西北农林科技大学本科课程考试试题 2012一2013学年第2学期《有机化学》（双语）课程A卷 专业年级：生技基、生工基地12级等7个班命题教师：陶虎.王俊儒，汤江江审题教师： 考生姓名： 学号： 考试成绩： DIRECTIONS-Please answers all questions on the answer sheet provided as completely and clearly as possible.Show all your work for the writing portions of the exam. Part I-NOMENCLATURE (3 points each,24 points in all) SCORE Give the correet IUPAC name (BOTH IN CHINESE AND ENGLISH)or molecular structure for each .(Note the if there H、 HO-H HO-H Oi 6. (R)-2-fluorobutan-1-amine (E)-4-oxobut-2-enoic acid potassium 3-chloropentanoate 第1页
第 1 页 西北农林科技大学本科课程考试试题 2012—2013 学年第 2 学期《有机化学》（双语）课程 A 卷 专业年级：生技基、生工基地 12 级等 7 个班 命题教师：陶虎，王俊儒，汤江江 审题教师： 考生姓名： 学 号： 考试成绩： DIRECTIONS- Please answers all questions on the answer sheet provided as completely and clearly as possible. Show all your work for the writing portions of the exam. Part I - NOMENCLATURE (3 points each, 24 points in all) SCORE Give the correct IUPAC name (BOTH IN CHINESE AND ENGLISH) or molecular structure for each of the compounds BELOW. (Note the configuration if there any). 1. 2. 3. C CH3 C2H5 H C C H CH3 H 4. 5. 6. (R)-2-fluorobutan-1-amine 7. (E)-4-oxobut-2-enoic acid 8. potassium 3-chloropentanoate
Part II-MULTIPLE CHOICE (2 point each,40 points in all) SCORE For each of the questions below,circle the letter corresponding to the most correct answer(s) 9.Predict the reasonable resonance structure for the structure shown below: o是 ao八se八a:0g0 e)none of these 10.Predict the major product of this reaction sequence shown below 285o C 空0g“C 11.What is the expected product(s)for the reaction shown? OH KMnD.HsO42 e)none of these answer 12.Which carboxylic acid is the strongest acid? 13.Which would be the major organic product of this reaction? 2.HNO SO 6 第2页
第 2 页 Part II -MULTIPLE CHOICE (2 point each, 40 points in all) SCORE For each of the questions below, circle the letter corresponding to the most correct answer(s) 9. Predict the reasonable resonance structure for the structure shown below: a) b) c) d) e) none of these CH2 CH O CH2 CH O CH2 CH O CH2 CH O CH2 CH O 10. Predict the major product of this reaction sequence shown below. H 1. BD3 , THF 2. H2O2, NaOH a). H CH3 D OH D CH3 H OH b). OH H H OH c). OH d). D H CH3 e). none of these answers CH3 11. What is the expected product(s) for the reaction shown? (a) (b) (c) d) e) none of these answers O OH O H O O OH KMnO4 , H2SO4(aq) 12. Which carboxylic acid is the strongest acid? OH O OH Br O OH CH3 O OH F O a. b. c. d. 13. Which would be the major organic product of this reaction? 1. Cl2 , AlCl3 2. HNO3 , H2SO4 (a) Cl NH2 (b) Cl NO2 (c) Cl NH2 (d) Cl NO2 (e) none of these answers
14.Predict the major product from the reaction shown. 15.Which of the following is optically active? (a) (b) Br Br CI (e)none of these answers H IH 16.What is the relationship between these two structures? H Br Ph H (a)constitutional (b)conformational (c)diastereomers(d)enantiomers(e)identical 17.Which one of the following group s not a strong nucleophile? a)-CN b)-Br c)-OH d)-I e)CHsOH 18.For each of the twenty minoac found in proteins,which of the follwing statements regarding their isoelectric point(pl,等电点)is correct? A.The isoelectric point is pH at which the net charge on the molecules in solution is1 B.The isoelectric points of acidic amino acids are above pH7.0. C.The isoelectric point is pH at which pH at which amino acids exist as the zwitterion. D.The isoelectric points of neutral amino acids are pH7.0. 19.How many(max.no.)of possible stereoisomers (enantiomers+diasteromers)are there of the molecule shown below (hint:determine the no.of chiral carbons and usea formula discussed in class)? a)1b)2)8d5e)4 20.An unknown compound gives a copious()yellow precipitate when it is reacted with 2,4 dinitrophenylhydrazine(2.4-二硝基苯肼)reagent;,you can say with certainty that the unknown compound: 第3页
第 3 页 14. Predict the major product from the reaction shown. O OH SOCl2 a). O OH Cl b) O Cl c). Cl O OH d). O Cl e). none of these answers 15. Which of the following is optically active? Br Cl I H H (a) (b) F Br (c) (d) I H H H Cl Br (e) none of these answers F Br F Br F F Br 16. What is the relationship between these two structures? Ph Br Cl H H Ph H H Br Cl (a) constitutional (b) conformational (c) diastereomers (d) enantiomers (e) identical 17. Which one of the following groups is not a strong nucleophile? a) –CN b) -Br c) –OH d) –I e) CH3OH 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? A. The isoelectric point is pH at which the net charge on the molecules in solution is 1 B. The isoelectric points of acidic amino acids are above pH 7.0. C. The isoelectric point is pH at which pH at which amino acids exist as the zwitterion. D. The isoelectric points of neutral amino acids are pH 7.0. 19. How many (max. no.) of possible stereoisomers (enantiomers + diasteromers) are there of the molecule shown below (hint: determine the no. of chiral carbons and use a formula discussed in class)? Br F CH3 a) 1 b) 2 c) 8 d) 5 e) 4 20. An unknown compound gives a copious( 很 多 的 ) yellow precipitate when it is reacted with 2,4-dinitrophenylhydrazine (2.4－二硝基苯肼) reagent; you can say with certainty that the unknown compound:
A.is a ketone B.is a ketone or an aldehyde C.is a methyl ketone D.a and care both correct E.this qualitative test yields ambiguous results;none of the above are correct 21.Which of the following reactions will not yield benzoic acid as the major product? CaN Hior 0四 22.Which of the following reagent(s)used for alkylation process of benzene? A.CHCI/AICI B.CH3MgBr/ether/H.O C.MnO/H:O/heat D.NBS/CCI 23.Which of the molecules below has the highest amount of enol form at equilibrium? 0 b、 入H 24.What is the product of the following reaction? 、HNNH,KOH A.2-methylpentane B.3-methyl-2-pentanol C.3-methyl-2-pentene D.3-methyl-1-pentyne 25.Which of the following molecules meets the Huckle definition for aromaticity: A□ a c.△ D.△ 26.Which of the following hemiacetal Carbohydrates is a-D-configuration: CHOH H CH.OH OH OH OH CHOH CH.OH 27.Which would be the major organic product of this reaction? 第4页
第 4 页 A. is a ketone B. is a ketone or an aldehyde C. is a methyl ketone D. a and c are both correct E. this qualitative test yields ambiguous results; none of the above are correct 21. Which of the following reactions will not yield benzoic acid as the major product? 22. Which of the following reagent(s) used for alkylation process of benzene? A. CH3Cl/AlCl3 B. CH3MgBr/ether/H2O C. MnO4 – /H2O/heat D. NBS/CCl4 23. 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 24. What is the product of the following reaction? O H2NNH2 , KOH Heat A. 2-methylpentane B. 3-methyl-2-pentanol C. 3-methyl-2-pentene D. 3-methyl-1-pentyne 25. Which of the following molecules meets the Hückle definition for aromaticity: A. B. C. D. + 26. Which of the following hemiacetal Carbohydrates is a-D-configuration: A. B. C. D. O CH2OH O OH OH OH H O CH2OH O OH OH OH H O OH CH2OH OH OH HO O CH2OH O OH OH H OH 27. Which would be the major organic product of this reaction?
-OH 1.K2Cr2O-/H* 3.CH5C0H (e)none pf these answers Which would be the major organic product of this reaction? NBS.hea OH (e)none of these answers Part III-REACTIONS and SYNTHESIS (2 points for 29-35,3 poiuts for 36-39,26 points) SCORE_ OH PCC 9 CH2Cl2 人 30. 2)H,0 KMnO H2095℃ CI 1.Mg.diethy ether 3.H,0 第5页
第 5 页 OH 1. K2Cr2O7 /H+ 2. SOCl2 3. CH3CH2OH (a) O OCH2CH3 (b) O Cl (c) CH3CH2Cl (d) O OH (e) none pf these answers 28. Which would be the major organic product of this reaction? 1. NBS, heat 2. Li 3. O H H 4. H+ (a) OH (b) Br (c) OH (d) Br (e) none of these answers Part III- REACTIONS and SYNTHESIS (2 points for 29-35, 3 points for 36-39, 26 points) SCORE 29. OH PCC CH2Cl2 30. AlCl3 Cl 31. H O 1）LiAlH4 2）H3O + 32. O2N CH3 H2O 95 oC KMnO4 33. 2. CO2 1. Mg, diethyl ether Cl 3. H3O+
4.CuCN (CHa)2CHCOOH 1.PB3 2.H0 2.KCN,DMSO 35 3.HgO".heat H'C=N' LiAlH.THF H20 .D-coon soc ）LiA 第6页
第 6 页 34. Br Br 1. HNO3 , H2SO4 2. Fe/HCl 3. NaNO2 , HCl, H2O, 00C 4. CuCN 35. (CH3 )2CHCOOH 1. LiALH4 2. H2O 1. PBr3 2.KCN, DMSO 3. H3O + , heat 36. O H + C NLiAlH4 , THF H2O 37. COOH SOCl2（ ） （ ） CH3NH2 （ ） LiAlH4 38. 39
Part IV-MECHANISMS (5 points for each,10 POINTS) 40.Provide a detailed stepwise mechanism for the reaction shown below.Please show all your work indudingelsectonfiow △ 41.Write a complete mechanism for the base-catalyzed crossed aldol reaction shown below.Show all steps and all resonance forms for any intermediates involved. ,义C 第7页
第 7 页 Part IV –MECHANISMS (5 points for each, 10 POINTS) 40. Provide a detailed stepwise mechanism for the reaction shown below. Please show all your work including electron flow. Cl2, FeCl3 NO2 NO2 Cl 41. Write a complete mechanism for the base-catalyzed crossed aldol reaction shown below. Show all steps and all resonance forms for any intermediates involved