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： 開課系所︰公衛系、農化系、森林系 考試日期（年月日）︰2010/11/04 考試時限（分鐘）：110 Min 是否需發放獎勵金：是 （如未明確表示，則不予發放） 試題 :(黃色為雙鍵，紅色為三鍵) Ⅰ.Simple Choice(Only one answer is correct﹔3 points each) 1.Which compound is not a constitional isomer of the others? Br Br Br │ ﹨／ ｜ ╲ Br ／＼ ／╲ ╱╲ ∕ ＼／ ｜ ｜ ／ ｜ ｜ ／＼ ∥ ╲／ ／ ／ \╴/ ╲／＼ Br Ⅰ Ⅱ Ⅲ Ⅳ Ⅴ (A) ⅠandⅡ﹔(B) Ⅱ﹔(C) Ⅲ﹔(D) ⅣandⅤ 2. In which of the following does the central atom have 2 pairs of non-bonding electrons? 2- (A) O3；(B)CO2；(C)CO3 ； (D)H2S 3. Listed below are electron dot formulas for several simple molecules and ions. All valence electrons are shown；however,electrical charges have been omitted deliberately Ｈ Ｈ Ｈ Ｈ ‥ ‥ ‥ ‥ H:Be:H H:Be:H H:Ｎ:H H:Ｎ:H H:Ｏ:H 　　　‥ ‥ ‥ ‥ Ｈ Ｈ Ⅰ Ⅱ Ⅲ Ⅳ Ⅴ Which of the structures actually bear(s) a positive charge? (A) Ⅰ; (B) Ⅱ; (C) Ⅳ＆Ⅴ; (D) Ⅲ＆Ⅴ 4. Which of the following species contributes more to the overall hybrid for the species in the box? ╭─────╮ │ Θ／＼│ ／＼Θ ╱╲ ╱╲ ╱╲ │ ／￣\╴/│ ╱￣\╴/ ╱￣\╴/ ╱￣\╴/ ╱￣\╴/ │ N ∕ │ N ∕ N ∕Θ N ∕ N ∕ │ ╲∕ │ ╲∕ ╲∕ Θ╲∕ Θ╲∕ ╰─────╯ Ⅰ Ⅱ Ⅲ Ⅳ (A) Ⅰ; (B) Ⅱ; (C) Ⅲ; (D) Ⅳ 5. Which of the following species contributes more to the overall hybrid for the species in the box? ╭──────╮ ⊕ │ ⊕｜ SCH3│ ｜ SCH3 ｜ SCH3 ｜ SCH3 ｜ SCH3 ｜╲／╲╱ │ ╲／╲╱ ╲╱╲╱ ╲╱╲╱ ╲╱╲╱ ｜ ｜ │ ｜ ⊕ ｜ ｜ ⊕ ｜ ｜╱╲ │ ╱╲ ⊕╱╲ ╱╲ ╱╲ ╰──────╯ Ⅰ Ⅱ Ⅲ Ⅳ (A) Ⅰ; (B) Ⅱ; (C) Ⅲ; (D) Ⅳ 6. When the 1s orbitals of two hydrogen atoms combine to form a hydrogen molecule,how are the electrons distributed in the resulting molecular orbitals? (A) 2 electrons in the bonding molecular orbital (B) 1 electron in the bonding molecular orbital, 1 electron in the non-bonding molecular orbital (C) 1 electron in the bonding molecular orbital, 1 electron in the antibonding molecular orbital (D) 2 electrons in the non-bonding molecular orbital 7. Which is the shortest og the carbon-carbon single bonds indicated by arrows in the following compounds? (A) (B) (C) CH3 (D) ↓ ↓ ↓ ╱ ↓ H3C—CH3 H3C─C≡CH H3C─CH HC≡C—C≡CH 8. Identify the atomic orbital. The lone pair electrons on the N atom are contained in:(O上的雙引號表示lone pair) "O" ╱ ╲ :N H ︳ C ╱ ╲ H3C H (A) 2sp2; (B)2sp3; (C)2sp; (D)2s 9. Of the following common organic solvents which one is predictes to have a smaller dipole moment? (A) Chloroform,CHCl3; (B) Acetone,(CH3)2CO; (C) Dimethylsulfoxide,(CH3)2SO; (D) Acetonitrile,CH3CN 10.What common group is attached to both the ether and 3級 amine in the following molecule? OCH2C6H5 ╱╲╱╲╱ ﹨ ｜ ︱ ﹨ ︱ NBn ￣╲╱ (A) ethyl; (B) phenyl; (C) heptyl; (D) benzyl 11.Which functional group is not contained in prostaglandin E1? O H O ︳▼ ︳ ╱ ╲╱╲╱╲╱╲╱ ╲ ﹨ ｜ ﹨ ｜ HO""￣￣:╲╱╲╱╲╱╲╱ ▲ : HO"" H H ▲ H (A) Ketone; (B) secondary alcohol; (C) tertiary alcohol; (D) carboxylic acid 12.Newman projection of compound A is given below. Which of following is the same compound of A? CH3 (A) (B) (C) Br (D) H3C ∣ H Br Br H ｜ CH3　　　ＣH2CH3 ╲ │ ／ ︳ ／＼／ ＼ ｜ ╱ ＝ ˊ￣│￣ˋ ╱ ╲／ : ˊ￣｜￣ˋ H◤Ｃ◥Br ｜ │ ︱ : ｜ ｜ ｜ ＝ ˋ╱ ╲ˊ ˋ╱ ╲ˊ ＣH3 ╱─┬─╲ ╱─┬─╲ H ∣ H H3C │ H Br Ｈ 13.A split peak for the IR absorption due to bond streching is observed for the carbonyl group in which of these compounds? (A) (B) (C) (D) O O O O O ︳ ︳ ︳ ︳ ︳ CH3C—OH CH3C—OCH2CH3 CH3C—NH2 CH3C—O—CCH3 14.Rank in order of increasing vibration frequency of the following stretchings in the frame ┌─┐ R │Ｏ│ ＣH3 ┌──┐ ＼──┐ │︱│ ┌┼──┐ R┼C≡N│ ｜C─O│ R┼Ｃ┼NH2 R┼Ｎ─H │ └──┘ ╱──┘ └─┘ └───┘ R Ⅰ Ⅱ Ⅲ Ⅳ (A) Ⅰ＞Ⅲ＞Ⅳ＞Ⅱ (B) Ⅳ＞Ⅰ＞Ⅱ＞Ⅲ (C) Ⅱ＞Ⅲ＞Ⅰ＞Ⅳ (D) Ⅲ＞Ⅱ＞Ⅰ＞Ⅳ 15.Which statement is true? (A) Butane and cyclobutane are constitutional isomers. (B) E-1,2-dichloropropene and trans-1,2-dichloropropene are different compounds. (C) Ethane contains numerous congormational isomers including eclipsed and staggered forms. (D) The chair conformational isomer of cis-1,2-dichlorocyclohohexane must display two chlorine atoms at equatorial position. 16.Which of the following are constitutional isomers of 4-isopropyloctane? Ⅰ.3-ethyl-2,4,5-trimethyloctane Ⅱ.Isobutylcyclohexane Ⅲ.4-ethyl-2,3-dimethylheptane Ⅳ.4-ethyl-2-methyloctane (A) Ⅰ,Ⅳ; (B) Ⅱ,Ⅲ; (C) Ⅰ,Ⅱ; (D) Ⅲ,Ⅳ 17.Which statement about orbitals is false? (A) Orbitals are regions of space where electrons are found. (B) Orbitals may contain up to two electrons. (C) Orbitals are filled in order of decreasin energy. (D) Orbitals of equibalent energy are half filled vefore adding two electrons to any one of them. 18.Which is the order of decreasing acid strength of the following coumpounds (greatest first)? O O O O ︳ ︳ ︳ ︳ Cl C Br C F H H C ╲ ╱ ╲ ╲ ╱ ╲ ╲ ╱ ╲ ╲ ╱ ╲ C OH C OH C OH C OH H2 H2 H2 H2 Ⅰ Ⅱ Ⅲ Ⅳ (A) Ⅱ,Ⅰ,Ⅲ,Ⅳ (B) Ⅲ,Ⅳ,Ⅰ,Ⅱ (C) Ⅲ,Ⅰ,Ⅱ,Ⅳ (D) Ⅳ,Ⅱ,Ⅰ,Ⅲ 19.Which of the following are pairs of contributinf resonance structures? "O" CH2 Ⅰ. ╱ ＼ ←───→ ╱ ╲‥ CH3 CH3 CH3 ＯH ‥ ‥ Θ ⊕ Ⅱ. H2C—Ｏ ←───→ H2Ｃ—Ｏ: ‥ Θ Θ Ⅲ. H2C─CH─ＣH2 ←───→ H2Ｃ─CH─CH2 ‥ ‥ Θ ‥ 　　　　　　　　　‥Θ Ⅳ. 　:Ｎ─C─Ｏ ←───→ :N—C—Ｏ： ‥ ‥ ‥ (A) Ⅱ,Ⅳ (B) Ⅰ,Ⅱ,Ⅲ (C) Ⅲ,Ⅳ (D) Ⅱ,Ⅲ,Ⅳ 20.Which acid-base reaction would not take place as written? (A) CH3Li + CH3CH2OH ────→ CH4 + CH3CH2OLi (B) HC─CH + NaOH ────→ HC─CNa + H2O (C) H2C─CH2 + CH3Li ────→ H2C─CHLi + CH4 (D) CH3OH + NaH ────→ CH3ONa + H2 Ⅱ.Five IUPAC names for the following compounds(3 points each) a) OH b) ^ c) ｜ ｜\ ∣ ｜ ｜ ╱╲ ｜^╴╱￣ ╱╲╱╲╱╲╱╲ ｜ ｜ ╱｜╴ ﹨ ｜ ｜ ╱╲╱╲／ ╱￣╲ /╱ ㄟ﹨ ╱╲／ Br ∕＼ ╲╴╱￣ Ⅲ.Write a bond-line formula for each of the following compounds(3 points each) a) Draw the compound X in the most stable chair form CH3 H ▼ ▼ ╱╲╱╲ ｜ ｜ ｜ compound X ╲╱╲╱""OH ▲ ︰ HO Ｈ b) 2-(2-methylpropyl)-spiro[4,5]decane; c) Trans-bicyclo[4.3.0]nonane Ⅳ.Supply the curved arrows necessary fot the following reactions(3 points each a) ‥– ：Ｏ： "O" ｜ ‥ ︳ –‥ H—Ｃ—Ｏ—H ──→ C + ︰Ｏ—CH3 ｜ ‥ ／ ＼‥ ‥ ：Ｏ—CH3 H Ｏ—H ‥ ‥ b) CH3 CH3 ‥– ︳ ‥ ︳ ‥– ‥ H—Ｏ︰ + H—CH2—C—Cl︰ ──→ C + ︰Cl︰ + H—Ｏ—H ‥ ︳ ‥ ╱ ╲ ‥ ‥ CH3 H2C CH3 Ⅴ.Please write three kinds of intermolecular interactions and explain how they can affect physical properties of molecules(9 points). Ⅵ.Please explain the following terms(9 points):A)Frontier Orbitals; B)Leveling effect Ⅶ.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). --

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