63. What is the major product of the following reaction? H2SO4 ? 

 
(A) I
(B) II
(C) III
(D) IV
(E) V

59. Which of these is the least reactive type of organometallic compound? (A) RK (B) R2Hg (C) RLi (D) R2Zn (E) R3Al

60. Which one of the following compounds will have the lowest wavenumber for carbonyl absorption? (A) I (B) II (C) III (D) IV (E) V  

【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. A student measured the optical activity of an unknown sugar at two different concentrations. The results of his measurements are shown below. Given that the sample cell had a path length of 10.0 cm, calculate the specific rotation for the unknown sugar.concentration                               observed rotation2.00 g sugar in 10.0 mL water              +159.1°  5.00 g sugar in 10.0 mL water              +127.8° (A) -10.5° (B) +25.6° (C) +79.5° (D) -104.5° (E) +256.2°

62. Which of the following series of synthetic steps could be used to carry out the transformation shown below?  (I) H2, Pt, (II) B2H6, (III) NaNO2, H3O , (IV) NaCN, HCl, (V) H2O2, NaOH (VI) PCC (A) I → II → V (B) IV → I → III (C) III → VI → V (D) II → V → III (E) None of the above

64. Which of the following sequences efficiently converts 2-methylpropene into 3-methylbutanal? (A) 1) HBr; 2) NaCCH; 3) O3; 4) H2O (B) 1) HBr; 2) NaCCH; 3) O3; 4) DMS(C) 1) HBr, ROOR; 2) NaCCH; 3) O3; 4) H2O (D) 1) HBr, ROOR; 2) NaCCH; 3) H2/Ni2B; 4) O3; 5) DMS (E) 1) NaCCH; 2) H2/Ni2B; 3) O3; 4) DMS  

65. How many positive and negative peaks appear in the DEPT-135 and in the DEPT-90 spectrum of 2-methylpentane? (A) DEPT-135: two positive and one negative, DEPT-90: one positive (B) DEPT-135: three positive and two negative, DEPT-90: one positive (C) DEPT-135: three positive and two negative, DEPT-90: no signals (D) DEPT-135: two positive and three negative, DEPT-90: two positive (E) None of the above is correct

66. The Fischer indole synthesis is the reaction of phenylhydrazine with a carbonyl compound to give the corresponding indole. For the preparation of the following indole, what carbonyl compound is needed?  (A) I (B) II (C) III (D) IV (E) V

67. What is the major product obtained from the following reaction sequence?  (A) I (B) II (C) III (D) IV (E) V

68. Which of the following compounds can adopt a chair conformation in which there are no axial methyl groups?(A) 1,1-dimethylcyclohexane(B) cis-1,2-dimethylcyclohexane (C) trans-1,2-dimethylcyclohexane (D) trans-1,3-dimethylcyclohexane (E) everyone above have no axial methyl group

69. For the following reaction sequence, which molecule is an expected major product?