課程名稱︰有機化學一 課程性質︰化學系必修 課程教師︰楊吉水 開課學院：理學院 開課系所︰化學系 考試日期（年月日）︰97.10.23 考試時限（分鐘）：110，之後延長5分鐘 (10:20~12:10→12:15) 是否需發放獎勵金：是 （如未明確表示，則不予發放） 註：試題中所有圖片以[PicXX]表示者， 　　請自 http://0rz.tw/9b52C 下載圖片。（下載按鈕在網頁左下角） 試題： A.單一選擇題（每題三分，選十題作答，共三十分） 1.For a reversible reaction with ΔG°= 2.72 kcal/mol, what is the most possible value for the equilibrium constant K at 297K? (a) 0.1 (b) 0.01 (c) 0.001 (d) 10 (e) 100 2.Regarding the relative boiling points in each pair of compounds, which of the following statements is TRUE? (a) CH3CH2COOCH3 is higher than CH3CH2COOH because of larger molecular weight. (b) Diethyl ether is higher than 1-butanol because of dipole-dipole interactions. (c) Tetrahydropyran [Pic01] is lower than cyclopentanol [Pic02] because of hydrogen-bond interactions. (d) Acetone (CH3COCH3) is higher than CH3OH because of larger London forces. (e) Isobutane is higher than n-butane because of branching structure. 3.Which of the following is NOT a resonance structure of the others? (a) [Pic03] (b) [Pic04] (c) [Pic05] (d) [Pic06] (e) [Pic07] 4.Which of the following statements is NOT true in terms of the free-radical halogenation reactions of alkanes? (a) Bromination has a better regioselectivity than chlorination (b) Fluorine is more reactive than iodine. (c) The reaction mechanism is a chain reaction. (d) The initiation step is always endothermic. (e) Brominations are faster than chlorinations. 5.The compound [Pic08] has a formal charge of (a) -1 on N (b) +2 on N (c)-1 on Al (d) +1 on Al (e) -1 on Br 6.Which of the following classification for the five species shown below is the most appropriate? 1. H3O+ 2. HBr 3. Cl- 4. AlCl3 5. HO- (a) 1,2,4 are electrophile when 3,5 are nucleophile. (b) 1,2 are electrophile when 3,4,5 are nucleophile. (c) 1,3,4 are electrophile when 2,5 are nucleophile. (d) 1,4 are electrophile when 2,3,5 are nucleophile. (e) 3,5 are electrophile when 1,2,4 are nucleophile. 7.How many of the following pairs of structures are depicting the same compound? 1. [Pic09] and [Pic10] 2. [Pic11] and [Pic12] 3. [Pic13] and [Pic14] 4. [Pic15] and [Pic16] 5. [Pic17] and [Pic18] (a) 1 (b) 2 (c) 3 (d) 4 (e) 5 8.[Pic19] The sum of all the digits that appear in the IUPAC name for this compound is (a) five (b) six (c) seven (d) eight (e) nine 9.Which of the following statements is LEAST likely to be true? (a) The rotation barrier of ethane is 3.0 kcal/mol. (b) The pKa of ethane is 30. (c) The gauche butane interaction is 0.9 kcal/mol. (d) The compound 2-methylbutane has twice as many secondary H's as tertiary H's. (e) In the chlorination of alkanes, 2-methylpropane will react faster than butane. 10.Shown below are five comparisons of acid strengths. Which one of the comparisons is INCORRECT? (a) [Pic20] is more acidic than [Pic21] (b) [Pic22] is more acidic than [Pic23] (c) [Pic24] is more acidic than [Pic25] (d) [Pic26] is more acidic than [Pic27] (e) [Pic28] is more acidic than [Pic29] 11.There are four different substituents, (1)-CN, (2)-CH=CH2, (3)-CH2NH2, (4)CH2Br on an asymmetric carbon. Which choice is the correct priority for determining the R/S configuration? (a) (4)>(1)>(3)>(2) (b) (1)>(2)>(3)>(4) (c) (1)>(2)>(4)>(3) (d) (4)>(2)>(1)>(3) (e) (2)>(3)>(1)>(4) 12.How many of the following compounds would be CHIRAL? 1. [Pic30] 2. [Pic31] 3. [Pic32] 4. [Pic33] 5. [Pic34] 6. [Pic35] (a) 2 (b) 3 (c) 4 (d) 5 (e) 6 B.簡答題　（每大題十分，選七大題作答，共七十分） The following table contains information you might need for answering the questions in this section: Table 1 Bond Dissociation Energy (kcal/mol) ────────────────── CH3-CH3 88 C-H 1° 98 C-H 2° 95 C-H 3° 91 Sn-H 73 C-Cl 79 H-Cl 103 Cl-Cl 58 1.One chair conformation of cis-1-tert-butyl-2-methylcyclohexane is significantly more stable than the other. (a) Draw the two chair conformations of all the H atoms and substituents of this molecule and (b) circle the most stable form. 2.Give an IUPAC name for Each of the following compounds. (a,b: 2%; c,d: 3%) (a) [Pic36] (b) [Pic37] (c) [Pic38] (d) [Pic39] 3.(a) On the basis of Table 1, calculate the ΔG° value for the following reaction at 25℃ with the assumption of ΔS° = 0 kcal/mol‧K and (b) draw a reasonable mechanism for it. [Pic40] 4.Considering the following radical H abstraction reactions, (I) [Pic41] (II) [Pic42] draw a reaction-energy diagram, on the basis of Table 1, for both reactions (I) and (II), which shows (a) their relative changes in activation energy and enthalpy and (b) their relative positions of transition state that conforms to the Hammond postulate. (c) Draw a reasonable structure for the transition state of reaction (I). 5.For 2,3-dimethylbutane, show the conformations in 60° increments associated with their correct relative energies on the diagram below. The Newman projections have been started for you [Pic43]. To complete each conformation, draw in the remaining substituents on carbon 3 (C3) at the back of each Newman projection. Rotate the C3 substituents CLOCKWISE relative to the stationary C2 carbon. [Pic44] [Pic45] 6.(a) Formaldehyde ([Pic46]) has a fairly large dipole moment of 2.33D, but carbon monoxide (CO) has a small dipole moment of 0.11D. Use resonance and electronegativity arguments to explain these results. (6%) (b) Explain why the following equilibrium lies to the right:(4%) [Pic47] 7.Consider the following structures A to D. Identify the following pairs of molecules as enantiomers, diastereomers, or the same compound? (a) A and B (b) A and C (c) A and D (d) B and C (E) B and D (A) [Pic48] (B) [Pic49] (C) [Pic50] (D) [Pic51] 8.Cyclotheonamide A (see the structure below), isolated from marine sponges, is a potent inhibitor of thrombin which plays a role in the clotting of blood. (a) CIRCLE ALL THE STEREOCENTERS and (b) ASSIGN THE R/S CONFIGURATIONS for those needed. (c) How many major types of functional groups are present in this molecule? [Pic52] 9.The guanidine functional group, part of the amino acid arginine and a key functional group found in many proteins, is highly basic due to resonance stabilization of its conjugate acid. Draw (a) the conjugate acid of guanidine and (b) the resonance structures that show how the positive charge is delocalized (Use curved arrows to indicate the flow of electrons.) (6%) [Pic53] (c) Convert the following structures to Fischer projection images. (4%) [Pic54] [Pic55] Over. Good Luck! --

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