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101 年 - 101 學士後西醫：有機化學#27197　

1.I. Choose one correct answer for the following questions 【單選題】每題 1 分，共計 60 分，答錯 1 題倒扣 0.25 分，倒扣至本大題零分為止，未作答，不給分亦不扣分。1. According to atomic theory:
(A) The nucleus is positively charged
(B) The nucleus contains both charged and uncharged particles
(C) The electrons contribute very little to the total mass of the atom
(D) The electrons are located in the atomic space outside the nucleus
(E) All of the above.

2.2. A coenzyme frequently encountered in transamination reactions is
(A) Tetrahydrofolate
(B) Pyridoxal phosphate
(C) Thiamine pyrophosphate
(D) Biotin
(E) NADH

3.3. Which one of the following structures represents a different compound from the other three?

(A) 1
(B) 2
(C) 3
(D) 4
(E) All of the above are the same.

4.4. Which of the standard amino acids is achiral?

(A) Lysine
(B) Proline
(C) Valine
(D) Alanine
(E) Glycine

5.5. Which of the following Newman projections does not represent 2-methylhexane?

(A) 1
(B) 2
(C) 3
(D) 4
(E) both 2 and 3

6.6. 2,3-Dibromobutane can exist three stereoisomers as shown below. What stereoisomers would be formed by the following reaction?

(A) 1 only
(B) 2 only
(C) 3 only
(D) 1 and 2
(E) 2 and 3

7. In the following structures, the protons pointed by arrow (on C2) which belong to diastereotopic hydrogens.
(A)
(B)
(C)
(D)
(E) None of the above.

8.8. What is the correct IUPAC systematic name for the following compound?

(A) 1,2-Dichlorocyclohexene
(B) 2,3-Dichlorocyclohexene
(C) 1,6-Dichlorocyclohexene
(D) 1,2-Dichloro-2-cyclohexene
(E) None of the above.

9.9. What is the formal charge on the nitrogen atom indicated with the arrow in the following compound?

(A) 0
(B) −1
(C) +1
(D) −2
(E) +2

10.10. Which of the following nucleophiles reacts with MeI in greatest rate in an aqueous solution?
(A) Me

(B) MeOH
(C) HO

(D) CH₃CO₂

(E) MeS

11.

11. Which of the following compounds would have a greater dipole moment than you expect?
(A)
(B)
(C)
(D)
(E) None of the above.

12.12. Compound A: M+ = 86, IR absorption: 3400 cm^-1, ¹³C NMR spectral data: Broadband-decoupled ¹³C NMR: δ 30.2, 31.9, 61.8, 114.7, 138.4, DEPT-90: δ138.4; DEPT-135: δ138.4, negative peaks at δ 30.2, 31.9, 61.8, 114.7. What is the structure of compound A?

13.13. In the following, which one is the most acidic compound?

(A) 1
(B) 2
(C) 3
(D) 4
(E) 2 = 3

14.14. Compound I has a molecular formula C5H10O, and 1H-NMR data shown below: δ 0.95 (d, J = 7 Hz, 6H), 2.10 (s, 3H), 2.43 (m, 1H). What structure fits compound I?

15.15. What is the coupling constant for the Ha and Hb protons in the 1 H NMR spectra of the following compound?

(A) 0 Hz
(B) 3 Hz
(C) 7 Hz
(D) 10 Hz
(E) 15 Hz

16.16. Which of the following orbital represents the HOMO of 1,3-butadiene in ground state?

17.

17. Which of the following dienes would not react with a dienophile in a Diels-Alder reaction?
(A)
(B)
(C)
(D)
(E) None of the above.

18.18. Arrange the following compounds in order of increasing reactivity to electrophilic aromatic substitution reaction.

(A) 2<3<4<1<5
(B) 1<2<4<3<5
(C) 2<4<1<3<5
(D) 2<1<4<3<5
(E) 2<4<1<5<3

19.

19. Which of the following reactions could not produce the desired product?
(A)
(B)
(C)
(D)
(E) None of the above.

20.20. Select the most reasonable formula for the compounds with the following mass spectral data: M⁺ at m/z 101 with a minor M+1 peak.
(A) C₅H₉Cl
(B) C₅H₁₂N₂
(C) C₆H₁₅N
(D) C₉H₁₂O
(E) C₆H₉S

21.21. What reagent should be used for the following reaction? ?

(A) CH₃CH₂MgBr
(B) CH₃CH₂Li
(C) (CH₃CH₂)₂Zn
(D) CH₃CH₂B(OH)₂
(E) (CH₃CH₂)₂CuLi

22.22. Which of the following alkenes is most reactive toward ozonolysis?

23.23. Which of the following ketones show strong characteristic band at 1815 cm-1?

24.24. In aromatic nitration reactions, nitric acid (HNO3) is used in conjunction with the stronger acid, sulfuric acid, H2SO4, to form an intermediate. Which of the following could be the formula for this intermediate?
(A) NO₃

(B) H₃SO₄

(D) HNO₂
(E) NO

25.25. What is the best reagent for the following reaction? Ph OH OH Ph OH ?

(A) PCC
(B) Na₂Cr₂O₇, H₂SO₄
(C) DMSO, (COCl)₂ then Et₃N
(D) MnO₂
(E) H2CrO4

26.26. What is the major product of the following reaction?

(A)

(B)

(C)

(D)

(E) None of the above.

27.27. What product would be obtained by the following reaction?

(A)

(B)

(C)

(D)

(E) None of the above.

28.28. Which fragment would you expect to be the base peak in the mass spectrum of limonene?

(A) m/z = 136
(B) m/z = 121
(C) m/z = 93
(D) m/z = 68
(E) m/z = 49

29.29. What is the major product of the following reaction? ?

30.30. Which of the following would correctly describe the respective 13C NMR and 1 H NMR spectra for the indicated atoms for the compound shown below?

(A) Atom 1 would produce a peak at 205 ppm and atom 2 would appear as doublet
(B) Atom 1 would produce a peak at 175 ppm and atom 2 would appear as a singlet
(C) Atom 1 would produce a peak at 205 ppm and atom 2 would appear as a triplet
(D) Atom 1 would produce a peak at 175 ppm and atom 2 would appear as a triplet
(E) Atom 1 would produce a peak at 175 ppm and atom 2 would appear as a doublet

31.31. What is the major product of the following reaction?

32.32. What is the major product of the following reaction?

(A)

(B)

(C)

(D)

(E) None of the above.

33.33. How would you carry out the following transformation?

(A) 1. (a) NaOH, (b) CH3CH2Br; 2. Na, NH3(l)
(B) 1. Na, NH3(l); 2. (a) CH3MgBr, (b) CH3CH2Br
(C) 1. (a) NaNH2, (b) CH3CH2Br; 2. H2, Lindlar’s catalyst
(D) 1. (a) NaNH2, (b) CH3CH2Br; 2. Na, NH3(l)
(E) 1. (a) BuLi, (b) CH3CH2Br; 2. H2, Lindlar’s catalyst

34.34. What is the best reagent for the following transformation?

(A) HF
(B) CuF
(C) HBF₄
(D) Bu₄NF
(E) F₂

35.35. What product would you expect of the following transformation?

36.36. In the following reaction, what is the major product?

37.37. In the following reaction, which compound is the major product?

(A) No reaction

38.38. Which of the following reagents could not be applied to the following transformation?

(A) HgCl₂, CaCO₃, acetone
(B) NiCl₂, NaBH4, DMF
(C) Raney-Ni, EtOH
(D) n-Bu₃SnH, AIBN, benzene
(E) All of the above work well.

39.39. What is the final product of the following reaction?

(A)

(B)

(C)

(D)

(E) None of the above.

40.40. In the following reaction, what is the major product?

41.41. What is the best reagent for the following transformation?

(A) 1. PhMgBr, ether 2. H₃O

(B) PhCH₂MgBr, ether 2. H₃O

42.42. In the following reaction, which compound is the major product?

43.43. What is the final product of the following sequential reactions?

44.44. In the following reaction, which compound is the major product?

45.45. In the following reaction, what is the major product?

46.46. In the following reaction, which compound is the major product?

47.47. The following substance is heated in the presence of aqueous NaOH. The product of the reaction is:

(A)

(B)

(C)

(D) Both B and C
(E) All of the above.

48.48. In the following reaction, which compound is the major product?

49.49. In the following reaction, which compound is the major product?

50.50. Which reagent would be best suited for the transformation shown?

(A) alkaline Cu²

in H₂O
(B) Ag

in H₂O/NH₃
(C) H₂, with Ni catalyst
(D) NaNO₃ at 0°C
(E) NaBH₄ in H₂O

51.51. In the following reaction, which compound is the major product?

52.52. In the following reaction, what is the major product?

53.53. In the following reaction, which compound is the major product?

54.

54. Which of the following reaction is called Suzuki-Miyaura coupling reaction?
(A)
(B)
(C)
(D)
(E) None of the above.

55.55. In the following reaction, which compound is the major product?

56.56. In the following reaction, which compound is the major product?

(A)

(B)

(C)

(D)

(E) None of the above.

57.57. In the following reaction, which compound is the major product?

58.58. In the following reaction, which compound is the major product?

59.59. What type of intermediate is present in the following reaction?

(A) Carbocation
(B) Carbanion
(C) Free radical
(D) Carbene
(E) This reaction has no intermediate.

60.60. The following reaction is an example of the Ugi-Heck reaction. What product can be produced?

61.【單選題】每題 2 分，共計 40 分，答錯 1 題倒扣 0.5 分，倒扣至本大題零分為止，未作答，不給分亦不扣分。61. List the following esters in order of decreasing reactivity in the first step of a nucleophilic acyl substitution reaction:

(A) 2>3>1>4
(B) 4>1>3>2
(C) 2>4>1>3
(D) 3>1>4>2
(E) 4>2>1>3

62.62. The chiral centers in the structure of penicillin V are indicated ( C-2, C-5, and C-6). In the following assignments which one is wrong?

(A) 2S
(B) 5R
(C) 6R
(D) 6S
(E) None of the above.

63.63. What is the structure of the final product?

64.64. What is the structure of the final product?

65.65. What is the major product of the following four components’ reaction?

66.66. In the following reaction, which compound is the major product?

67.67. What is the major product of the following reaction?

(A)

(B)

(C)

(D)

(E) None of the above.

68.68. In the following reaction, which compound is the major product?

69.69. What is the final product of the following sequential reactions?

70.70. Consider the reaction given below, which of the following is not applicable to this reaction?

(A) An example of cycloaddition reaction
(B) Bond formation is suprafacial
(C) Bond formation is antarafacial
(D) Prefer under thermal conditions
(E) All of these apply to this reaction.

71.71. In the following reaction, which compound the major product?

72.72. In the following sequential reactions, what is the final product?

73.73. What is the structure of the final product?

74.74. How could the following transformation be accomplished?

(A)

(B)

(C)

(D)

(E) All of the above.

75.75. In the following reaction, which compound is the major product?

76.76. In the following reaction, which compound is the major product?

77.77. Photochemical reaction of 7-dehydrocholesterol to vitamin D3 involves two types of pericyclic reactions. What are those?

(A) Electrocyclic reaction and sigmatropic rearrangement
(B) Electrocyclic reaction and ene reaction
(C) Cycloaddition and electrocyclic reactions
(D) Cycloaddition reaction and sigmatropic rearrangement
(E) Ene reaction and sigmatropic rearrangement.