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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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