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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.

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

a. d.

b. e.

c.

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

a. ketone d. alcoholb. carboxylic acid e. alkane

c. amine

____ 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 1H NMR

spectrum for this molecule?

a. 0 d. 3

b. 1 e. 4

c. 2

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

a. d.

b. e.

c.

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

a. 2

b. 3

c. 6

d. 7

e. There is insufficient information to answer the question.

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

a. d.

b. e.

c.

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

a. d.

b. e.

c.

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

a. d.

b. e.

c.

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

a. d.

b. e.

c.

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

a. d.

b. e.

c.

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

a. d.

b. e.

c.

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

a. d.

b. e.

c.

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

a. LiAlH4, then H3O+ d. H2, Pd/C

b. NaBH4 in methanol e. CH3MgBr and H3O+

c. 1. CH3MgBr

2. H3O+

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____ 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 thefinal product of this reaction?

a. d.

b. e.

c.

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

a. HIO4 d. KMnO4

b. H2SO4 e. NaBH4

c. O3

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

a. d.

b. e.

c.

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

a. d.

b. e.

c.

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____ 23. Predict the product of the following reaction.

a. d.

b. e.

c.

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

a. O3, then H2O2 d. NaOH, H2O, then H3O+

b. KMnO4 and H2O e. Either a or bc. O3, then (CH3)2S

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____ 25. Predict the major organic product of the following reaction.

a.

b.

c.

d.

e.

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

a. d.

b. e.

c.

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____ 27. What is the product of the following reaction?

a.

b.

c.

d.

e. No reaction would occur.

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

a.

b.

c.

d.

e.

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

a. I d. II, III, and V

b. II and III e. I and IV

c. II, III, and IV

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

a.

b.

c.

d.

e.

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____ 31. Which of these structures is not a mechanistic intermediate in acid-catalyzed esterification of a

carboxylic acid?

a. d.

b. e.

c.

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____ 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. NaBH4 d. H2

b. LiAlH4 e. H3O+

c. DIBAL-H

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

a. d.

b. e.

c.

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

a. d.

b. e.

c.

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

a. H2/Pd or Raney Ni/H2 d. NaBH4 in methanol solvent

b. LiAlH4, then H2O e. Both b and c

c. Br 2, then H2O and heat

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____ 37. Predict the major organic product of the following reaction.

a. d.

b. e.

c.

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

a. d.

b. e.

c.

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

a. d.

b. e.

c.

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

a. d.

b. e.

c.

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

a. d.

b. e.

c.

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

a.

b.

c.

d.

e.

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

a. d.

b. e.

c.

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

a.

b.

c.

d.

e.

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____ 45. What is the product of this reaction?

a. d.

b. e.

c.

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

a. d.

b. e. None of these is the product of the

conditions shown.

c.

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

a. d.

b. e. Either c or d can form.

c.

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____ 48. What is the product of this reaction?

a. d.

b. e.

c.

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____ 49. What is the product of this reaction?

a. d.

b. e.

c.

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

a. d.

b. e.

c.

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Short Answer

51 . Match the three compounds shown here to the three IR spectra.

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

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

54. The IR, 1H NMR, and mass spectra for a compound with molecular formula C 7H1 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.

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55 . Match each of these 1H NMR spectra to the correct compound. Then assign each signal in both spectra

to the corresponding hydrogen(s).

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56 . A compound with 4 degrees of unsaturation has the molecular formula C1 0H1 4O. Its IR and 1H NMR

spectra are shown. Draw the structure of the compound.

Hint: The chemical shift for a phenol OH signal can vary considerably.

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57 . A compound with 3 degrees of unsaturation has the molecular formula C7H1 0O. Its IR and 1H 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.

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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.

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64 . Predict the product of the reaction sequence shown.

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.