课程名称︰有机化学 课程性质︰医学系必修 课程教师︰陆天尧 开课学院： 开课系所︰ 考试日期（年月日）︰2011/06/23 考试时限（分钟）：110 是否需发放奖励金：是 感谢 （如未明确表示，则不予发放） 试题 : 上接 PART1 #1E1OaWRp 10. Which of the following cyclic hemiacetals would be formed when the open D-glucose undergo intramolecular cyclization to form the α-D-glucopyranose? ＣHO HO (仅画出正确结构) H┼OH ＼ HO┼H ╱\╲ \ Ｏ H┼OH HO \ ╲\╱ \ H┼OH \ \ ＣH2OH HO \ ╱\╲ \ H ＼\╱ \ ╲\╱ D-glucose OH | (open chain form) | OH 11. Formaldehyde (CH2O) is dissolved in water to give formalin (CH2(OH)2). What is the weight percent of formaldehyde in formalin? (A) about 30% (B) about 40% (C) about 50% (D) about 60% (E) about 70% 12. Cyclohexanone reacts with D2O in the presence of NaOD to give tetradeuteriocyclohexanone. / Ｏ Ｏ Ｏ /∣ ∥ D ∥ D \\ / ∣ ╱╲ NaOD ╲╱╲/ /¯/ ¯╲ ∣ ∣ ────＞ ╱∣ ∣╲ / ∣ ╲ ╲╱ D2O D ╲╱ D / ∣ ∕ ¯¯ ╲ ∕ ╲∕ XX Based on these conditions, how many protons in XX would undergo H/D exchange? [Hint: double bonds should be planar.] (A) 0 (B) 1 (C) 2 (D) 3 (E) 4 13. Propanal and butanal undergo aldol condensation followed by complete dehydration. How many of the following structures would be possible to obtain. Ｏ Ｏ Ｏ ╱ 　　　　 ∥ ∥ ∣　 　　 ∥ ∣ ╱╲╱ ╲╱ ╲╱ H ∥ ∥ ∥ ╲╱╲ ╲╱ ╲╱ Ｏ Ｏ Ｏ ∥ ∣ ∥ ∣ ∥ ╲╱ ╲╱ ╲╱ ∥ ∥ ∥ ╲ ╲╱ ╲╱╲ (A) 2 (B) 3 (C) 4 (D) 5 (E) 6 14. Concerning the ring formation from dimethyl pimelate shown below, which of the following statements would be FALSE? Hb Hb Hb Hb (b是下标) Ｏ Ｏ ╲╱ ╲╱　　　　　　　 MeO- ∥ ∥ ╱╲╱╲╱╲ ────＞ ╱╲╱╲ MeO2C CO2Me Δ ∣ ∣╲ OMe ╲╱ Ha (a是下标) (A) This reaction is an intramolecular condensation reaction. (B) Methanol is produced in this reaction. (C) Methoxide anion is not consumed in the reaction and can therefore be added in catalytic amount. (D) Using sodium ethoxide as the base would yield the same product. (E) Ha in the product would be more acidic than Hb in the starting material. 15. Which of the following compounds would have the most BASIC nitrogen atom? (A) (B) (C) NH2 NH2 NH2 ∕ ∕ ∕ 　 Ｃ—Ｃ Ｃ—Ｃ Ｃ—Ｃ //　　\\ // \\ 　//　　\\ Ｃ　　　Ｃ　　　 　 Ｃ Ｃ Ｃ　　　Ｃ \ / \ /　　　　　 \ / 　　　　　Ｃ＝Ｃ Ｃ＝Ｃ Ｃ＝Ｃ ∕ ∕ NO2 Cl (D) (E) Ｃ—Ｃ Ｃ—Ｃ // \\ ∕ // \\ ∕ Ｃ Ｃ—N—Ｃ Cl—Ｃ　　　Ｃ—N—Ｃ \ / H \\ \ / H \\ Ｃ＝Ｃ Ｏ Ｃ＝Ｃ Ｏ 16. (S)-1-methylcyclohexanone is treated with sodium ethoxide in ethanol until the equilibrium is reached: Ｏ CH3 0.1 eq ∥ / NaOEt ╱╲/...H ─────＞ ∣ ∣ EtOH ╲╱ Which of the following would be the ratio of (S) form to (R) form in the product? (A) 90:10 (B) 10:90 (C) 50:50 (D) 80:20 (E) 20:80 17. Which of the following compounds would show absorption in the UV-Vis spectrum at the LONGEST wavelength? [Hint: E=hc/λ, where h=Planck's constant, c=speed of light, λ=wavelength.] (A) (B) (C) (D) (E) ∥ ╲ ∥ ∣ ∥ ╲ ∥ ╲ ╲ ╲ ∣ ╲ ∣ ∣ ∥ ╲ ∥ ╲ ╲ ╲ ∣ ╲ ∥ ∣ ∥ To be continued ...... --

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