CHEM212FINAL 4

CHEM212FINAL 4 - LAST NAME FIRST NAME STUDENT NUMBER...

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Unformatted text preview: LAST NAME FIRST NAME STUDENT NUMBER FACULTY OF SCIENCE DEPARTMENT OF CHEMISTRY FINAL EXAMINATION- Version 1 CHEMISTRY 212 EXAMINER: Profs. H. Sleiman and D. N. Harpp Friday, December 21, 2007 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 (including 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 guestions. 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. Name: Date: 1. Which is n_ot an example of resonance? I CH2=CH—CH2 - <——> - CH2—CH=CH2 + 11 Q/CHz <—> 04342 CH2 CH3 0+ «—» 0: IV CH2=CH-CH-CH2CCI3 ‘—> CHz—CH=CH—CHZCCI3 A) I B) 11 C) 111 D) IV E) None of these are examples of resonance 2. Which would be the best synthesis? ? CH2=CHCH3 —n- THZCHCHZCI I Br Br A) Brz, CC14 C12, hv Propene ——-—-— —.—_..—.... B) C12, 400 °C Brz, CC14 Propene -———+ —-—n-— C) HCl Brz, hv Propene —I-— ——a- D) NBS, CCl4 C12, CC14 Propene —-—i-— ——h- E) C12, CC14 NBS, CC14 Propene ——)-— -—p 3. Which compound would have the highest boiling point? A) CH3CH2CH2CH2CH2CH3 B) CH3CH20CH2CH2CH3 C) CH3CH2CH2CH2CH20H D) CH3CH20CH(CH3)2 E) CH3OCH2CH2CH2CH3 4. What would be the major product of the following reaction? Hac H CN ‘ H\\ l/Br 25°C I II H30 CN H30 H III IV A) I B) II C) III D) IV E) Equal amounts of I and III 5. What would be the major product of the following reaction? m NBS.ROOR 9 light ' Br Br Br‘©_\_ Ox m I II I mm R Br IV V A) I B) II C) III D) IV E) V II 6. The correct sequence of the ions shown, in order of increasing basicity, is: A) CH3CH2:_ < CH2=CH:_ < HCECF B) CH3CH22' < HCECF < CH2=CH:' C) HCEC1_ < CH3CH22_ < CH2=CHI_ D) CH2=CH:_ < HCECF < CH3CH22' E) HCECT < CH2=CH:_ < CH3CH2:_ 7. c_is-1,3-Dibromocyclohexane is represented by structure(s): Br Br H H Br Br H H Br Br H H I II III A) 1 B) If C) II] D) II and III E) Iandll 8. 10. 11. The synthesis of an alkyne precursor to 2,2-dimethylheptane is accomplished most effectively by the reaction between these two reagents: A) CH3CH2CH2CECNa and (CH3)3CBr B) CH3CH2CECNa and (CH3)3CCH2BI‘ C) (CH3)3CCECNa and CH3CH2CH2BI‘ D) and E) HCECNa and (CH3)3CCH2CH2Br . Adding sodium hydride NaH to ethanol CH3CH20H would produce: A) B) C) D) E) CH3CH20CH2CH3 + H2 CH3CH20CH2CH3 + NaOH CH3CH20Na + H2 CH3CH2Na + NaOH CH3CH3 + NaOH The correct name for the compound shown below is: Br Br/Q/ N H 2 3,4-Dibromoaniline 2,4-Dibromoaniline 2,5 -Dibromoaniline 3,6-Dibromoaniline 2,6-Dibromoaniline A) B) C) D) E) The compound 4-bromo—1-propylbenzene is best made from benzene by the application of these reagents in the order shown: A) (1) Br2,Fe (2) CH3CH2CH2C1, A1C13 B) (1) CH3CH2CH2C1, A1C13 (2) Br2,Fe C) 1) CH3CH2CCI,A1C13 2)Br2, Fe 3)Zn(Hg),HCl II 0 D) 1) CH3CHZCCI, A1C13 2) Zn(Hg), HCl 3) Brz, Fe ll 0 E) (1) (CH3)2CHCl, AlC13 (2) Br2,Fe 12. 13. 14. 15. Which is the only one of these reagents which will react with benzene under the specified conditions? A) C12, FeCl3, heat B) H2, 25°C C) Brz/CC14, 25°C, dark D) KMnO4/HzO, 25°C E) H3O+, heat Which reagent would convert 1,3-octadiene into 3-octen-2-ol at high temperature? A) KMnO4fOH B) H2, Pd C) H202, then H30+ D) Clz/H20 E) H30+ The most stable conformation of Q-1-gt_-butyl-2-methylcyclohexane is the one in which: A) the m-butyl group is axial and the methyl group is equatorial. B) the methyl group is axial and the tirt-butyl group is equatorial. C) both groups are axial. D) both groups are equatorial. E) the twist boat conformation is adopted. Which of the following dienes would you expect to be the most stable? A) CH3CH=CHCH=CHCH3 B) CH3CH=CHCH2CH=CH2 C) CH2=CHCH2CH2CH=CH2 D) CH2=CHCH(CH3)CH=CH2 E) CH3CH=C=CHCH2CH3 16. Which of the following would you expect to be antiaromatic? @D®U©©® I II 111 IV v A) I B) 11 C) III D) IV E) V 17. Which is the strongest acid? A) CH3CH2CH2CH2CHFC02H B) CH3CHB1‘CH2CH2CH2C02H C) CH3CH2CH2CHC1CH2COZH D) CH3CH2CH2CHFCH2COZH E) CH3CH2CH2CHICH2C02H 18. Which of the following is NOT true of benzene? A) Benzene tends to undergo substitution rather than addition reactions, even though it has a high index of hydrogen deficiency. B) All of the hydrogen atoms of benzene are equivalent. C) The carbon-carbon bonds of benzene are alternately short and long around the ring. D) Only one 0-dichlorobenzene has ever been found. E) Benzene is more stable than the hypothetical compound 1,3,5-cyclohexatriene. 19. Compound C has the molecular formula C7H12. On catalytic hydrogenation, 1 mol of C absorbs 1 mol of hydrogen and yields a compound with the molecular formula C7H14. On ozonolysis and subsequent treatment with zinc and acetic acid, C yields only: 0 We The structure of C is: mM—Q 0/0 N v A) I B) 11 C) III D) IV E) V 20. Which of the following statements about cyclooctatetraene is NOT true? A) The compound rapidly decolorizes Brz/CC14 solutions. B) The compound rapidly decolorizes aqueous solutions of KMnO4. C) The compound readily adds hydrogen. D) The compound is nonplanar. E) The compound is comparable to benzene in stability. 21. 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. 22. A good synthesis of E? (CH3)aC—©—CCH3 would be' A) W CH3CCI (CH3)3CC1 Benzene —> —-—>- AlCl3 AlC13 B) (I'l) (CH3)3CC1 CH3CC| Benzene —-a- —)-- A1Cl3 AlCl3 C) E CH3CCI (CH3)2C=CH2 Benzene ——-> ———n- AlC13 HF D) More than one of these E) None of these 23. What would be the major product(s) of the following reaction? COZH Q HMO3 9 N02 H2804, heat oozH 002“ COZH COZH Ctr“? Q E: 0%: No2 N02N02 OQN No2 N02 I II III IV A) I B) 11 C) 111 D) IV E) Equal amounts of II and IV 24. Which of the following dienes might react with bromine in CCl4 to yield 2,5-dibromo-3- hexene? A) CH2=CHCH2CH2CH=CH2 B) CH2=CHCH=CHCH2CH3 C) CH3CH=C=CHCH2CH3 D) CH3CH=CHCH=CHCH3 E) CH3CH=CHCH2CH=CH2 25. Which reaction would n_ot be a method for preparing 5-methyl—1—hexyne? A . ) WW 1) NaNH2 (2 mol), 11q NH3 2) NH4+ HCECNa + Cl ——> C) /l\/\ U + HCECH —> D) 1) NaNH2 (3 mol), liq NH3 Br ———-—b— + Br 2) NH4 E) Br . W 1) NaNH2 (3 mol), 11q NH3 ————~b— Br 2) NH4+ 26. Which of these dienes can undergo the Diels—Alder reaction? A) 1,3-Pentadiene B) 1,4-Pentadiene C) 1,2—Butadiene D) 1,4-Cyclohexadiene E) All of the above can undergo the Diels—Alder reaction 10 27. The molecules shown are: 2H3 L1 CI ? H Cl F CH3 3:3 313 A) enantiomers. B) diastereomers. C) constitutional isomers. D) two different conformations of the same molecule. E) not isomeric. 28. What is the chief product of the acid—catalyzed hydration of 2,5-dimethyl-2-hexene? A) 2,5—dimethyl-1-hexanol B) 2,5-dimethyl-2—hexanol C) 2,5-dimethyl-3-hexanol D) 2,5-dimethyl-2,3-hexanediol E) 2,5-dimethyl-3,4-hexanediol 11 29. Which diene and dienophile would you choose to synthesize the following compound? \/ H / “C H O [H ’/ CHO CHO ECHO CH0 CH0 I II III @CHO T OHCI CHO CHO IV v VI A) land VI B) 11 andV C) 111 and IV D) IV andV E) land III 30. We now know that the two Kekule structures for benzene are related in the following way: A) They are each equally correct as a structure for benzene. B) Benzene is sometimes one structure and sometimes the other. C) The two structures are in a state of rapid equilibrium. D) Neither of the two structures adequately describes benzene; benzene is a resonance hybrid of the two. E) None of the above 12 CH3—CH=CH—CH—CH=CH—CH3 l l l 4 Which hydrogen atom(s) of I H III IV is/are most susceptible to abstraction by free radicals? A) I B) 11 C) III D) IV E) V . A thermodynamically-controlled reaction will yield predominantly: A) the more/most stable product. B) the product whose formation requires the smallest free energy of activation. C) the product that can be formed in the fewest steps. D) the product that is formed at the fastest rate. E) the product which possesses the greatest potential energy. . Which of the following would you expect to be aromatic? ® H Q be H ©<H Go I II III IV V A) I B) II C) III D) IV E) V 13 34. What would you expect to be the major product obtained from the following reaction? 0 Q—JNQ —;>HN° ? H2804, heat No2 O N o 0 j o 2 HN—© HN HN Q 02.33 Q © I II III A) I B) II C) 111 D) IV E) V 35. (j 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 apalt than in a non-cyclic conjugated system. 14 36. Which carbocation would be most stable? (‘DCHZ CH3 CH3 CH3 CH3 0 0‘9 b o 0 G) G) I II III IV v A) I B) II C) 111 D) IV E) V 37. Which structure represents (R)-1-ch10ro-1-fluoroethane? E E 9H3 CI>Z|<H H>T<Cl H>'l<0| CH3 CH3 F I II III A) I B) 11 C) III D) More than one of the above E) None of the above 15 38. 2-Bromo-4-nitroaniline is: Br Br NH2 Br No2 I)“ NH2 No2 HZN I II III 00:43 Br Br\© H300~ : No2 No2 IV V A) I B) 11 C) 111 D) IV E) V 39. Which would be the major product(s) of the following reaction? HO O I-INO3 ,, —)- . st04 HO O HO O HO O No2 N02 H038 1 II 111 A) I B) II C) III D) I and II in roughly equal amounts E) I and III in roughly equal amounts l6 40. Which reagent(s) would you use to carry out the following transformation? ethylbenzene ——> 2- and 4-chloro-1—ethylbenzene A) C12, light, and heat B) C12, FCCl3 C) SOC12 D) C2H5Cl, AlCl3 E) None of these 17 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: HH* HH <2 Q 2. The more stable ion; explain briefly: “Hz NH; (9 and GH H Br C) BF 3. The faster reaction; explain briefly: (no need to show the products) CH3-CH2—Br + Na] ——)F and H30’ \CH3 __h_ DMSO CH3—CH2_BF + NaF 4. The stronger base; explain briefly: H H | l H2c=CH—CH2@ Na (9 and H3C—(I3—CI39 Na 69 H H 18 5. The faster reaction; explain briefly: (no need to show the products) 0 6. The more reactive alkene towards H—I (hydrogen iodide) ; explain briefly: H 30 H H3C H and H3C H H H 7. The molecule which reacts fastest by an SNl mechanism; explain briefly: Br Br 0 II. Show the products of the following reactions. If no reation takes place, write “no reaction”. 1. KMnO4, cold, basic H3C-CEC-CH2CH3 _,Na —_—b_ liq. NH3 Show structure and stereochemistry of A and B. 19 Ex.) CH3CHZCHZCI (3 _—b_ AICI3 3. H3C\ _ [CH3 1. 32H6 ,c-q —)- H 0sz 2. H202, NaOH Show stereochemistry of the product. 4. Elir H .—’ heat 5. OCH3 Brz, FeBra —_.—>_ N02 20 IV. Show an efficient synthesis of the following molecules from the indicated starting material and any needed reagents: l. o 0 Q from E: NO 21 3. HO_CH2CH2CH3 from CH3_(|:HCH3 H0 22 3 & .Ewnssc moEum Egg... BEEEQEEE a... ma Em; “an: mcofizmfimu Q35 9: mc.mmm 2mm. mmodmm D an_ E. mm Fm um mmtwm wfiEnofiur 6539...... $59.... so co_mm_EEoo 3...: 33... NE... w...omm.§$m.w..o.ée§ .wnBofl .3593 am mm mm .323 mfimfi .3... .o 9.35.... .3 3.02.50 muggy... 2E3... mm;me mEcmfic M. 2m mama. m5... fluwficmfia _.._ 9.32:2 .33 am“. am“. 3...: 3m: . 33.5 was. $5. .2... E... 3 n; a .fi .5 3m. Em E... F E I. mm an E Ema. EN. .3“. .3“. .5“. :2. an“. an“. E: E: t: m... E: am... an“. 3;. $3.8 E...“ 3...; We.“ 3...... 3...... 2m. 2... 2... 33. $.32 $2. .32 $3. mama. mm .. mm mm 5 m an an .2 an E. E m... m... 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CHEM212FINAL 4 - LAST NAME FIRST NAME STUDENT NUMBER...

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