID: A

a.

d.

b.

e.

c.

Name: ______________________ ____ 12. To which structure does this 1 H NMR spectrum correspond?

ID: A

a.

d.

b.

e.

c.

Name: ______________________ ____ 13. Which of the following compounds corresponds to the spectrum shown here?

ID: A

a.

d.

b.

e.

c.

10

Name: ______________________ ____ 14. Which of the following is the major product of the reaction conditions shown?

ID: A

a.

d.

b.

e.

c.

11

Name: ______________________ ____ 15. Which of the following is the major product of the reaction conditions shown?

ID: A

a.

d.

b.

e.

c.

12

Name: ______________________ ____ 16. Which is a mechanistic intermediate in the following transformation?

ID: A

a.

d.

b.

e.

c.

____ 17. Which reagents would you use to accomplish the following transformation?

a. b. c.

LiAlH4 , then H3 O+ NaBH4 in methanol 1. CH3 MgBr 2. H3 O+

d. e.

H2 , Pd/C CH3 MgBr and H3 O+

13

Name: ______________________

ID: A

____ 18. Which of the following compounds will not react with CrO3 /pyridine to give a carbonyl compound?

a.

d.

b.

e.

c.

____ 19. What is the final product of this reaction?

a.

d.

b.

e.

c.

14

Name: ______________________ ____ 20. Which reagent would you use to effect this transformation?

ID: A

a. b. c.

HIO4 H2 SO4 O3

d. e.

KMnO4 NaBH4

____ 21. Which of the following compounds corresponds to the spectrum shown here?

a.

d.

b.

e.

c.

15

Name: ______________________ ____ 22. Which of these carboxylic acids is most acidic?

ID: A

a.

d.

b.

e.

c.

16

Name: ______________________ ____ 23. Predict the product of the following reaction.

ID: A

a.

d.

b.

e.

c.

____ 24. Which of the following reagents could be used to accomplish the following transformation?

a. b. c.

O3 , then H2 O2 KMnO4 and H2 O O3 , then (CH3 ) 2 S

d. e.

NaOH, H2 O, then H3 O+ Either a or b

17

Name: ______________________ ____ 25. Predict the major organic product of the following reaction.

ID: A

a.

b.

c.

d.

e.

18

Name: ______________________ ____ 26. What is the major organic product of the following reaction?

ID: A

a.

d.

b.

e.

c.

19

Name: ______________________ ____ 27. What is the product of the following reaction?

ID: A

a.

b.

c.

d.

e.

No reaction would occur.

20

Name: ______________________ ____ 28. What is the product of the following reaction conditions?

ID: A

a.

b.

c.

d.

e.

21

Name: ______________________ ____ 29. Which of the following structures will not decarboxylate when heated?

ID: A

a. b. c.

I II and III II, III, and IV

d. e.

II, III, and V I and IV

22

Name: ______________________ ____ 30. What is the product of the reaction shown here?

ID: A

a.

b.

c.

d.

e.

23

Name: ______________________ ____ 31. Which of these structures is not a mechanistic intermediate in acid-catalyzed esterification of a carboxylic acid?

ID: A

a.

d.

b.

e.

c.

24

Name: ______________________

ID: A

____ 32. Which of the following compounds is the major organic product of the reaction conditions shown?

a.

d.

b.

e.

c.

____ 33. Which of the following reagents would you use to accomplish this transformation?

a. b. c.

NaBH4 LiAlH4 DIBAL-H

d. e.

H2 H3 O+

25

Name: ______________________ ____ 34. What is the final product of the reaction conditions shown?

ID: A

a.

d.

b.

e.

c.

26

Name: ______________________ ____ 35. What is the product of the following sequence of reactions?

ID: A

a.

d.

b.

e.

c.

____ 36. What conditions could be used to accomplish the following transformation?

a. b. c.

H2 /Pd or Raney Ni/H2 LiAlH4 , then H2 O Br2 , then H2 O and heat

d. e.

NaBH4 in methanol solvent Both b and c

27

Name: ______________________ ____ 37. Predict the major organic product of the following reaction.

ID: A

a.

d.

b.

e.

c.

28

Name: ______________________ ____ 38. Which of the following is the correct product of the reaction conditions shown?

ID: A

a.

d.

b.

e.

c.

29

Name: ______________________ ____ 39. Which of the following is the correct product of the reaction sequence shown?

ID: A

a.

d.

b.

e.

c.

30

Name: ______________________ ____ 40. Which of the following is the correct product of the conditions shown?

ID: A

a.

d.

b.

e.

c.

31

Name: ______________________ ____ 41. What is the product of the reaction conditions shown?

ID: A

a.

d.

b.

e.

c.

32

Name: ______________________ ____ 42. What is the final product of the following reaction sequence?

ID: A

a.

b.

c.

d.

e.

33

Name: ______________________ ____ 43. What is the final product of this reaction sequence?

ID: A

a.

d.

b.

e.

c.

34

Name: ______________________

ID: A

____ 44. What are the starting materials needed to make the molecule shown using an aldol condensation?

a.

b.

c.

d.

e.

35

Name: ______________________ ____ 45. What is the product of this reaction?

ID: A

a.

d.

b.

e.

c.

36

Name: ______________________ ____ 46. What is the product of the following reaction conditions?

ID: A

a.

d.

b.

e.

None of these is the product of the conditions shown.

c.

37

Name: ______________________ ____ 47. Which of these compounds could reasonably form under the reaction conditions?

ID: A

a.

d.

b.

e.

Either c or d can form.

c.

38

Name: ______________________ ____ 48. What is the product of this reaction?

ID: A

a.

d.

b.

e.

c.

39

Name: ______________________ ____ 49. What is the product of this reaction?

ID: A

a.

d.

b.

e.

c.

40

Name: ______________________ ____ 50. What is the product of the reaction conditions shown?

ID: A

a.

d.

b.

e.

c.

41

Name: ______________________ Short Answer 51. Match the three compounds shown here to the three IR spectra.

ID: A

42

Name: ______________________

ID: A

52. Are the two hydrogens indicated homotopic, enantiotopic, or diastereotopic?

43

Name: ______________________ 53. Predict the splitting pattern of the indicated hydrogen in the following structure.

ID: A

54. The IR, 1 H NMR, and mass spectra for a compound with molecular formula C7 H1 4O are shown. The molecular ion is at m/z 114, and the base peak is at m/z 57. Determine the structure of the compound.

44

Name: ______________________

ID: A

55. Match each of these 1 H NMR spectra to the correct compound. Then assign each signal in both spectra to the corresponding hydrogen(s).

45

Name: ______________________

ID: A

56. A compound with 4 degrees of unsaturation has the molecular formula C1 0H1 4O. Its IR and 1 H NMR spectra are shown. Draw the structure of the compound. Hint: The chemical shift for a phenol OH signal can vary considerably.

46

Name: ______________________

ID: A

57. A compound with 3 degrees of unsaturation has the molecular formula C7 H1 0O. Its IR and 1 H NMR spectra are shown. Draw the structure of the compound.

58. Draw a mechanism for the following transformation. Include all curved arrows, necessary lone pairs, and nonzero formal charges.

47

Name: ______________________

ID: A

59. Predict the product of the following reaction and draw an arrow-pushing mechanism to rationalize its formation. Include all necessary lone pairs, curved arrows, and nonzero formal charges.

60. Predict the product of the following reaction.

61. Predict the product of the following reaction.

62. Predict the major organic product of the following reaction conditions.

63. Predict the major organic product of the reaction conditions shown here and draw a mechanism to rationalize its formation. Include all necessary lone pairs, curved arrows, and nonzero formal charges.

48

Name: ______________________ 64. Predict the product of the reaction sequence shown.

ID: A

65. Predict the product of the following transformation and draw a mechanism to rationalize its formation. Include all necessary lone pairs of electrons, curved arrows, and nonzero formal charges.

66. Draw a mechanism to illustrate the transformation shown here. Include all necessary lone pairs of electrons, curved arrows, and nonzero formal charges.

49