課程名稱︰有機化學丙 課程性質︰ 課程教師︰劉緒宗 開課學院：生農 開課系所︰獸醫 植微 考試日期（年月日）︰2013/03/28 考試時限（分鐘）：兩節課 是否需發放獎勵金：是 （如未明確表示，則不予發放） 試題 : 1.Provide the correct name for the following compounds(in English)(20) (A) ╱╲╱╲╱╲╱ (B) ╲ (C) H3C╲ ∣ ｜ C＝ ╱╲╱╲╱╲ H3C╱ 　　　　Br (D) 　　　＼╴ (E) ╴╴ (F) 　　　╱ 　　　　　╱　∥ ,,,,╱ ╲▲ 　　＝ 　　　　　╲　∥ ╲ ╱ 　　　 ╲╱　╲ 　　　　　　￣　╲ ￣￣　　　　　　　｜　 (G) (H)　　　　　　　　　 (I)　 　　　▽ Cl F —≡ 　　　∣ ∣ ∣ ∥ 　╲╱╲╱╲　　 　╲╱╲╱╲＝ ￣ 　　　　　　　　　　　　　　　　　 (J) ＝ ╲ 　　　 ╱ ＝　　＝ ╱　╲╱ ╲ 2.Please draw all possible staggered conformations (in Newman projections) wuth respect to C2-C3 of pentane and indicate the most stable one.(10) 3.Draw all possible chair conformations of the following, and which is the more stable one.(10) (A)▲╴╴ (B) ╴╴ ╱ ╲,,,╱ ╱ ╲,,, ╲╴╴╱ ╲ ▼╲╴╴╱ ▼ ▼ 4.Classify the following species into Nucleophile, electrophile and Lewis acid.(10) + ╴╴ ╴╴ BF3 　 ╱￣￣　　Me－C≡C¯ Cl¯ K ╱ ╲ ｜ ｜╴ 　 ＝　　　　　 < NH ╲╱+ ╲╴╴╱ 5.Assign R,S configurations to the chiral center in the molecules below.(10) ▲╴╴ CHO H2N ╱ 　Ｏ ｜ ｜ <　　 ︳　 HO —｜—H —｜—C≡N ╲　╴╴︳,,,,╱ ｜ ｜ 　　Ｏ CH2OH H CH3 HOOC ｜ OH ╲▃▄｜▄▂╱ ◢██｜██◣ ███｜███ ██ ╱╲ ██ ◥ ╱██╲ ◤ ╱▂ ▂╲ H ￣∥ ▅▅ CH3 O ∣ ｜ CH3 6.Using electron flow to show the reaction pathway of the polomerization of vinylbenzene (CH2=CH-C6H5) initiated by ROOR.(10) 7.Suggest reagents or structures of organic products for the following reactions.(20) H2SO4 (A) H3C-C=CH2 —————> ｜ CH3OH CH3 　　　 ＝　 Cl2 (B) ╱ ︳ —————> ╲╴︳ (C) 1.NaNH3 ▽﹣C≡C-H —————> 2.CH3Br (D) + D2O ▽-≡C¯Li —————> (E) ╴╴ ︱ ╲ H2SO4 ︱ >-C≡C-H —————> ︱ ╱ H2O ￣￣ (F) CH3Li + H-N-CH3 —————> ∣ CH3 (G) ╴ ╴╱ ╲　　 HBr ｜ ╲　╱　　—————> 　 ｜ ╱＝ 　　￣ (H) excess HBr ▽-C≡C-H —————> (I) ╴╱ ╱ ∥ H2 ╲ ∥ —————> ￣╲ Pd/C (J) excess H2 C≡C—C＝C —————> Pt/C 8.Show how to carry out the following transformation using the given starting material and any necessary reagents.(10) ? (A)H—≡—H —————> ╱╲╱ ｜ Cl ? OCH3 (B)H3C—≡—H —————> ╲╱ ｜ 9.Please draw the correct structure of (S)-2-bromobutane in Fischer projection.(4) Good luck! --

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