Additional Multiple Choice Questions Volume 2

1. What is the major product obtained from the following reaction?

2. Which of the following reactions would provide the best synthesis of 2-butanol?

3. Which reagent would provide the product shown?

4. Which reagent would provide the product shown?

5. What is the major product obtained from the following reaction?

6. What is the major product obtained from the following reaction?

7. What is the major product obtained from the following reaction?

8. Which of the following compounds is methyl propanoate?

9. What is the major product obtained from the following reaction?

10. Which of the following is an intermediate in the acid hydrolysis of an ester?

11. Which of the following would be the product of the initial protonation of an amide?

12. A mixture of toluene, benzoic acid, aniline and phenol was dissolved in diethyl ether and extracted with 5% NaHCO3 solution.  This extract was acidified until a white crystalline compound appeared. What is the identity of this compound?

13. What is the major product obtained from the following reaction?

14. Which of the following would be the best synthesis of the acid shown below?

15. Which of the following carbocations would have the greatest stability?

16. Which of the following compounds would exhibit aromatic properties?

17. Which of the following will react more rapidly with BF3?

(a) A

(b) B

(c) Both have the same basicity because the number of alkyl groups are equal.

18. The beta alkene carbon atom (marked with a star) of the following compound will have a chemical shift in the carbon NMR spectrum _?_  than the normal shift for ethene (H2C=CH2) primarily due to _?_.

(a) greater…inductive and/or anisotropic effects

(b) less… inductive and/or anisotropic effects

(c) greater…resonance effects

(d) less…resonance effects

19. The beta alkene carbon atom (marked with a star) of the following compound will have a chemical shift in the carbon NMR spectrum _?_  than the normal shift for ethene (H2C=CH2) primarily due to _?

(a) greater…inductive and/or anisotropic effects

(b) less… inductive and/or anisotropic effects

(c) greater…resonance effects

(d) less…resonance effects

20. Which of the following molecular orbital diagrams for butadiene represents the highest occupied molecular orbital in the excited state?

21. Which of the following compounds would yield the following set of multiplets in its proton magnetic resonance spectrum?

22. The following IR Spectrum best represents which of the following compounds?

23. The following pmr spectrum represents which of the following compounds?

24. Which of the following compounds will show the greatest downfield shift for the methyl absorption in PMR?

25. Which of the following C-F bonds will absorb light in the infrared at the larger wavenumber?

26. The reason that the chemical shift for an alkyne hydrogen atom is upfield from an alkene hydrogen atom is that…

(a) the alkyne carbon has a greater relative electronegativity due to the fact that it is sp hybridized.
(b) there are 2 pi bonds for resonance in the alkyne versus only 1 pi bond in the alkene.
(c) the anisotropic effect of the triple bond shields the alkyne hydrogen atoms whereas the anisotropic effect of the double bond deshields the alkene hydrogen atoms.
(d) it is more acidic than the alkene hydrogen atoms.

27. Which of the following will be the most abundant fragment ion formed from 2-butanone in the mass spectrum?

28. Which of the following will be the most abundant fragment ion formed from H2NCH2CH2OH in the mass spectrum?

29. What is the major product obtained from the following reaction?

30. Which compound will react most readily in a SN1 reaction?

31. What is the major product obtained from the following reaction?

32. What is the major product obtained from the following reaction?

33. If the following 13C labeled compound undergoes the following reaction, which product would be obtained? The 13C carbon is marked with a star.

34. Which of the following compounds will react most rapidly in an E2 reaction?

35. What is the major product obtained from the following reaction?

36. What is the major product obtained from the following reaction?

37. What is the major product obtained from the following reaction?

38. What is the major product obtained from the following reaction?

39. What is the major product obtained from the following reaction?

40. What is the major product obtained from the following reaction?

41. What is the major product obtained from the following reaction?

42. What is the major product obtained from the following reaction?

43. What is the major product obtained from the following reaction?

44. What is the major product obtained from the following reaction?

45. How many dichloro isomers can be obtained from the following reaction?

(a) 1                        (b) 2                        (c) 3                    (d) 4

46. What is the major product obtained from the following reaction?

47. What is the major product obtained from the following reaction?

48. What is the major product obtained from the following reaction?

49. What is the major product obtained from the following reaction?

50. What is the major product obtained from the following reaction?

51. What is the major product obtained from the following reaction?

52. What is the major product obtained from the following reaction?

53. What is the major product obtained from the following reaction?

54. What is the major product obtained from the following reaction?

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Copyright © April 2002 by Richard C. Banks...all rights reserved.