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）︰2011/06/23 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 Final Examination June 23, 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. Which of the following compounds does NOT exhibit the keto-enol tatuomerism? (A) ／＼╱＼／ (B) N—N (C) Ｏ Ｏ (D) Ｏ　Ｏ　 (E) C—N ∣○∣ ∥ // \\ ∥ ∥ ∥　∥ // \\ ＼／ Ｏ ＼　／＼　　 　 ／＼／＼　 ／＼／＼　　 ＼ ／ 　　　 　　　　　　 Ｎ　　CH3 ∣ Ｎ 　　　　 Ｈ　 　　　　　　　　　　　　　　　　　　　　 ﹨ CH3 2. Which of the following reactions would NOT take place? (A) ﹨ H2O ﹨ C＝O ＋ LiAH4 ───＞ C—OH ∕ ∕ (B) ﹨ ﹨ C＝O ＋ H2NOH ───＞ C＝N—OH ∕ ∕ (C) ﹨ ﹨ C＝O ＋ CH3Br ───＞ C—O—CH3 ∕ ∕ (D) ﹨　　　　　　　　OH- ﹨ C＝O ＋ HCN ───＞ C—O—H ∕ ╱﹨ Ｃ≡N (E) ﹨ ﹨ C＝O ＋ RMgBr ───＞ C—O—MgBr ∕ ／﹨ Ｒ 3. Which of the following would be the product of the reaction sequence below? Ｏ H3Ｃ—ＣH3 ╱¯╲ ∥ ∕ 　 ﹨ HO OH Mg H3C-Ｃ-H H+, H2O Br CH C＝Ｏ ──────＞ ──＞ ─────＞　─────＞ ＼ ／ ＼ ╱ cat. amount ＣH3 ＣH3 of HCl (這題大家就當填充吧....化合物全畫出來會死人......底下僅提供正解圖) 　 Ｃ OH ／ ＼ ╱╲╱ Ｏ＝Ｃ 　Ｃ ∣ ﹨ ∕ 　　　 C—C　 4. The conversion of a carbonyl compound to an enolate depends on the pKa corresponding carbon acids. Considering 1,3-cyclohexanedione, which of the following statements would be FALSE? H H ＼／ pKa~10 Ｏ- Ｏ Ｃ　 Ｏ ﹨ \\╱ ╲// Ｃ＝Ｃ 　 Ｃ Ｃ ∕　　﹨ ∣　 ∣ Ｃ Ｃ—Ｏ- H2Ｃ　　Ｃ—H 　﹨　　// ＼ ／﹨ pKa~25 Ｃ—Ｃ H2Ｃ H 1,3-cyclohexanedione dienolate (A) An alkoxide ion is used to remove the α-proton with lower pKa value. (B) Addition of one equivalent of the alkoxide ion then one of the BuLi would produce a dienolate. (C) Reaction of 1,3-cyclohexanedione with 2 equivalents of BuLi would give dienolate. (D) Reaction of the enolate prepared from (A) with methyl iodide would give 2-methyl-1,3 cyclohexanedione. (E) Reaction of dienolate described above with methyl iodide would give 4-methyl-1,3-cyclohxanedione Methyl Orange, a water soluble dye CC and related compounds can be synthesized by the following reaction scheme. Answer questions 5 and 6. ＮH2 +Ｎ2 ﹨ ∣ ∣ :N—(phenyl group) ／＼ ? ／＼ ∕ 　 ∣○∣ ───＞ ∣○∣ ──────────＞ water soluble dye CC ＼／ ＼／ ∣ ∣ ＳO3H ＳO3H AA BB 5. Which of the following reagents would convert AA to BB? (A) HCl (B) HNO3, H2SO4 (C)H2SO4 (D) NaNO2, HCl (E) NaNO2, NaOH 6. Which of the following would likely be the structure of CC? (嗯...抱歉...當作填充題吧) HO3S—(苯環)—Ｎ \\ ∕ 　 　　　　　　　　 Ｎ—(苯環)—Ｎ ﹨ 7. Which of the following would NOT readily undergo decarboxylation upon heating? (A) (B) (C) Ｃ ＣOOH Ｏ Ｏ Ｏ Ｏ ╱ ╲ ／ ∥ ∥ ∥ ∥ Ｃ　　Ｃ—ＣOOH ╱╲／＼ ╱╲╱╲╱╲ ∣ ∣ H3CＯ ∣ OH ∣○∣　　　ＯH Ｃ　　Ｃ ╱ ＼／＼ ╲　╱ ∥ ∣○∣ 　　　 　 Ｃ　(環上H省略) ＼／ (D) (E) Ｏ Ｏ　Ｏ ∥ OH ∥ ∥ ╱╲╱╲╱ ╱╲╱╲ \＿/ ∥ ∣ OH Ｏ ╱╲ ∣ ∣ ╲╱ AA reacts with methyl methanoate (HCOOCH3) in the presence of methoxide anion to give compound BB, which on treatment with aqueous acid and gentle heating, will decarboxylate to form butanol. Answer questions 8 and 9. 8. Which of the following compounds shown below would be compound BB? (A) (B) (C) Ｏ CO2Me ╲╱╲ ∣ ∥ ╱╲╱ ∥ CO2Me ╱╲╱╲ ╱ ∣ Ｏ ∣ Ｏ ＣOOH ＣO2Me (D) (E) COOH CO2ME ╱╲╱ ╱╲╱ ∣ ∣ ＣHO ＣHO 9. Which of the following compounds shown below would be compound AA? (A) (B) (C) Ｏ Ｏ ∣ ∥ ∥ ╱╲╱╲ ╱╲╱╲ ╱ ╱╲ ╱╲ Br Ｏ　　　　　　 Ｏ (D) (E) Ｏ ∥ ╲╱╲ ╱╲╱╲ ╱ ∣ Br Ｏ To be continued.... --

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