西北农林科技大学本科课程考试试题 2008一2009学年第二学期ORGANIC CHEMISTRY课程A卷 专业年级：生技基081，生工基0812命题教师：王俊儒审题教师： 考生姓名： 学号： 考试成绩： NOTE:ALL THE ANSWERS SHOULD BE WRITTEN ON THE ANSWER SHEET (注意：所有答案写在答题纸上) Section I-Nomenclature(4 points each,24 points in all)SCORE_ Give the best IUPAC name(both in Chinese and English)for each of the compounds BELOW. OH C-CH.CCH OH COOH 1. 2. CH3 3.Br H -O OH CHO H -Br H OH 6.Br Section II Multiple Choice(1 pointeach,20 points in all)SCORE_ For each of the questions below.circle the letter corresponding to the most correct answer Record the answers to the multiple choice questions on the answer sheet.(2 points each.30 points in all) 7.Which is the highest priority group for the substituents shown below,according to the"E-Zsequence rules: 一C=C-Br A一CHC a e.-CH2OCH3 b 8.Which carboxylic acid is the strongest acid? Br O CH3 O a入 OH b. OH C. OH d. 9.Which of the following is the strongest base? a.CHCH2O b.NH2 c.OH" d.F 第1页共6贝
第 1 页 共 6 页 西北农林科技大学本科课程考试试题 2008—2009 学年第二学期 ORGANIC CHEMISTRY 课程 A 卷 专业年级：生技基 081，生工基 081-2 命题教师：王俊儒 审题教师： 考生姓名： 学 号： 考试成绩： Section I - Nomenclature (4 points each, 24 points in all) SCORE Give the best IUPAC name(both in Chinese and English) for each of the compounds BELOW. 1. H2C CCH2CCH3 CH3 O 2. OH CH3 3. OH Br COOH 4. H OH OH H H H OH OH CH2OH O 5. Cl H CHO H Br CH2CH3 6. CH3 Br Section II Multiple Choice (1 point each, 20 points in all) SCORE For each of the questions below, circle the letter corresponding to the most correct answer. Record the answers to the multiple choice questions on the answer sheet. (2 points each,30 points in all) 7. Which is the highest priority group for the substituents shown below, according to the “E-Z” sequence rules: a. C C Br c. -CH2OCH3 b. d. CHCl3 8. Which carboxylic acid is the strongest acid? OH O OH Br O OH CH3 O OH F O a. b. c. d. 9. Which of the following is the strongest base? a. CH b. c. d. 3CH2O - -NH2 OH - F - NOTE: ALL THE ANSWERS SHOULD BE WRITTEN ON THE ANSWER SHEET （注意：所有答案写在答题纸上）
10.Which of the following species is the most stable cation? a.CHaCHEHa b.C c.CHgCHCHa d.(CH)CH,CH2 11.Which of the following molecules meets the Huckle definition for aromaticity g.00 12.Which is the C2 epimer((差向异构体)ofD-glucose? a.D-(+)-galactose(半乳糖) b.D-(+mannose(甘露糖) c.D-(+-fructose果糖) dD-(--ribose核糖) 13.Which of the following has the highest rate In 4.Which of the w is the quickest towards hydrolysis ir .d.. 15.Which of the molecules below has the highest amount of enol form at e 16.Which of the following would be used for the anti-Markovnikov addition of water toan alkene withou rearrangement a.H2O,H2SO b.Hg(OAc)2,H2O.then NaBH; c.H2SO:then H2O/heat:d.BH:/THF:then H2Oz/NaOH 17.mechanistic pathways respectively,usedin the products nthe following reaction 十1cea -ONO2 Agl a.SN2 b.SNI e.E1 d.E2 18.Foreach of the twenty found inproteins which ofthe following statements regarding their isoelectric point(pl,等电点)is correct? 第2页共6页
第 2 页 共 6 页 10. Which of the following species is the most stable cation? a． CH3CH2CH2 b. CH2 c. CH3CHCH3 d. (CH3 )2CH2CH2 11. Which of the following molecules meets the Hückle definition for aromaticity: a. N b. c. d. O 12. Which is the C2 epimer(差向异构体)of D-glucose？ a. D-(+)-galactose（半乳糖） b. D-(+)-mannose(甘露糖) c. D-(+)-fructose(果糖) d. D-(-)-ribose(核糖) 13. Which of the following molecules has the highest rate In SN2 reactions? 14. Which of the molecules below is the quickest towards hydrolysis in acidic conditions? O O NH O O OH O O O a. b. c. d. O Cl 15. Which of the molecules below has the highest amount of enol form at equilibrium? a. b. c. d. O H O O O H O H O 16. Which of the following would be used for the anti-Markovnikov addition of water to an alkene without rearrangement? a. H2O, H2SO4 ; b. Hg(OAc)2, H2O; then NaBH4; c. H2SO4; then H2O/heat; d. BH3/THF: then H2O2/NaOH 17. Identify the mechanistic pathways, respectively, used in the formation of the products in the following reaction. I AgNO3 C2H5OH ONO2 AgI a. SN2 b. SN1 c. E1 d. E2 18. For each of the twenty amino acids found in proteins, which of the following statements regarding their isoelectric point (pI，等电点) is correct? Br Cl Cl Cl a. b. c. d
a.The isoelectric point is pH at which the net charge on the molecules in solution is0 b.The isoelectric point ispH at which the charge of the alpha-amino groups equals the charge on the alpha-earboxyl groups .The isoelectric point is pHat which the a-carboxyl and a-amino groups are uncharge d.Band Care correct e.A and Bare correct 19.Reaction of an unknown compound with acidic potassium permanganate yields a carboxylic acid and CO:;the unknown compound is a.a tetra-substituted alkene b.adisubstituted alkyne c.a tri-substituted alkene d.a terminal alkene with one alkyl substituent e.a trans,disubstituted alkene 20.Which of the following is true regardingS reactions: a.concurrent El elimination reactions are common b.rearrangement of the carbocation c.the reaction is favored by polar,protic solvents d.a and e only are both correct e.a,b and e are all correct 21.In order for a molecule to be aromatic: a.it must be planar,cyclic and consist of adjacent sp2 atoms containing 4n+2 -electrons b.it must have at least two electrons in each of the degenerate molecular orbitals describing the 元-system c.heteroatoms (must rehybridize so that all unshared pairs of electrons can contribute to the π-system d.a and b only are both true e.a,b and e are all correct 22.The B-sheet conformation ofa protein can be considered an example of. a.Primary structure b.Secondary structure c.Tertiary structure d.Quaternary structure 23.Which of the compounds shown below will react with methyl formate(methyl methanoate)in the presence of methoxide anion(CH)to give a compound,which on treatment with aqueous acid and gentle heating.will decarboxylate to form butanal? a 0、 第3页共6列
第 3 页 共 6 页 a. The isoelectric point is pH at which the net charge on the molecules in solution is 0 b. The isoelectric point is pH at which the charge of the alpha-amino groups equals the charge on the alpha-carboxyl groups c. The isoelectric point is pH at which the α-carboxyl and α-amino groups are uncharged d. B and C are correct e. A and B are correct 19. Reaction of an unknown compound with acidic potassium permanganate yields a carboxylic acid and CO2; the unknown compound is: a. a tetra-substituted alkene b. a disubstituted alkyne c. a tri-substituted alkene d. a terminal alkene with one alkyl substituent e. a trans, disubstituted alkene 20. Which of the following is true regarding SN1 reactions: a. concurrent E1 elimination reactions are common b. rearrangement of the carbocation intermediate is common c. the reaction is favored by polar, protic solvents d. a and c only are both correct e. a, b and c are all correct 21. In order for a molecule to be aromatic: a. it must be planar, cyclic and consist of adjacent sp2 atoms containing 4n+2 -electrons b. it must have at least two electrons in each of the degenerate molecular orbitals describing the -system c. heteroatoms（杂原子）must rehybridize so that all unshared pairs of electrons can contribute to the -system d. a and b only are both true e. a, b and c are all correct 22. The β-sheet conformation of a protein can be considered an example of: a. Primary structure b. Secondary structure c. Tertiary structure d. Quaternary structure 23. Which of the compounds shown below will react with methyl formate (methyl methanoate) in the presence of methoxide anion(CH3O- ) to give a compound, which on treatment with aqueous acid and gentle heating, will decarboxylate to form butanal? a. c. d. b. O O Br Br O O O O e
24.What is the product of the following reaction? 0 H2NNH2,KOH Heat a.3-methylpentane b.3-methyl-2-pentanol c.3-methyl-2-pentene d.3-methyl-1-pentyne 25.What is the product of the following reaction? HgC CH3 Cold,dilute KMnO4. OH a.CH:CH=O b.meso-2,3-butanediol c.racemic(2R.3R)and(2S.3S)-2.3-butanediol .Wht istere 代互变异构) a.resonance forms b.stereoisomers c.constitutional isomers d.different conformations of the same compound Section III Reactions and Synthesis (41 points in all) SCORE. Reactions Draw the major product for each of the following reactions;you should assume that "excess reagents"are present,if appropriate.Show product regiochemistry and stereochemistry where appropriate (for 27-31,2 points each.For 32-36,3points each,25 points). 1.Cl2.FeCl3 →( 2201 0 2.Zn(Hg),HCI OH PCC 28 CH2Cl2 (注：Pyridinium chlorochromate,氯铬酸吡啶盐) ) 29 NH NaBrOO( 31 席4页共6页
第 4 页 共 6 页 24. What is the product of the following reaction? O H2NNH2, KOH Heat a. 3-methylpentane b. 3-methyl-2-pentanol c. 3-methyl-2-pentene d. 3-methyl-1-pentyne 25. What is the product of the following reaction? CH3 H H H3C Cold, dilute KMnO4, OH - a. CH3CH=O b. meso-2,3-butanediol c. racemic (2R,3R) and (2S,3S)-2,3-butanediol d. cis-2,3-epoxybutane 26. What is the relationship between keto and enol tautomers(酮式和醇式互变异构)? a. resonance forms b. stereoisomers c. constitutional isomers d. different conformations of the same compound Section III Reactions and Synthesis（41 points in all） SCORE Reactions Draw the major product for each of the following reactions; you should assume that "excess reagents" are present, if appropriate. Show product regiochemistry and stereochemistry where appropriate (for 27-31,2 points each. For 32-36, 3points each，25 points). 27. 1. Cl2, FeCl3 O O ( ) 2. Zn(Hg), HCl 28 OH PCC CH2Cl2 (注：Pyridinium chlorochromate, 氯铬酸吡啶盐) 29 （ ） OH O HO O 30. O2N CH3 H2O 95 oC KMnO4 31. NaBrO/OHNH ( ) 2 O
2)H0 NO. Fe+HCI 1.NaNOz+HCl.0-5C 2.CuBr 1.NaOEV/EOH 2.CH CH,I )2c COOC2Hs Synthesis(4 points each,16 points in all 第5页共6贝
第 5 页 共 6 页 32 OH O O 1) LiAlH4 2) H3O + 33. O H + NaOH （ ） （ ） H O H 34. 2. CuBr 1. NaNO2+HCl, 0-5 0C Fe+HCl （ ） （ ） NO2 H2N 35. Et OEt O O 1.NaOEt/EtOH 2.CH3CH2 I （ ） （ ） 2.CH3 I 1.NaOEt/EtOH 36. + COOC2H5 H5C2OOC Synthesis(4 points each, 16 points in all.) 37. OC2H5 O O O 38. NH2 Br 39. COOH 40. OH O O
SECTION IV MECHANISMS SCORE_ (5 points each,15 points in all) 41.Write a complete mechanism for the following reaction. 人+，、 火 42.Write a complete mechanism for the following reaction. CHaCH2OH 43.Provide a mechanism for the following reactions Show the movement ofelectrons with the appropriate arrows and indicate equilibrium arrows where relevant. 第6页共6页
第 6 页 共 6 页 SECTION IV MECHANISMS SCORE (5 points each, 15 points in all) 41. Write a complete mechanism for the following reaction. Br2 Hv Br 42. Write a complete mechanism for the following reaction. O Cl + CH3CH2OH O OCH2CH3 + HCl 43. Provide a mechanism for the following reactions. Show the movement of electrons with the appropriate arrows and indicate equilibrium arrows where relevant. O O Br FeBr3 Br2