※ [本文轉錄自 NTU-Exam 看板] 作者: yuncheng42 (阿誠) 看板: NTU-Exam 標題: [試題] 94下 方俊民 有機化學 期中考 時間: Tue Apr 25 15:14:19 2006 課程名稱︰有機化學 課程性質︰必修 課程教師︰方俊民 開課系所︰醫技系、園藝系 考試時間︰2006/4/25 10:20~12:10 試題 : I. Simple choice(34%). There is only one correct answer in each question. 1. For a molecule of carbon monoxide (:C≡O:), (A) this molecule has positive charge (B) this molecule has negative charge (C) the carbon atom has positive formal charge (D) the carbon atom has negative formal charge. 2. The relationship between cyanate ion ¯O—C≡N and isocyanate ion O＝C＝N¯ is (A) resonance forms (B) constitutional isomers (C) configurational isomers (D) conformational isomers. 3. A sample of compound X (0.4 g) is dissolved in ethanol (10 mL) and placed in a tube of 10 cm in length. The observed optical rotation is +4.8, so the specific rotation [α] equals (A) +12 (B) +19.2 (C) +120 (D) +192. 4. The C—C bond length in benzene is about: (A) 1.21 A (B) 1.33 A (C) 1.39 A (D) 1.54 A. →A指的是埃 5. How many stereoisomers exist for 3-penten-2-ol? (A) 1 (B) 2 (C) 3 (D) 4. 6. Which compound has the highest reactivity toward electrophilic aromatic substitution? (A) phenol (B) toluene (C) chlorobenzene (D) nitrobenzene. 7. Which is the major product for the reaction of styrene (C6H5CH＝CH2) with HBr? (A) 1-bromo-1-phenylethane (B) 1-bromo-2-phenylethane (C) 1-bromo-2-ethenylbenzene (D) 1-bromo-3-ethenylbenzene. 8. Which sample will instantly discharge the brown color of Br2? (A) chlorohexane (B) 1-hexene (C) cyclohexane (D) benzene. 9. Which is the strongest nucleophile? (A) H2O (B) CH3S¯ (C)¯OH (D) CH3COO¯. 10. Which hydrocarbon can react with NaNH2 to form the hydrocarbon sodium salt? (A) 1-chlorobenzene (B) 1-chlorohexane (C) 1-hexene (D) 1-hexyne. 11. Butane and cyclobutane are (A) not isomers (B) constitutional isomers (C) configurational isomers (D) conformational isomers. 12. The bond angle of C—C—C bond in the chair form of cyclohexane is: (A) 60° (B) 90° (C) 109.5° (D) 120°. 13. According to the sequence rule, which substituent has the highest priority? (A) —CH(CH3)2 (B) —C(CH3)3 (C) —CH＝CH2 (D) —C≡CH. 14. Which of the following molecule is meso form? (A) (E)-1,3-dichloro-2-butene (B) (Z)-2,3-dichloro-2-butene (C) (2R,3S)-2,3-dichlorobutane (D) (2R,3R)-2,3-dichlorobutane. 15. Which compound most likely undergoes SN1 reaction on treatment with HCl? (A) 1-propanol (B) 1-propen-2-ol (C) phenol (D) 1,2-diphenylmethanol. ←老師打錯,更正為1,1-diphenylmethanol 16. Which reagent(s) are used to convert nitrobenzene to 1-bromo-3-nitrobenzene? (A) HBr (B) HBr/light (C) Br2/light (D) Br2/FeBr3. 17. Which organic bromide reacts fastest in SN2 reaction? (A) CH3Br (B) (CH3)2CHBr (C) (CH3)3Br (D) (CH3)3CCH2Br. II. (16%) Give IUPAC names (in English) for the following compounds. 1. ∣ ∣ 接起來 → ／∕＼／＼ 2. H NO2 ／＼︳／ ←接起來,連到H是虛線,連到NO2是粗線 ∣ ∣ ∣ ∣ ∣ ∣ ＼／︳＼ ←接起來,連到H是虛線,連到CH3是粗線 H CH3 3. ╲▁ ╱ ／／／ ←這是三鍵 ／ ≡— 4. O OH 雙鍵→ ＼＼╱ ∣ ／＼＼ ←雙鍵 ∥ ∣ ＼／／＼ ↑ Br 雙鍵 III. (6%) For the addition reaction of 2-methyl-1-propane (CH3)2C＝CH2 with HCl, 1. Why this reaction is an electrophilic reaction but not a nucleophile reaction? 2. By consideration of the stability of intermediates, explain why the reaction gives only 2-chliro-2-methylpropane but not 1-chloro-2-methylpropane. IV. (10%) The strictures of cis-1-tert-butyl-4-methylcyclohexane(A) and isomers (B) and (C) are shown. H3C ▁ ╲∕╱ 粗線→ ╲／ ＼∕←粗線 虛線→ ／＼▁／＼←虛線 H H cis-isomer (A) H3C ▁ ＼∕╱ 虛線→＼／ ＼∕←粗線 粗線→／＼▁／＼←虛線 H H (B) H CH3 ＼ ∕←虛線 粗線→＼∕▁ ＼∕╱ ／ ＼∕←粗線 ＼▁▁╱＼←虛線 H (C) 1. Draw the most stable conformation of cis-1-tret-butyl-methylcyclohexane(A). 2. Assign R/S notations to each of stereocenters in compound C. 3. Are compound A and B configurational isomers? 4. Are compound B and C constitutional isomers? V. (10%) Sighting along the C2-C3 bond of 2-methylbutane, there are two differert staggered conformations and two eclipsed conformations. 1. Draw the four conformations in Newman projections. 2. Indicate the most stable conformation. VI. (6%) Show the stereochemistry of products. 1. SN1 reaction of (R)-3-bromo-3-methylhexane with methanol to give 3-methoxy-3-methylhexane. 2. SN2 reaction of (S)-2-chlorobutane with sodium iodide to gives 2-iodobutane. 3. E2 reaction of (1R,2R)-1,2-dibromo-diphenylethane gives 1-bromo-1,2-diphenylethene. VII. (18%) Give structures of A - F incliding stereochemistry. (1) ╱╲ CH2Cl2 ﹨▁∕ + Br2 ———→ (A) — ↑這是雙鍵 O H3O+ ∥ (2) (B) + KMnO4 ———→ 2 ╱╲ H2SO4, HgSO4 (3) CH3CH2C≡CH + H2O ———————→ (C) Lindlar catalyst (4) H3C—C≡C—CH3 + 1 equiv. H2 —————————→ (D) (5) 雙鍵 O ↓ ∥ ／＼＼ ／＼ AlCl3 ∥ ∣ ∣ Cl —————→ (E) ＼╱╱＼／ ↑ 雙鍵 (6) 雙鍵 O ↓ ∥ ／＼＼／＼ HNO3, H2SO4 ∥ ∣ H ————————→ (F) ＼／／ ↑ 雙鍵 --

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