課程名稱︰有機化學乙上 課程性質︰必帶 課程教師︰陳昭岑 開課學院：工 開課系所︰化學工程學系 考試日期（年月日）︰101/10/18 考試時限（分鐘）：110 mins 是否需發放獎勵金：是 （如未明確表示，則不予發放） 試題 : 紅色代表凸出紙面，綠色代表凹入紙面 I. Simple Choice ( 3 points each ) 1. What is the IUPAC name for the following compound? ／＼／＼／＼ ∣ ∣ ／＼ ＼ (A) 3-isopropyl-5-ethylheptane (B) 2-methyl-3-ethyl-5-ethylheptane (C) 3,5-diethyl-2-methylheptane (D) 2-methyl-3,5-diethylheptane 2. Which of the following compounds are constitutional isomers? ∣ ∣ ∣ ∣ ＼／＼ ＼／＼ ＼／＼ ＼／＼ ∣ ∣ ∣ ∣ ∣ ／＼／＼／＼／＼ ／＼／＼／＼／＼ ／＼／＼／＼／ ＼／＼／＼／ ∣ ∣ ∣ ∣ ∣ ∣ ∣ ∣ ／＼ A. B. C. D. (A) A and C (B) B and D (C) C and D (D) A and D 3. Which of the following is a wedge and dash projection for the following Newman projection? H Cl H H Cl ＼ ∣ ／ ＼ ∣ ／ ＼ ∣ ／ ＼ ∣ ／ ∣ ╭∣╮ ╭│╮ ╭∣╮ ╭∣╮ ／＼／ │∣│ │││ ∣∣∣ ∣∣∣ ∣ ／┬＼ ／┬＼ ／┬＼ ／┬＼ Cl ↖ ／ │ ＼ ／ ∣ ＼ ／ ∣ ＼ ／ ∣ ＼ Cl H Cl H H (A) (B) (C) (D) 4. Which of the following is the most stable isomer? (A) ∣ (B) ∣ (C) ∣ (D) ∣ ／＼／ ／＼／ ／＼／ ／＼／ ∣ ∣ ∣ ∣ ∣ ∣ ∣ ∣ ＼／ ＼／ ＼／ ＼／ ∣ ∣ ∣ ∣ ／＼ ／＼ ／＼ ／＼ 5. Identify the most acidic proton on the following compound. Hc Ha ／ ∣ ∥ ＼／＼／＼／＼／＼ ∣ Hd Hb (A) Ha (B) Hb (C) Hc (D) Hd 6. The basic species are arranged in decreasing order of basicity in the sequence: (A) F- > -OCH3 > -NH2 > CH3CH2- (B) -OCH3 > CH3CH2- > -NH2 > F- (C) CH3CH2- > -NH2 > -OCH3 > F- (D) -NH2 > CH3CH2- > F- > -OCH3 7. Which of the following reaction does not proceed? (A) CH3Li + CH3CH2OH ─→ CH4 + CH3CH2OLi (B) HC≡CH + NaOH ─→ HC≡CNa + H2O (C) HC≡CNa + H2O ─→ HC≡CH + NaOH (D) CH3OH + NaH ─→ CH3ONa + H2 8. Which of the following molecules, with any formal charges omitted, would be considered the most likely Lewis structure for nitric acid, HNO3? .. .. .. .. Ｏ: :Ｏ Ｏ: .. Ｏ: ∥ .. ..＼..／.. Ｈ :Ｏ: ∥ Ｈ Ｎ＝Ｏ: Ｎ ＼ ∣ Ｈ Ｎ ＼ ／ ∥ Ｎ＝Ｏ ＼ ／ ＼.. :Ｏ Ｏ:　　　　　　　.. ＼.. :Ｏ Ｏ: .. ／.. Ｏ: .. .. Ｈ .. I II III IV (A) I (B) II (C) III (D) IV 9. For a bond forming reaction involving donation of electrons between atoms, electron density is transferred into which molecular orbital of the accepting atom? (A) σ orbital (B) p orbital (C) s orbital (D) LUMO 10. Which of the following statement is CORRECT description for the structure shown below? Cl Cl ＼／＼／ ∣ ∣ ＼／＼／＼ ／＼ ∣ Cl Cl (A) Compound 5,8-bis(1-methylethyl)dodecane has 2 tertiary Hydrogens. (B) Compound 4-(1-ethylpropyl)-2,3,5-trimethylnonane has 5 tertiary Hydrogens. (C) Compound 2,6,6-trimethylbicyclo[3,1,1]hepta-2-ene has 3 secondary Hydrogens. (D) The most stable structure of 2,3,4,6-tetrachloro-1-tert-butylcyclohexane shown below has 4 chlorine atoms at the equatorial positions. 11. Of the following molecules, which is expected to have the highest melting point? ∣ ＼／ ∣ ／＼／ ／＼／＼ ／＼ ／＼ I II III IV (A) I (B) II (C) III (D) IV 12. Which of the following statements best describes the carbon-chlorine bond of the molecule below? .. H :Cl: ＼ ／ H Ｃ　　 H ＼ ／ ＼ ／ Ｃ　　　Ｃ ／＼ ／＼ H H H H (A) nonpolar / no dipole (B) polar / δ+ at carbon and δ- at chlorine (C) polar / δ- at carbon and δ+ at chlorine (D) ionic II. What is the IUPAC name for the following compounds ( 3 points each ) ／＼／＼ ∣ ＼／ 　　 ／ ／ │ ＼ ／＼／＼ ／＼ ∣ ＼ ∣ ／￣￣ \＿/▽ ／＼／＼ ＼／＼／ ∣ ╳＿∕ ／ ＼／ (a) ／ (10個C) (b) (14個C) (c) (14個C) P.S.因為圖有點難畫所以解釋一下，基本上碳都在頂點上 III. Explain the following terms concisely ( 3 points each ): (A) Leveling effect (B) Frontier orbitals (C) Electrophile / Nucleophile (D) Solvation (E) Polarizability IV. What is the energy difference between the staggered and eclipsed conformations of 2,2-dimethylpropane if the eclipsing cost of Me and H is 6 kJ/mol? ( 6 points ) Please note each hydrogen-hydrogen eclipsing interaction in ethane costs about 4.0 kJ/mol. V. Sketch the molecular orbitals for acetylene (10 points ). VI. By viewing from C2-C3 axis, draw Newman projections for the two eclipsed and two staggered conformational isomers of 2-methylbutane. Indicate the one has the highest energy and the one has the lowest energy ( 8 points ). VII. For each of the following resonance hybrids, rank the contributing restructures in order of their relative importance (6 points ). a) .. - :Ｏ: :Ｏ: ∥ .. │ + Ｈ─Ｃ─ＮＨ2 ←──→ Ｈ─Ｃ＝ＮＨ2 b) .. .. - .. + Ｏ: :Ｏ: Ｏ: ∥ + │ - │ Ｈ2Ｃ＝ＣＨ─ＣＨ ←→ Ｈ2Ｃ─ＣＨ＝ＣＨ ←→ ＣＨ2─ＣＨ＝ＣＨ c) + .. - ..- + Ｈ3Ｃ─Ｎ≡Ｃ─Ｏ: ←──→ Ｈ3Ｃ─Ｎ─Ｃ≡Ｏ: .. .. VIII. Supply the curved arrows necessary for the following reactions. ( 6 points ) (A) ..- .. :Ｏ: Ｏ: ∣ .. ∥ -.. Ｈ─Ｃ─Ｏ─Ｈ ──→ Ｈ─Ｃ + :Ｏ─ＣＨ3 │ .. ＼.. .. :Ｏ Ｏ─Ｈ ..＼ .. ＣＨ3 (B) CH3 CH3 ..- │ .. │ ..- H H Ｈ─Ｏ: + Ｈ─ＣＨ2─Ｃ─Cl: ─→ Ｈ2Ｃ＝Ｃ + :Cl: + ＼..／ .. │ .. │ .. Ｏ CH3 CH3 .. IX. Draw the most stable chair conformation of glucose and a chemical structure for 1-cyclopropyl-3-methylcyclopentane, respectively ( 6 points ). OH ／ OH ∣ ＼／＼O ∣ ∣ ／＼／＼ OH ∣ OH OH Glucose --

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