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old exam 2 - 180-222B EXAMINERS: Profs. D. N. Harpp and J....

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Unformatted text preview: 180-222B EXAMINERS: Profs. D. N. Harpp and J. A. Schwarcz ASSOCIATE EXAMINER: Professor M. Damha Part I Version 1 Part II 1. Seat_____ 2. 3. L06 -—-— Total LAST NAME FIRST NAME STUDENT NUMBER FACULTY OF SCIENCEm-FINAL EXAMINATION CHEMISTRY 180-2223 ORGANIC CHEMISTRY II DATEzTues. April 15, 2003 2:00 - 5:00pm INSTRUCTIONS: 1. Fill in your name and student number on the answer sheet provided; make only one answer for each question on the answer sheet. Be sure to fill in the "check bi " as well. Answer all 35 multiple choice questions on the sheet provided. LL93 QUEST ALSO) Make dark marks for your answer only when you are sure of your response. Put your name on the first page of the exam as well as the second and hand it in along with the answer 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. Final COURSE results will be posted on the Web in the usual place. The final examination grades will not be posted. Calculators and simple language dictionaries are permitted. PLEASE DO NOT ASK QUESTIONS OF THE INVIGILATORS ABOUT INTERPRETATIONS OF THE EXAM QUESTIONS. IF YOU HAVE A QUERY OF SIGNIFICANCE, PLEASE SUMMARIZE IN ON THE FRONT OF THE EXAM AND IT WILL BE EVALUATED. 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 CORRROBORATE AN INVESTIGATION OR CHARGE OF CHEATING UNDER SECTION 16 OF THE CODE OF STUDENT CONDUCT AND DISCIPLINARY PROCEDURES. INVIGILATORS: AT THE END OF THE EXAM, PLEASE MAKE A SEPARATE PILE OF THE ANSWER SHEETS. 180 ~22ZB PLEASE BE SURE TO PUT YOUR NAME ON THE FRONT PAGE OF THE EXAMINATION PAPER ON THE PROPER LINE PLEASE DOUBLE CHECK THAT YOU HAVE FILLED IN YOUR STUDENT NUMBER ON THE ANSWER SHEET. BE SURE YOUR NAME IS THERE ALSO. "xam $;'l _ ' mg-.‘jmame-' L. é-utfia ffllgwing.r&a¢tiomz .- f 3" . ’ CH3CEu—CH2 T GH-SW'W a. CHEEHCHZCHZCEzcgg CHZQH b- 0H I CHECHCHZCHZCHZCHZCHE C. OE ',CEBCHCEZQCHZCEzcang¢ I d; CHECHOC 2:32:32CES_ I §H203_ e,.CHSCH€320CHéQH2CH_ E x. TGCH23H2532§Eé 2. What start'fi prepare.} ; H" as; Elfi’i'fif.. L mywww __ ‘ ' CHJéHngcagficfi§ _'_¢B§H:Lgéfiggfihgt gfifl iii"; ' ' _.,. ! .__ _ @ffi‘n_fl ¢ '2¥ '@ECH§$%g§%¢H§gH:.'= II'tm III" IV_3£ Tu? mantra: {gozzadk Final Exam v. l-—Page 2 3. What would be the major product of the following reaction Concd. HBr(xs) C6H5CHZOCH3 ————————w————H—> heat (DQOU'ED 00000 4. Which would be the weakest base? a. p—Methylaniline b. p-Methoxyaniline c. Hexylamine d. p—Nitroaniline e. Dipropylamine 5. What would be the product of the following reaction? NaCN CHBCH=CHC02C2H5 —-————_> ? C2H5OH, CH3COOH a. CHBCHZCHCOZCZHS CN b. CH3CH==CHCOZCN c. CH3CH==CHCN d. CH3CHCH2COECZH5 CN e. CN CH3 CH=CHCOC2 H5 OH 6. An aldehyde results from the reaction of which of these compounds with aqueous base? a. CH3CH2CH2C1 b. CHBCHClCHZCl c. CHBCH=CC12 d. CHECHZCHClz e. CH3c012CH3 (@1125 Final Exam v. l--Page 3 7. How many signals would you expect to find in the 1H NMR spectrum of CH30CH2CHZOCH3? l (DQDO‘DJ 01:wa 8. What would be the final product? 0 CH3 II | RCOOH CH3OH, H+ CH3C=CH2 —-——> product —--—~———> final product a. (CH3)2CHCH20CH3 b. (CH3)2CCH3 OCH3 c. (CH3)2CCH20H OCH3 d. (CH3)2CCHZOCH3 OH e. (CH3)2CCH20CH3 4mg 9. The product, B, of the following reaction sequence, CH3] 0 1 Ag ,0 1 heat I rgun c organ c I 0 product “20 product N I CH3 0"" U I? T 1' | CH2: CHCHEGHE CH Emma}, en 3 CH 5 CH,' I II III W would be a I b. II c. III d IV e I and III only $91,224} Final Exam v. l——Page 4 10. What would be the major product of the following reaction? H+ CH3CH20H + CHZCHZ \ / O > a. CH3CH20CHZCH20H b. CH3CH20CH2CHZOCH2CH3 c. HOCHZCHZOH d. HOCHZCHZOCHZCHZOH e. OH CH3CH20CHCH3 11. A compound with the molecular formula CBHBClO gave the following 1H NMR spectrum: triplet at 53.7 triplet at 64.2 multiplet at 67.1 There was no evidence of an 'OH band in the IR spectrum. The most likely structure for the compound is: a. CGHSOCHZCHZCl b. C6H5OCHCH3 Cl c. p:ClC5§40CHzgfi3 d. g-ClCGHAOCHZCHB e. p—CH3006H4CH2C1 12. Which proton(s) of the compound below would appear as a septet in the 1H NMR spectrum? CH3 II\ \\I CH3CH2CI-Iz—O—CH fT‘i éfif’ V IV III The protons on carbon I The proton on carbon II The protons on carbon III The protons on carbon IV The protons on carbon V (DCLDO'EU {god/LP) Final Exam v. l——Page 5 13. What would be the product, L, of the following reaction? H , ' Q4“. E... K 2—”... L I H NI ©— swan-12 —© © macs-12 MHZ IV V a b. II c. III d e 14. Which of the following reactions would serve as a synthesis of butyl bromide? l reflux CHBCHZCHZCHZOH + HBr _—> 2. CHBCHZCHBCHZOH + PBr3 —_> 3. CH3CH2CH2CH20H + NaBr ——> reflux 4. CH3CH2CH2CHZOH + Br2 —_> a. l b. 2 c. 3 d. 4 e. l and 2 only [gaLELG Final Exam v. l——Page 6 15. Which Wittig reagent would be used to synthesize O/V ? CH=P(CS"%)3 6+5CH=PWEH513 O Gmsm} CHSCHZCH’tpfc‘sHs-B m IV I II III IV Either I or II could be used. mQ-OU'DJ 16. The final product, D, in the following reaction sequence, CHZCHZ \ / 3 Mg 0 H30+ > C PBr > D, CEH5CHZOH would be? a. CGHSCH2OCH2CH3 b. C6H5CH2CH20H c. C6H5CH2CH2CH20H d. 06H5CHCH2CH20H Br e. C6H5CH2CH20CH3 17. Which sequence of reactions would be utilized to convert into /CH3 O 0 c—CH3 ? CO2CH3 | OH 2CH3MgBr, then NH4+ HOCHZCHZOH, H+; LiAlH4, ether; 2CH3MgBr, then NH4+ HOCHZCHZOH, H+; 2CH3MgBr, then NHAIJr HOCHZCHZOH, H+; H Pt; CH3OH, NH4+ None of these (DQOU'DJ 2 I E60 9213 . » Final Exam v.-l-wPaqe 18_ .j' ' owing =13“- :éee'an-l tautamfiria pair? 19. a.aN==Ch=‘=M {I , RCNHBr' fll. - } ?' ¢H=¢Hmig GE's-c.3112 cm'la; I Q. . ( €67,111?) Final Exam v. l-—Page 9 22. Dissolving benzaldehyde in methyl alcohol establishes an equilibrium with what compound? 1. OH | C6H5CHOCH3 2. o [I C6H5COCH3 3. C6H5C(OCH3)3 23. Which of the following would be the strongest acid? a. Benzoic acid b. 4—Nitrobenzoic acid c. 4—Methylbenzoic acid d 4—Methoxybenzoic acid e 4—Iodobenzoic acid 24. The product, H, of the following reaction sequence, CEHSCHZBr + (C6H5)3P would be: a. CH3 l C6H5CH2C06H5 OH b. o C6H5CH2£C6H5 c. C6H5CH==CHCC6H5 J! d. cfiHSCHZCH==CHc6H5 e. C6H50H==CCH3 C6H5 I652: ma Final Exam v. l--Page 10 25. What would be the major product of the following reaction, O u 0H- CHBCHZCH > ? H20 a. CH3CH2CH20H + CHBCHZCOO' b. CH3CH2CHCH2CHO OH c. O CH3CH2CH20CCH2CH3 d. CH3CH2CHCHCHO HO CH3 e. O CH3CH2C|1HCCH2CH3 OH 26. CHZCH3 The IUPAC name of compound CHBCH2COH is: JHZCHB 1,1,l—Triethylmethanol l,l—Diethyl-l~propanol 2—Ethyl~3—pentanol 3-Ethyl—3-pentanol tertheptanol (DQOO‘SJJ Final Exam v. 27. 28. v9 17,2197 l——Page 11 What would be the product, C, O of the following reaction sequence? 0 H OH- (CH3)BCCH + CH3CH2CH a. (CH3)3CCH2CH2CH20H H+, heat ‘:CH2——+P(C6H5)3 ___> A ________> B _____________——> c b. OH (CH3)3CCHCH2CH==CH2 c. (CH3)3CCH2C==CH2 CH3 d. (CH3)3CCH==CCH==CH2 CH3 e. OH (CH3)SCCHCHCH==CH2 CH3 The product, F, of the following sequence of reactions, CH3 LiAlH4 H20 PBr3 Mg co2 H+ CH3CHCOOH _____—> A ___> B > c > D ~__> E ___> F, Ether H20 would be: a. fiHB CHBCHCHZBr b. CH3 CH3CCH2COOH Br 0. CHBCHZCHZCOOH d. CH3 CH3CHCH2COOH e. CH3 CHBCHCOOCHB [(50 was Final Exam v. l—-Page 12 29. What would be the major product of the following reaction? 0 O .u H OH' C6H5CH + CHBCH > heat a. 0 || 06HSCHZCCH3 b. o 0 II II C6H5CCH2CH c. OH OH | I CEHSCHCHZCHZ d. 0 || CEHBCHZCHZCH e. 0 ll C6H5CH==CHCH 30. How many 13C signals would 1,3wdichlorobenzene give? a. (J'lybUJNH b. c. d e I @sz6 Final Exam v. l—-Page 13 31. C6H5 i CHSCHZCHZCCH3 \ \ . Your task is to synthesize OH through a Grignard syntheSis. Which pairs of compounds listed below would you choose as starting materials? a. O CH3CH2CH2Br and CH3CC6H5 b. O CHBCHZCHZCH and C6H5Br c. O C6H5CH and CH3CH2CHCH3 Br d. More than one of these e. None of these .rL 3 H C .4 . H C I B . . . C fix . 8 [NW C r3. H 6 C ( n {go 122,6 Final Exam v. 1--Page 15 33. What product would you expect from the following reaction? enuntiomer anuntiurner IV V a. I b. II C. III d. IV e. V 34. Predict the major organic product of the following reaction: CHg—Q— angel-+0 + AgflalH3); —"'2°—> Hooc—Q—cngcoo- CH3—©—cflzc~oo' CH3—©—CGD' I II III 0 II CHs—Q—CHZCl-hOH Ho CHECHD IV v a. I b. II c. III (:1. IV e. V $311.14} Final Exam v. lvaage 16 35. What is the molecular formula of this compound? 78 MEr 79 80 81 a CEH6 b C3H5Cl c 06HB d C6H9 e C3H7Cl (301L215 Part II 30 marks total I. (10 marks) Provide a mechanism for each transformation below. 9‘3 a. O 0 0 - 0 C=O II II II Na+0CH2CH3 n I CHg-C—CH=CH2 + CH3-C-CH2-C—CH3 ---—-> CH3-C—CH2-CH2-CH-C-CH3 CH3CH20H || 0 OH b- Hs—--CH2 H4. 5 /J\/]>/ ’ 0 $02,213 2. (10marks) Provide a synthetic scheme to convert the starting material into the product shown. Use any other reagents you wish. 0 0H 0 3- t J} CH3" I —CH3 —" CH3 —CH:2' H ?H ,CHz-CH3 “BR ’0“ b. CH—CH—N C\ [CHZ‘CHg (IJH \CI-Iz-CH3 Eli-bk 3 CH3 CH2‘CH3 —l- (3:0 (to 1:113 H3 {991.128 3. (10 Marks) From the data below, determine the structure of the compound. m MmSpoctrum U in 5.. “min”! In “WMMMlmIIDIm1MIMIDM "'ii'mi _ m 3 'I on no no 270 0 In an "a an 10 a (60 L1 ‘43 LAB QUESTIONS THIS SET AND THE ONE 0N MIDTERM II WILL COUNT 10/25 Match (one response only) the following terms on the left with the appropriate term on the right. Some connections may be used more than once and some not at all. activated carbon _ 1. forms two layers. amino group _ 2. retention time water/chloroform _ 3. polarimeter water/methanol _ 4. seed crystals anhydrous MgSO4 __ 5. suspension of a liquid in another liquid azeotrope _ 6. remove colored impurities carbcnes __ 7. constant boiling point. reflux __ 8. acetylation possible. distillation __ 9. soluble mixture. emulsion _ 10. drying agent. 11. can be isolated and put in a bottle and characterized. 12. allows for prolonged heating. 13. usually permits the separation of liquids. 14. saturated sodium chloride in water. 15. reacts with alkenes. 16. reactive intermediate. 17. retention time. wk ..WE .V < an N? 9.. “Sums 3”? Sb: S2: . ma. am.“ 4 ...Eka. we ,3 .. . ..... $11». 3. ... H ‘ ‘ . 4 . an. . Em . . .‘ “5am . a man. ...E..§ 3% 4.53 33mg .. 33W.” . a. .. .. “2w... 33km. ...E? Em. .. pi”. . H . E35. C2235§3 2.5m. . 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This note was uploaded on 08/08/2009 for the course BIOL 202 taught by Professor Y during the Spring '09 term at McGill.

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old exam 2 - 180-222B EXAMINERS: Profs. D. N. Harpp and J....

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