課程名稱︰有機化學 課程性質︰醫學系大一下必修 課程教師︰陸天堯 開課學院： 開課系所︰ 考試日期（年月日）︰2011/04/21 考試時限（分鐘）：110 是否需發放獎勵金：是 謝謝 （如未明確表示，則不予發放） 試題 : Organic Chemistry for Department of Medicine 2nd Midterm Examination April 21, 2011 10:20 a.m. - 12:10 noon Each of the following problems has 5 statements and only one statement is the correct answer. Each problem is worth 4 points. Any wrong guess will cost you 1 extra point. ¯¯¯¯¯¯¯¯¯¯¯¯¯ ¯¯¯¯¯¯¯¯¯ 1. How many of the following compounds would show aromatic character? ＿＿ ＿＿ // \\ H3Ｃ // \\ // \\ ∥╲＋ // \\ :Ｎ＝ＣH3 ╲ ╱ ∥ ＣH3 ╲ ╱╲ ∣ ∣ ╲╱ ∥╱ ╲╱ ╲ H3Ｃ—ＣH3 ＋　　　 H3Ｃ　 \\ // \\ // ¯¯ Ｈ ＿＿ Ｎ: // \\ 　 Ｃ—Ｎ　　　　 Ｃ—Ｃ　 ╱ ╲ // \\＿＿＿　　　 　// \\ // \\ Ｃ　　　Ｃ ╲ ╱ ＼╲ 　 Ｃ　　　Ｃ Ｃ　　　Ｃ // \\ ╲╱ 　＼╲ 　╲ ╱ 　　　╲ ╱ Ｃ Ｃ \\ /　　 　 Ｎ　　 Ｓ ╲ ╱ \\ /　　　 　Ｈ Ｃ＝Ｃ \\ / ╲ ╱╱ ╲╱ (A) 1 (B) 2 (C) 3 (D) 4 (E) 5 2. The Fischer projection formula of D-glucose is shown below. What is the perspective formula of D-glucose? ＣHO 僅列出正確型態 H-┼-OH H-┼-OH CHO HO-┼-H ﹨ H-┼-OH HC…OH ＣH2OH ∕ HO＞CH ﹨ HC…OH ∕ HO＞CH ﹨ CH2OH Considering the reaction below, answer question 3-5. ＣH3 Cl \\ ∕ 2HBr 　　 　H3Ｃ—ＣH ────＞ C5H9Br2Cl 　　 　　　　 ﹨ HＣ＝ＣH2 3. How many possible products including all possible stereoisomers can be obtained? (A) 4 (B) 5 (C) 6 (D) 7 (E) 8 4. How many pair(s) of enantiomers is (are) there in the mixture of products? (A) 0 (B) 1 (C) 2 (D) 3 (E) 4 5. How many possible products including stereoisomers is (are) in meso form? (A) 0 (B) 1 (C) 2 (D) 3 (E) 4 6. How many of the following reactions would give indicated product? H2O, H2SO4 Ｏ I CH3C≡CH ────────────＞ 　　∥ HgSO4 CH3ＣCH3 excess HBr II CH3C≡CH ────────────＞ CH3CHBrCH2Br excess Cl2 III CH3C≡CH ────────────＞ CH3CCl2CHCl2 CH2Cl2 1. H2/Lindlar cat. IV CH3C≡CH ────────────＞ CH3CHOHCH3 2. H2O, H2SO4 1. Na/NH3(liq) -78°C V CH3C≡CH ────────────＞ CH3CHOHCH3 2. BH3, HO-, H2O2, H2O (A) 1 (B) 2 (C) 3 (D) 4 (E) 5 7. (R)-2-iodopentane is treated with 0.1 equivalent of NaI in acetone until the equilibrium is reached. The products would be: Ｉ I ▼ 　　0.1 eq. NaI ︴ ╱╲╱╲ ───────＞ ╱ ╲╱╲ 　(R) (A) 90% (R)-2-iodopentane + 10% (S)-2-iodopentane (B) 80% (R)-2-iodopentane + 20% (S)-2-iodopentane (C) 50% (R)-2-iodopentane + 50% (S)-2-iodopentane (D) 20% (R)-2-iodopentane + 80% (S)-2-iodopentane (E) 100% (S)-2-iodopentane To Be Continued....... --

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