課程名稱︰有機化學 課程性質︰醫學系必修 課程教師︰陸天堯 開課學院： 開課系所︰ 考試日期（年月日）︰2011/06/23 考試時限（分鐘）：110 是否需發放獎勵金：是 感謝 （如未明確表示，則不予發放） 試題 : 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 (僅畫出正確結構) 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是下標) Ｏ Ｏ ╲╱ ╲╱　　　　　　　 MeO- ∥ ∥ ╱╲╱╲╱╲ ────＞ ╱╲╱╲ MeO2C CO2Me Δ ∣ ∣╲ OMe ╲╱ Ha (a是下標) (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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