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CHEM212FINAL3 - LAST NAME FIRST NAME STUDENT NUMBER FACULTY...

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Unformatted text preview: LAST NAME FIRST NAME STUDENT NUMBER FACULTY OF SCIENCE DEPARTMENT OF CHEMISTRY FINAL EXAMINATION- Version | CHEMISTRY 212 [ll] EXAMINER: Prof. H. Sleiman Friday, December 8, 2006 Associate Examiner: Prof. B. Amdtsen 9:00 am -12:00 pm INSTRUCTIONS: 1. Fill in your name and student number on the answer sheet provided. Be sure to fill the “check bit” as well (first two letters of your last name). Indicate your version number on your card. 2. Put your name on the first page of the exam as well as the second, and hand it in along with the exam sheet at the end of the exam. The exam will not be graded unless there is an answer sheet and an exam for each student. 3. Answer all 40 multiple choice questions in part I on the red answer sheet (80 marks out of 125). Answer all part II questions (45 marks out of 125) on the question sheet. 4. This exam comprises 23 pages (excluding the first page) 5. Molecular models and calculators are permitted. Your molecular model boxes should have nothing but the models themselves. Your invigilators will check them. 6. A periodic table is on the back of your exam sheet. 7. Please do not ask guestions to the invigilators about interpretation of the exam Questions. If you have a query of significance, please summarize it on the front of the exam and it will be evaluated. 8. Corrected exams will not be returned. 9. The Examination Security Monitor Program detects pairs of students with unusually similar answer patterns on multiple choice exams. Data generated by this program can be used as admissible evidence, either to initiate, or corroborate an investigation or a charge of cheating under Section 16 of the Code of Student Conduct and Disciplinary Procedures. F Name: Date: 1. Cyclopentadiene is unusually acidic for a hydrocarbon. An explanation for this is the following statement. A) The carbon atoms of cyclopentadiene are all sp2-hybridized. B) Cyclopentadiene is aromatic. ‘ C) Removal of a proton from cyclopentadiene yields an aromatic anion. D) Removal of a hydrogen atom from cyclopentadiene yields a highly stable free radical. E) Removal of a hydride ion from cyclopentadiene produces an aromatic cation. 2. 2-Bromo-4-nitroaniline is: Br Br [:Mr’ N02 NH? l H! r402 ll Er r”) L. B: .0211 03115 IV V A) 1 B) 11 C) 111 D) IV E) V 3. Free radical chlorination will produce but one monochloro derivative in the case of: A) Propane. B) Butane. C) Isobutane. D) Isopentane. E) Neopentane. Page 1 O 4. What is the structure of the compound L that yields 2 mol of formaldehyde, HIlH’ and O O 1 mol of II " upon ozonolysis followed by treatment with zinc in acetic acid? CH3CCHZCH O O O 1:: 03 || || H g —> 2HCH + CH3 CCHE CH 2) Zn, HOAC I II III O 2% V 1v v A) I B) II C) 111 D) IV E) V 5 . What is the major product of the reaction: CH3 l (j 1) BHasTHF , CH3 {T‘Ha CH3 HCHa 35% mm mm + + enan’riomer- shun-Homer- I II III I'v' A) 1 B) H . C) m D) IV E) Both 111 and IV Page 2 6. Which of these compounds belongs to the class of substances commonly known as "halohydrins"? A) BrCHzCHzCl O B) H ClCHgCOH C) ICH2CH20H D) FCHzCHzNHz HOCHZC=O E) | Cl 7. The major product(s), B, of the following reaction, COQH HNo3 B Hfi04a €02H $02H cozH COZH H,Noz I / COZH COZH ogu cozH N02 I II III would be: A) I B) II C) 111 D) Equal amounts of I and II E) Equal amounts of I, 11 and III 8. Which ion is the strongest nucleophile in aqueous solution? A) F' B) Cl' C) Br' D) I' E) All of these are equally strong. Page 3 9. Select the structure of the conjugated diene. I II III "N‘ | | ‘x A IV v A)I B)II C)]]1 D)IV E)V \ H CGCH5 II o 0 ll _ com; 0 » ‘ rm I: H | o and RISES-£00345 “a”? CIHé 02 V E Ii f» . II If - o and CH2=CH—COCH3 CHf=CH—C{JCH5 and 0 | “a, EIE IV A) I B) 11 C) 111 i D) IV E) None of these Page 4 11. Which of the compounds listed below would you expect to give the greatest amount of meta-product when subjected to ring bromination? OH [:§%33H Ki%;; 1: III 061-13 CH3 w v A) I B) II C) 111 D) IV E) V CH3, 0 HN-fl3 > o .. F5594 ‘00:” CH5 CH3 C“; (j Q E N02 BUSH c0214 CDZH coal-I i H I" A) I B) 11 C) III I D) I and II in roughly equal amounts E) I and III in roughly equal amounts Page 5 13. The product, C, that would result from the following series of reactions, CI H—bmmo- + 6 Alma A mccinimidg alcoholic KOH, hefl'l' peroxides B C B"—@:@B" m Q34) \—f’<j x—/ IV V would be: A) I B) H C) III D) IV E) V 14. The molecules below are: cu3 til-I5 H = r r ; H ”A; CH3 CH3 ; F F E A) constitutional isomers. B) enantiomers. C) diastereomers. D) identical. E) None of these Page 6 15. Which alkene would you expect to be the major product of the following dehydration? OH I'IESOg/heol > 7 {-142 U} 16. Which of the following compounds would be most reactive toward electrophilic substitution? 0H Br II II! CHO N02 Page 7 17. An alkene with the molecular formula CsH14 is treated with ozone and then with zinc and acetic acid in water. The product isolated from these reactions is AW/Wo D What is the structure of the alkene? was? (re? IV V 18. Which reagent(s) given below could be used to synthesize c_is-1,2-cyclopentanediol from cyclopentene? A) KMnO4, OH‘, 5°C C II B) ,then H30+ HCOOH C) H2304 D) All of these E) None of these 19. Which reaction will yield CH3CH2—D? A) CH3CH3 + D20 B) CH3CH2Li + D20 C) CHaCHzOLi + D20 r D) CH3CH2OH + D20 B) More than one of these Page 8 20. The structure of the product, C, of the following sequence of reactions would be: NaNHg CH3CHgBr H2 C5H5CECH ———> A é» 13 —~—- (3 liq. NH3 NizB[P-2] Note: catalyst for the last reaction is either Ni2B[P-2] or Lindlar's catalyst Pd, CaCO3, quinoline A) c_is—CH3CH2CH=CHC6H5 B) c_is—CH3CH=CHC6H5 C) m—CH3CH2CH=CHC6H5 D) C6H5CECCH2CH2BI‘ E) C5H5CECCH2CH3 21. What is the chief product of the acid-catalyzed hydration of 2-methyl—2-butene? CH3 A) I CchHCHZCHZOH CH3 B) CH3CHCHCH3 OH OH C) l (CH3)2CCH2CH3 CH3 D) | HOCHZCHCHZCHg CH3 E) CH3C-CHCH3 HO OH 22. How could the following synthesis be carried out? J1] *L/T A) (1) Brz/CC14; (2) CH3CH2MgC1 ether; (3) CH30Na/CH30H B) (1) HBr, 80°C; (2) (CH3CH2)2CuLi, ether C) (1) HBr, 80°C; (2) Mg, ether (3) CH3CH20H, then H30+ D) More than one of the above B) All of the above Page 9 23. The addition of bromine to cyclohexene would produce the compound(s) represented by structure(s): H H H H H I II III A) Ialone B) H alone C) II and III D) III alone E) I and II 24. The reaction of l-butene with HBr 1n the presence of peroxides yields l-bromobutane. The mechanism for the reaction involves: " A) attack on the alkene by a Br+ ion. B) attack on the alkene by a HJr ion. C) attack on the alkene by a bromine atom, Br-. D) attack on the alkene by a hydrogen atom, H-. E) isomerization of the 2-bromobutane produced initially. Page 10 25. A good synthesis of (I {enghcw-<::::>——c0rg wouldbe: O H A) CH3CCl (CH3) 3CCl Benzene ———+ —) AlCl3 AlCl3 O H B) (CH3) 3CCl CH3CCl Benzene —> —) AlCl3 AlCl3 O H C) CH3CCl (CH3) 2C=CH2 Benzene % —) AlCl3 HE D) More than one of these E) None of these 26. Which carbocation would be most stable? ‘CH2 CH3 CH3 .3. 4. | | H Ill CH3 CH3 4, | + IV V A) I B) 11 C) III D) IV E) V Page 11 27. Which structure represents (S)-2—bromobutane? 9.“: EH: 5 Hflflr 33(ng CHKQ’Br TH? 13”“ l”2 CH3 CH3 CH3 I II III A) I B) 11 C) 111 D) More than one of the above E) None of the above 28. The most stable conformation of c_is-l-t_er;t-buty1—2-methylcyclohexane is ihe one in which: A) the m—butyl group is axial and the methyl group is equatorial. B) the methyl group is axial and the m-butyl group is equatorial. C) both groups are axial. D) both groups are equatorial. E) the twist boat conformation is adopted. Page 12 29. What would be the major product of the following reaction? EH 3 I: K] L} '2 CH3 CH5 CH3 , Cl CI ,6! CI H II! cI-IJ 'Cl 30. Select the structure of the major product formed in the following reaction. CECH + 2 HCI ——u HC=CHCI CCI=CH2 CHZCHCIZ I II In CHCICHZBI : ,mch3 : , IV V Page 13 31. How could the following synthesis be accomplished? OH I + Erlflfi‘ilfli’fifll’ ‘Ifr'fal'ff’lOH A) (1) C12/hv; (2) t—BuOK; (3) peroxy acid; (4) NaOH, H20 B) (l) t—BuOK; (2) Clz/hv; (3) peroxy acid; (4) NaOH, H20 C) (l) H30+; (2) t—BuOK; (3) peroxy acid; (4) NaOH, H20 D) (1) Clz/hv; (2) peroxy acid; (3) t—BuOK; (4) NaOH, H20 E) (1) Clz/hv; (2) NaOH,H20; (3) t—BuOK; (4) peroxy acid 32. Which reaction of an alkene proceeds with anti addition? A) Hydroboration/oxidation B) Bromination C) Permanganate oxidation D) Hydrogenation E) Epoxidation 33. Which of the following would you expect to be aromatic? 4.. m D“ U l [1 ll! 34. A reaction under kinetic (or rate) control will yield predominantly: A) the most stable product. ’ B) the product that can be formed in the fewest steps. C) the product whose formation requires the smallest free energy of activation. D) the product with the greatest potential energy. E) the product with the least potential energy. Page 14 ./' 35. it. . does not undergo the Diels-Alder reaction because: A) ring systems cannot function as the diene component. B) it cannot adopt the s—cis conformation. C) it lacks electron-withdrawing groups. D) it lacks strong electron-releasing groups. B) the two double bonds are fithher apart than in a non-cyclic conjugated system. 36. Which statement(s) is(are) true about the reaction of bromine with isobutane? A) Bromine selectively abstracts the tertiary hydrogen. B) The transition state of the rate determining step is product-like. C) The major product formed from this reaction is l-bromo- 2- methylpropane. D) A) and B) E) A), B) and C) 37. What would you expect to be the major product obtained from the following reaction? Page 15 38. Reaction of sodium ethoxide with 1-bromopentane at 25°C yields primarily: A) CH3CH2CH2CH=CH2 B) CH3CH2CH=CHCH3 C) CH3CH2CH2CH2CH3 D) CH3CH2CH2CH2CH20H E) CH3CH2CH2CH2CH20CH2CH3 39. Cyclohexene is treated with cold dilute alkaline KMnO4. Assuming syn addition, the spatial arrangement of the two hydroxyl groups in the product would be: A) equatorial-axial B) axial—axial C) equatorial-equatorial D) coplanar E) trans 40. What is the major product of the following reaction? C _ H H2504, H20 3 _ H9504 ' H H / OH OH H I II III H N V A) I B) 11 C) III D) IV E) V Page 16 Part II. I. For each of the following pairs of molecules or reactions, circle: 1. The molecule with the most acidic proton (starred); explain briefly: H w E H 2. The more stable molecule; explain briefly: o © 3. The faster reaction; explain briefly: (no need to show the products) H20 CH3-CH2—Br + NaOH ——-——)-- and H20 CHa'CHz—Br + NaSH —> 4. The faster reaction; explain briefly: (no need to show the products) I .flfi and CH2 I + II _» CH2 l? 5. The stronger base; explain briefly: w n1 w H3C‘ ‘Q—NHz and H3C‘CP‘QI‘OH H H H I-O—I 6. The more reactive alkene towards H—I (hydrogen iodide) ; explain briefly: H C HC H 3 :_ H 3 >—< and H H H3C H 7. The more stable carbocation; explain briefly: 6) fi Q 11. Show the products of the following reactions. If no reation takes place, write “no reaction”. 1. _ KM o H30‘CZC‘CHZCH3 JL» n 4 , "‘1' “”3 cold, basic A B Show structure and stereochemistry of A and B. >=< HCl ——> 3. No need to show stereochemistry of the product. 4. TH3 TH“? H3C— C—C—C— CH3 KOH I I I beat H Br H 5. OCH3 _ HN03, H2304 —b- CH3 III. Propose a reasonable mechanism of the following reaction, showing every step (no need to show arrow-pushing): 9H3 9H3 H3C_9—Cl H30_ _CH3 G CH3 —+ AICI3 $0110 IV. Show an efficient synthesis of the following molecules from the indicated starting material and any needed reagents: 1. H30 from HSC—CEC—CHS Cl 2 l ”3 from (2 N02 3. HO-CHZCHZCH3 from CH3-CISHCH3 HO 2L E: 3E 53 fig Ea E“: SE SE $2 $3 kg 3%“ E2 39%“ .aflséngmHEHmfl L:— 02 35— En— mM *0 xm E U Eda :Q 2 3 mn— £._. Egmfiaéfiufieg E: E: z: :3 mm mm 5 mm mm E mm mm. 5 am a: 22333 “523,: @2me mUEEUfiLn .mEEm}... 2534. so :EmflEEaU 3+: 1:: $32 3:: 3mm: XE: $.93— mm.E_ 232 £2 5: 3+: 3:: 2.21 m5.oomuflfiwwfifluwmacnmfim 3.. n> E... ._m_ DI D ,,n._. um”. :m. Em En. t2 ._n_ $0 323.55% Fh ah mm mm hm mm mm Tu mm mm PM mm mm mm HEEEEfiHEEEmEEEE mmtm m mfl_:.m_.,_.._:.mn_ km meE mam mfimficwfia :_ Ema—E32 5.2 5.2 n. n. NFF FFF 5.: ma: 5.: :52 WE Ea 52 E: 3me an”; o :2 m... cm was E “Ema E a: E: E: 2: a: a: E: 91 mm 5 . 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