推 ALegmontnick:優秀! 10/21 18:44
推 hsnukevin :圖好精美XD 10/24 21:08
課程名稱︰有機化學乙上
課程性質︰必修
課程教師︰劉緒宗
開課學院：工學院
開課系所︰化工系
考試日期（年月日）︰2010/10/21
考試時限（分鐘）：120
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(20)
(A) ＼╱ (B) ∣ (C) CH3 (D) ＿╱ I (E)
∣ ／＼／＼／＼ ▕ I ＿/ ╲╱ ╱╲▁
／＼／＼／＼／ ∣ ∣ H3C—C—CH3 ∣ ∣ '''╲╱
▕ ＼ ╱
CH3
(F) (G) (H) ＿ (I) ＿ (J) F F
╱╲╱ ∣ ＿ ∕ ﹨ ∣ ∣
CH2Cl2 ∣ ╲╱╲╱ / ＼∕╲╱ ╱╲╱╲
▲ ∣ ∣ ∣
╲ ╱ F
2.Draw the two chair conformations of the following compound, and tell which
is more stable, why?(6) HO
▼＿
▁╱ ╲▁∠
╲＿╱ ﹨
3.Please draw all possible staggered conformation (in Neuman projections) with
respect to C2-C3 of butane. Indicate (i) which has Gauche interaction
(ii)which is in the lowest energy?(6)
4.Classify the following species into Nucleophile, Electrophile, Lewis acid and
Lewis base.(12)
⊕ ⊕ Θ
H NH3 BF3 Na H3C: H3C—≡—CH3
5.Structure of bicyclo[2.2.1]heptane is shown below. Please draw the
Neuman projection along C2-C3 and show all the torsional strain.(6)
7
▕﹨ 4
5 ＿▕_﹨＿＿3
▕ ▕＿＿＿/
▕ ／1 2
▕／
6
6.Assign R,S configurations to indicated chiral center in the molecules below.
(15) NH2
H CH3 │ (D)?
│ │ (C)? │↙
H2N ＿＿│＿＿ CH3 │↙ HOOC──┼──H
╲ ╱ │ ╲ ╱ HO──┼──CH2OCH3 │
╲ ╱ │ ╲╱ │ H──┼──NH2
∕ │ ﹨ │ │
∕ (A)?│ ﹨ CH2OH │
| ↘│ | COOH
| ⊙ |←(B)? O (E)?
| ╱ ＼ | ∥ ↙
﹨ ╱ ＼ ∕ ╱╲,,,∕
H ﹨ ╱ ＼ ∕ ∣ ∣ ﹨
╲ ╱ ＼ ╲_o
╲╱ ╲＿＿＿＿＿ ╱ ＼
∥ ∣ OH
∥ ∣
O H
7.Reaction of CH3CH3 with Cl2 under irradiation of light yields CH3CH2Cl.
Provide the detail mechanism of this reaction.(10)
8.Conformational exchange is shown below. Please tell which is more stable,
and by? kcal/mol.
Br Explain your answer
∣ ∣ ＿
∕╲ ╱/ \╲ ╱﹨ 1,3-diaxial interaction of
∕ ╲╱∕ ——→ ﹨╲╱ ﹨
Br ∕╱╲ ∣∕ ←—— ﹨ ╱╲﹨ Br←→H 0.25kcal/mol (6)
╲/╱ ╲∕ ﹨╱ ╲\╱
9.How would you resolve the racemic mixture of a? Please use scheme to show the
detail procedurea.
COOH COOH
∣...H H...∣
╱▼ ▼╲
HO Et Et OH
╰───╮───╯
a (10)
10.Please draw the structure of (R)-2-bromobutane in Fischer projection.(5)
。
11.The specific optical rotation of an organic compound A is +120 .
What would be th specific optical rotation value of a solution containing
60% A and 40% of its mirror image?(4)
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