课程名称︰有机化学 课程性质︰必修 课程教师︰杨吉水 开课学院：医学院/生农院 开课系所︰医技系/园艺系 考试日期（年月日）︰2011/5/12 考试时限（分钟）：100分钟 是否需发放奖励金：是 （如未明确表示，则不予发放） 试题 : 注：所有的图都在这里 http://tinyurl.com/4xl94fh http://tinyurl.com/3k66d4z http://tinyurl.com/43noau8 http://tinyurl.com/4xub6wj http://tinyurl.com/3tj3bfm http://tinyurl.com/3zyxzak (1) MULTIPLE CHOICE 1. The numbers on the carbon center of the following molecule represent atomic numbers. The molecule is in a. the R configuration b. the S configuration c. The carbon is not a chiral center in this molecule d. The exact configuration cannot be determined without knowing additional atomic numbers. [FIG 1] 2. Which of the following is the definition of a pair of enantiomers? a. A pair of structures that are superimposable mirror images of one another b. A pair of stereoisomers that are non-superimposable mirror images of one another c. A pair of stereoisomers that are not mirror images of one another d. A pair of stereoisomers that have equal specific rotations 3. Which of the following is the denifition of a meso compound? a. A molecule with chirality center which is chiral b. A molecure with chirality center which is not chical c. A diastereomer with no chirality centers d. A chiral compound with more than one chirality center 4. Which of the followong structure represent the same stereoisomer? [FIG 2] a. only 1 and 2 b. only 1 and 3 c. only 2 and 3 d. 1, 2 and 3 5. How mant stereoisomers of 2,3-dimethylbutane exist? a. 1 b. 2 c. 3 d. 4 6. How many stereoisomers of 3-bromo-2-butanol exist? a. 1 b. 2 c. 3 d. 4 7. What is the relationship between the following pair of structure? [FIG 7] a. They are enantiomers b. They are diastereomers c. They are constitutional isomers d. They are identical [FIG 8 & 9] 8. Compound B is the: a. SN2 product b. SN1 product c. E2 product d. E1 product 9. Compond C is the: a. SN2 product b. SN1 product c. E2 product d. E1 product 10. [FIG 10] The mechanism of this reaction is: a. SN1 b. SN2 c. E1 d. E2 11. Which mechanism is favored by the reaction of a tertiary alkyl chloride with ethanol? a. SN1 b. SN2 c. E1 d. E1CB e. E2 12. [FIG 12] What is the IUPAC name of the following compound? a. (R)-1-chloro-3-methyl-2-cyclohexene b. (S)-1-chloro-3-methyl-2-cyclohexene c. (R)-3-chloro-1-methylcyclohexene d. (S)-3-chloro-1-methylcyclohexene 13. [FIG 13] Which of the following would not react with either Na2Cr2O7 or periodinane? a. 1 b. 3 c. 2&4 d. 1&2&3&4 14. [FIG 14] What is the IUPAC name of the following compound? a. cis-4-methylcyclohexanol b. trans-4-methylcyclohexanol c. cis-4-hydroxy-1-methylcyclohexane d. trans-4-hydroxy-1-methylcyclohexane 15. [FIG 15] What is the IUPAC name of the following compound? a. ethyl isopropyl thiol b. 2-methylsulfanylpropane c. ethyl isopropyl disulphide d. ethyl isopropyl sulfide 16. Many nucleophilic addition reactions of aldehydes and ketones are catalysed by acid or base. Bases catalyze hydration by: a. making the carbonyl group more electrophilic b. shifting the equilibrium of the reaction c. making the carbonyl group less electriphilic d. converting the water to hydroxide ion, a much better nucleophile 17. Which of the following is the correct order of decresing acid strength? a. FCH2COOH > CH3COOH > F2CHCOOH b. FCH2COOH > CH3COOH > CH3OH c. CH3CH2OH > ClCH2COOH > BrCH2COOH d. CH3COOH > ClCH2COOH > CH3OH 18. Which of the following would represent the correct reaction conditions for the following conversion? [FIG 18] a. 1.) KMnO4, 2.) LiAlH4 b. 1.) Mg, ether, 2.) CO2, 3.) LiAlH4 c. 1.) NaOH, H2O, 2.) LiAlH4 d. 1.) SOCl2, benzene, 2.) LiAlH4 e. either b or c 19. Which of the following has the highest boiling point? a. butanoic acid b. butan-2-ol c. hexanoic acid d. heptan-3-one 20. What is the major product obtained from the following reaction? [FIG 20] 21. Which of the following compounds is a secondary amide? [FIG 21] 22. What is the IUPAC name of the following compound? [FIG 22] a. 5,5-dimethyl-5-phynulpentanoic acid b. 5-methyl-5-phenylhexanoic acid c. 2,2-dimethylphrnylpropanoic acid d. 5,5-dimethyl-5-phenylbutanal 23. What is the IUPAC name of the following compound? [FIG 23] a. dimethylamino 3-phenylpropanoic acid b. N,N-dimethyl 2-phenylethyl amide c. N,N-dimethyl 3-phenylpropanamide d. dimethyl 2-phenylpropanolamine 24. Which of the following is the correct order of decreasing reactivity in hydrolysis reactions? a. anhydrides > amides > acid chlorides b. amides > acid chlorides > anhydrides c. anhydrides > acid chrorides > amides d. acid chlorides > anhydrides > amides 25. What is the major organic prodct produced by the following reaction? [FIG 25] 26. Which of the following correctly describes a molecule that is achiral? a. Non-superimposability of the molecule on its mirror image b. superimposability of the molecule on its mirror image c. contains a carbon atom with four different sibstituents d. does not have a plane of symmetry e. both b and d 27. Which of the following statement is true regarding pairs of enantiomers? a. They have identical melting points b. They have identical boiling points c. They rotate plane-polarized light in opposite directions d. They produce different products in reactions with chiral reagents. e. all of the above 28. Which of the following statements about an SN2 reaction is true? a. the reaction occurs in 2 steps b. rate = k[RX] c. stabilization of R+ is important d. the reaction causes racemization e. the reaction is favored by aprotic solvents 29. Which conditions favor an efficient (fast, high yield) SN2 reaction btwn an appropriate alkyl halide and a nucleophilic with a charge? a. high concentration of a strong nucleophile, polar protic solvent b. high concentration of a weak nucleophile, nonpolar solvent c. low concentration of a strong nucleophile, polar aprotic solvent d. low concentration of a weak nucleophile, nonpolar solvent e. high concentrarion of a strong nucleophile, polar aprotic solvent 30. What is the rate law for the E2 reaction of an RX with NaOEt in EtOH? a. rate = k[RX] b. rate = k[RX]2 c. rate = k[RX][Na+] d. rate = k[RX][OEt-] e. rate = k[OEt-] 31. The reaction mechanism in the following reaction is [FIG 31] a. an E1 process b. an SN1 process c. an E2 process d. an SN2 process 32. What is the major organic product obtained from the following reaction? [FIG 32] 33. What is the IUPAC name of the following compound? [FIG 33] a. 3-methyl-3-phenylpropanol b. 3-phenylbutanal c. 3-phenyl-1-butanone e. 3-phynylbutanoic acid 34. What is the IUPAC name of the major organic compound abtained from the following reaction? [FIG 34] a. 2,3-dimethylheptan-3-ol b. 2,4-dimethylheptan-4-ol c. 3,5-dimethylheptan-4-ol d. 3,5-dimethylheptan-3-ol 35. Of the following, which represent a possible direct convertion of the reactant to product shown? a. ester to acid chloride b. thioester to acid anhydride c. ester to amide d. acid anhydride to acid chloride (2) Essay Question 1. Assign R or S configuration to each chirality center in the following biological molecules: [FIG E1] 2. Predict the major product of the following reaction: (a) & (c) [FIG E2] (b) CH3CH2CH2CH2OH ---SOCl2---> ? (d) CH3CH2CH(Br)CH3 ---Mg, Ether---> A --H2O--> B 3. Predict the products of the following transformations [FIG E3] 4. Rank the following substances in order of increasing acidity: Acetone (pka 19) Pentane-2,4-dione (pka 9) Phenol (pka 9.9) Acetic acid (pka 4.7) 5. Identify the reagents in the following scheme: [FIG E5] 6. When glucose is treated with NaBH4, reaction occurs to yield sorbitol, a commonly used additive. Show how this reduction occurs. [FIG E6] 7. The following reactivity order has been found for the saponification of alkyl acetates by aqueous NaOH: [FIG E7] 8. Draw the reaction mechanism for the following conversion from enol to keto form: (you should show the resonance structures for the intermediate and use curved arrows) [FIG E8] --

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