Organic Chemistry,Spring 2004-Final Exam B (有机化学期末考试试题B) By Junru wang(E俊周 Life Science college Northwest Sci-Tech University of Agriculture and Forestry NAME_ _STUDENT No. CLASS Honor Pledge:I pledge on my honor that I have neither given nor received aid on this assignment.】 SECTION I-MULTIPLE CHOICE,ETC (2 POINTS EACH) CHO 6.In the box draw the structure of 7.In the box rght,draw trans-1-bromo-2-chlorocyclohex ane using a"chair"structure in its most stable conformation. 第1页共6页
第 1 页 共 6 页 Organic Chemistry, Spring 2004 – Final Exam B （有机化学期末考试试题 B） By Junru wang(王俊儒) Life Science college Northwest Sci-Tech University of Agriculture and Forestry NAME___________ STUDENT No._____________CLASS____________ Honor Pledge: I pledge on my honor that I have neither given nor received aid on this assignment. ____________________________________ SECTION I - MULTIPLE CHOICE, ETC (2 POINTS EACH) In the space provided, give the best IUPAC name(both in Chinese and English) for the compound shown on the right (include E-Z designation if avialable). 1. __________________________________ C H O 2. __________________________________ 3. __________________________________ O H O 4. __________________________________ N O M e C H3 C H3 5. __________________________________ M e M e B r 6. In the box right, draw the structure of 3,3-dichlorobicyclo[3.2.2]nonane. 7. In the box rght, draw trans-1-bromo-2-chlorocyclohex ane using a “chair” structure in its most stable conformation
8.In the box below.draw the structure of cis-3-methyl-cyclopentanecarbaldehyde. 9.Give the configuration of the indicated carbons CH H 10.Examine the pairs of structures below and identify their relationship to one another,using the letter codes below (2 points each): A-the identical structure.B-constitutional isomers.C-conformational isomers.D- diastereomers.E-enantiomers.F-none of the above. B CL CHO CHOH HO-H HO-H H-OH H-OH HO-H CHOH CHO CI HHY H CN 11.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 B人c人E义人 12.Which of the following molecules meets the Huckle definition for aromaticity: 13.An unknown compound gives a copious yellow precipitate when it is reacted with 第2页共6页
第 2 页 共 6 页 8. In the box below, draw the structure of cis-3-methyl-cyclopentanecarbaldehyde. 9. Give the configuration of the indicated carbons . C H O H O H O H C H2 O H O H C H3 H 10. Examine the pairs of structures below and identify their relationship to one another, using the letter codes below (2 points each): A - the identical structure. B - constitutional isomers. C - conformational isomers. D – diastereomers. E – enantiomers. F - none of the above. C l C l ___________ C H3 B r C H3 B r ___________ C H O H O H H O H H O H C H2 O H C H2 O HJ H O H H O H H O H C H O _______________ C H2 C H3 C H3 H H C H2 C H3 H C H3 H ___________ H H CH3 Cl H3C H Cl H CH3 CH3 H H ___________ H C N C l C N C l ___________ 11. 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? O B r B r O O O O O A . B . C . D . E. 12. Which of the following molecules meets the Hückle definition for aromaticity: A. B . C . D. E. 13. An unknown compound gives a copious yellow precipitate when it is reacted with
2.4-dinitrophenylhydrazine reagent:you can say with certainty that the unknown compound: A.is a ketone B.is a ketoneoran aldehyde D.a and c are both correct E.this qualitative test yields ambiguous results:none of the above are correct 14.which is correct in consideration of the main produt of the following reaction? C.No correct product is given 5.Circle(o)the stro one&underline the weakest in each set.(2 points each) a.Nucleophilicity:CHgNH2 CH4 H2O PhCH2S o.Acidity Carbocation Stability Reactivity In SN2 react e.Basicity 第3页共6页
第 3 页 共 6 页 2,4-dinitrophenylhydrazine 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 c are both correct E. this qualitative test yields ambiguous results; none of the above are correct 14. which is correct in consideration of the main produt of the following reaction? O O O O A. O O O O B. O O O O C. No correct product is given 15. Circle(o) the strongest one & underline the weakest in each set. (2 points each) a. Nucleophilicity: CH3NH2 CH4 H2O PhCH2Sb. Acidity C F O H 3 O C H O H O Cl Cl C H O H 2 O F C H O H 3 O C H O H 3 C H2 O c. Carbocation Stability d. Reactivity In SN2 reactions B r C l C l C l e. Basicity
66565 f.Reactivity in SN1 reactions g.Rate of Friedel-Crafts acylation 16.For each of the structures below.the structure on the left is complete and the structure on the right is intended to be exactly the same structure but missing various components.Complete the structures on the right by adding the missing components in the proper locations. CH2CHg H.C CH 17.For the structure below,the structure on the left is not the most stable form of the molecule.On the right,complete the most stable structure of the same molecule. CHa _CH3 H C(CHa)3 CHa 18.Label the following radicals in the order of their decreasing stability(#6 is the most stable,#1 is 第4页共6页
第 4 页 共 6 页 N H C O C H3 N H2 N H2 N H O f. Reactivity in SN1 reactions: C l N ( C H3 ) 3 C l O H C l C l O H g. Rate of Friedel-Crafts acylation O C H3 C H3 O C H3 16. For each of the structures below, the structure on the left is complete and the structure on the right is intended to be exactly the same structure but missing various components. Complete the structures on the right by adding the missing components in the proper locations. a) H3C H Cl Br CH2CH3 Br Cl b) Cl C H2 C H3 H3 C C H3 F Cl 17. For the structure below, the structure on the left is not the most stable form of the molecule. On the right, complete the most stable structure of the same molecule. CH3 H CH3 CH3 C(CH3) H 3 18. Label the following radicals in the order of their decreasing stability (#6 is the most stable, #1 is
the least stable): HN SECTION II REACTIONS AND MECHANISMS(2 points each) 1.NaNHz NHg(Liq) 19. 2.CHaBr HO OH HIO 20.H0 OH B 1.HNO3.H2SO4 Br 2.Fe/HCI 3.NaNOz.HCI.H2O.0C 21. 4.CuCN Na2Cr2O7 22. -CH H,SO4 HaO Heat 1 BHs,THF 2H202.OH H2S04 Heat OH (CHa)2CHCOOH 1.LiALH 1.PBr3 2.H20 2.KCN,DMSO 3.HgO*.heat 1 NaOH SH 2 CHal 26. 1.K2Cr204,H2S04,H20 H OH 2.CHgCH2MgBr,ether 3.H0 27 28.Write a complete mechanism for the substitution (only)reaction shown below. 第5页共6页
第 5 页 共 6 页 the least stable): H2 N H2 N SECTION II REACTIONS AND MECHANISMS(2 points each) 19. 2. CH3Br 1. NaNH2 NH3(Liq) 20. OH HO OH HO HIO4 21. Br Br 1. HNO3, H2SO4 2. Fe/HCl 3. NaNO2, HCl, H2O, 00 C 4. CuCN 22. CH3 Na2Cr2O7 H2SO4 H2O Heat 23. 1 B H 3 , T H F 2 H 2 O 2 , O H - 24. OH H2SO4 Heat 25. (CH3)2CHCOOH 1. LiALH4 2. H2O 1. PBr3 2.KCN, DMSO 3. H3O+ , heat 26. S H 1 N a O H 2 C H 3 I 27. OH H 3. H3O+ 2. CH3CH2MgBr, ether 1. K2Cr2O4, H2SO4, H2O 28. Write a complete mechanism for the substitution (only) reaction shown below
Show all steps and electron pushing arrows.Do not consider any rearrangements X Section III Synthesis(5 points each) 。 29. 第6页共6页
第 6 页 共 6 页 Show all steps and electron pushing arrows. Do not consider any rearrangements. B r I - Section III Synthesis(5 points each) 29. H O 30. O O O O 31. CH3 Br Br NH2 32. HO N=N Br