課程名稱︰有機化學 課程性質︰ 課程教師︰方俊民 開課學院：生農 開課系所︰農藝動科昆蟲系 考試日期（年月日）︰April 19,2011 考試時限（分鐘）：120 mins 是否需發放獎勵金：YES （如未明確表示，則不予發放） 試題 : I.Simple choice(42%)There is only one correct answer in each question. 1.Which covalent bond has the highest polarity? (A)C-H (B)N-H (C)O-H (D)Si-H 2.The hybridization at nitrogen atom of HCN is (A)p3 (B)sp (C)cp2 (D)sp3 3.Which molecule has the lowest pKa? (A)HC≡CH (B)H2C=CH2 (C)CH3CH2NH2 (D)CH3CH2OH 4.Which molecule is the strongest Lewis acid?(A)BF3 (B)BCl3 (C)FeCl3 (D)AlCl3 5.Which molecule is a ketone? (A)CH3COCH3 (B)CH3CHO (C)CH3CO2CH3 (D)CH3OCH3 6.Which alkene that has no dipole moment? (A) (Z)-1,2-dichloropropene (B) (E)-1-chloropropene (C) (E)-1,2-dichloroethene (D) (Z)-2,3-dichloro-2-butene 7.Which alkene will release the most heat (ΔH°) on hydrogenation? (A) ethene (B)propene (C)cis-2-butene (D)trans-2-butene 8.Which is the strongest base? (A)OHΘ (B)HSΘ (C)H2NΘ (D)ClΘ 9.Which is the most powerful nucleophile?(A)FΘ (B)ClΘ (C)BrΘ (D)IΘ 10.The C=C bond distance in ethene C2H4 is near (A)0.71A (B)1.21A (C)1.34A (D)1.54A 11.The number of unit of unsaturation(degree of unsaturation) in a molecule C3H4Cl2O2 is(A)1 (B)2 (C)3 (D)4 12.Acetaldehyde CH3CHO can act as a Lewis base, because (A)the molecule contains a methyl group (B)the C-H is a σ bond (C)the oxygen atom has lone pairs of electrons (D)the C=O double bond has π electrons 13.The C-C bond angles in a cyclohexane ring is close to (A)90° (B)109° (C)120° (D)180° 14."Resolution" is a method for (A)separation of constitutional isomers (B)separation of configurational isomers (C)separation of diastereomers (D)separation of enantiomers 15.Butane and cyclobutane are (A) constitutional isomers (B)configurational isomers (C) conformational ismoers (D) not isomers 16.Which is aprotic polar solvent?(A)hexane (B)benzene (C)acetone (D)ethanol 17.Which compound can discharge the brown color of bromine instantly at room temperature? (A) cyclohexane (B) 2-hexyne (C) cyclohexanol (D) 2-chlorohexane 18.For a molecule of carbon monoxide(:C≡O:), (A) this molecule has positive charge (B) this molecule has negative charge (C) the carbon has positive formal charge (D) che carbon has negative formal charge 19.The relationship between cyanate ion ΘO-C≡N and isocyanate ion O=C=NΘ is (A) resonance forms (B) constitution isomers (C) configurational isomers (D) conformational isomers 20.Which compound has the same boiling point as that of (R)-1,2-difluoropropane? (A) 1,1-difluoropropan (B) (S)-1,2-difluoropropane (C) 1,3-difluoropropan (D) 2,2-difluoropropan 21.A sample of compound X(0.4g) is dissolved in ethanol(10 ml) and placed in a tube of 10 cm (1 dm) in length. The observed optical rotation is +4.8, so the specific rotation[α] equals (A) +192 (B) +120 (C) +19.2 (D) +12 II.(6%)The pKa values are shown: NH4+(pKa9),H2O(pKa16),NH3(pKa35). (i)What is the conjugate base of H2O? (ii)What is the conjugate acid of H2O? (iii)Will the reaction of NH4+ and H2O at equilibrium favor the formation of NH3? Why? III.(8%)Octane is a major component in gasoline. The density of octane is 0.7 g/mL. Isooctane is the trivial name of 2,2,4-trimethylpentane, which shows good anti-knock property in combustion (i)Draw the structures of octane and isooctane. (ii)Are they configurational isomers? (iii)Write the equation for oxidation of octane with oxygen to carbon dioxide (CO2) and water. (iv)How many kilograms (kg) of CO2 will be generated by oxidation of 10 liters of octane? IV.(10%)There are four alcohols and three ethers having the molecular formula C4H10O. Two of them are 1-butanol (CH3CH2CH2CHOH) and diethyl ether (CH3CH2OCH2CH3). (i)Show the structures of other three alcohols, and classify them into primary, secondary and tertiary alcohols. (ii)Show the structures of other two ethers, and give their IUPAC names. V.(10%)Structures of 1,3-dimethylcyclohexane (i)Draw the most stable conformation of cis-1,3-dimethylcyclohexane. (ii)Draw the most stable conformation of trans-1,3-dimethylcyclohexane. (iii)Briefly explain the 1,3-diaxial interaction. (iv)Which 1,3-dimethylcyclohexane is a meso compound? (v)Show the structure of (1R,3R)-1,3-dimethylcyclohexane. VI.(4%)The staggered conformer is usually more stable than the eclipsed isomer. (i)Draw the most stable staggered conformer of 1,2-difluoroethane in Newman projection. (ii)However, an eclipsed conformer of 2-fluoroethanol is more stable than the staggered conformers due to intramolecular hydrogen bonding. Draw this eclipsed conformers with intramolecular hydrogen bonding. VII.(6%)A method for the preparation of tert-butyl methyl ether is shown. H3C CH3 ╲ cat. H2SO4 ｜ === CH2 + CH3OH ------------> H3C—— OCH3 ╱ ｜ H3C CH3 (i)Is this addition, elimination or substitution reaction? (ii)The catalytic role of H2SO4 in this reaction is to generate a reactive intermediate?What is the structure of this intermediate? (iii)Show the reaction rate equation. VIII.(6%)The E2 reaction of (2S,3S)-2-bromo-2,3-diphenylbutane with KOH gives a product of (Z)-2,3-diphenyl-2-butene. (i)Draw the structure of (2S,3S)-2-bromo-2,3-diphenylbutane. (ii)Draw the structure of(Z)-2,3-diphenyl-2-butene. (iii)Show the E2 mechanism. IX.(8%)Show the structures or reagents A-H to complete the following reactions. Consider the regio- and srereochemistry in appropriate cases. 1)BH3 H2O,H2SO4 (A,C5H10)------------> ╲____╱ (B,C5H10)-----------> ╲____╱ 2)H2O2,NaOH ╱ ╲ ╱ ╲ OH OH ╱╲ ╱ ╲ ╲====╱ + Br2 ----> (C) ╲╱╲ + (D) ---->╲╱╲ + SO2 + HCl ｜ OH ｜ Cl H ｜ ╱╲╱╲ ----> (E) ╱╲╱\\ OH O ╲ ==== + CH3CO3H -----> (F) +CH3CO2H ╲ ___ 1)O3 ▼ ╱ \\___ ----------> (G) H"""╱╲ O H3O+ ╲___╱ 2)(CH3)2S ╱ ╲▲----->(H) ╲____╱"""H --

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