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

63. What is the major product of the following reaction? H2SO4 ?  (A) I (B) II (C) III (D) IV (E) V

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? 

70. Which of these is NOT a useful method for the synthesis of 1,3-pentadiene?(A) 1,4-pentanediol + H2SO4 at 180o C (B) 2,4-dibromopentane + (CH3)3COK , (CH3)3COH at 75o C (C) 2,4-pentanediol + H2SO4 at 180o C (D) HC=CCH=CHCH3 + H2, Ni2B (P-2)(E) 1,4-dibromopentane + CH3CH2ONa , CH3CH2OH at 75o C

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