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old exam 1 - Chem 222 FACULTY OF SCIENCE FINAL EXAM...

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Unformatted text preview: Chem 222 FACULTY OF SCIENCE FINAL EXAM CHEMISTRY 222 /,2 34/ LAST NAME FIRST NAME STUDENT NUMBER EXAMINERS: Prof. D. N. Harpp DATE: Apr. 21, 2004 ASSOCIATE EXAMINER: Professor J. Sehwarez 9:00 am i 12:00 noon INSTRUCTIONS: r-JG‘P‘E-“r‘eP Fill in your name/student number on the answer sheet. Fill in the "cheek bit” (ISI 2 initials of last name). Answer all 35 multiple choice questions on the sheet provided ( 70 marks); answer the True~False questions (#36-40, 10 marks) by using response 1 for True and response 2 for False. The 8 lab questions should be answered in the same fashion (#41 - 48) and will be counted for the lab grade. Make only a single dark marks (pencil or pen) for your answer. No cross-out of pen marks. Put your name on pages I and 2 of your exam and hand it in with the answer sheet at the end of the test. Answer Part II ( 20 marks) in the spaces provided. Exams will not be returned; final course grades will appear on WehCT in a few days after the exam. Calculators and molecular models 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 WITII UN USUALLY SIMILAR ANSWER PATTERNS 0N 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 COMPUTER ANSWER SHEETS. THANK YOU. m mmgmmmoafifi .. ,_m8?§o§-Enafiflamg‘ ‘ I . .88. 3893 mafia logowmn. 35w WWW”. . .. gmmogogaumfigw I 83.229 53% 0-0 En tlolwow mfimMm HHPFEHHnLHIIW Em: .. ‘. .. mflummwunm ..........|..11|..| E332“ Mamas : :Wwwummg .. -wm «Emu m . Em _ m ‘ F8 $8333“: __ . _ 33-333 “Ea. wwmoimmmoa “3%. m can 20 40 EU 80 130 160‘ 140 220 200 120 100 PPWI PERIODIC TABLE OF THE ELEMENTS _ Name: Date: 1. Which of the following compounds is an acetal? A) B) C.) D) F. v IQ A) El -._. C) D) E) 00 ll él {:I~I3CCI-a12CQCI~I3 l D HQK JACK ‘ CfififlgflH K%:;j:HCXEHPh3 13 Ill eluljocng (:Hfloelul3 I 11 111 IV None of these [3 || CH3CCH3 + CN‘ CH3 l CH2=CCOOH C HLzCH 1COOCH3 CchHCHg | CN CH3CH=CHCOOH None of these W . The product, C, of the following reaction sequence, HCN H20 —————> C4H7NO ———————% C wouklba H3504 heat Chflaabzl 3. The product, H, of the following reaction sequence, 0 , || CEHSLJ- CEHSCCHS would be: C5H5L‘L‘H2Br + ((151-15ng ——u———3~ F —> G —> H ether CH3 | A) C5H5CH2CCEH5 | OH O 3, || CEHSCHZCCEHE CEHSCH=CHCCEH5 C) II D D) C6H5CH2CH=CHC6H5 C5H5CH=CCH3 E) | CEHS 4. The product, K, of the following sequence of reactions CH3 i CH3CHCDC1 CH3 CHZIUIgEI r H3 0* would he? Benzene ————> I AAA—I: J A H A1013 ether OH | Hex) A ,«A H!” x ' /E ’J TX} E:;J KW Ma, «‘52:! I l H .f'r\n/«"-. O OH 0 III fig/Lag” 'a “VJLW/ I,» I U I :W V A) I B) ll C) [II D) IV E)V Ckuuzzl 5. Dissolving benzaldehydc in methyl alcohol establishes an equilibrium with what compound? OH I A) CSHSCHOCHQ D B) “ angcocng C) Q,H5C(OCH3)3 D) Answers A) and B) E) Answers B) and C) 6. Predict the major organic product of the following reaction: H 13* ”W a 0 H20 ' “Ca-- 06 a ”” Ge JJC 7? I f TEE” Hay“ 0 He I II 1"“ EOE) H35 “I III OH ,_ H "'\-\. V a.“ ' Higher” "’ L! o u A) I B) H C) 111 D) IV E)V CfieW1zaz 7. What is the final product, Z, of the following synthesis? A? fit 1 KM.D, ‘ - y _‘_ a eat, w x MY (1) L'flifiinfigflfir3, Z spy ananan mf" ‘ Dbl. heat cthcr', YB C (21' “30+ (2:: H20 fl r—x 0 x—\ it “in . a?” t H A '7‘"? 1.3—ijrAl L—Bu) “L w "i CH- LN CH . ‘>‘.\.___d (/1; { f2 KWK_A'>—LO 3, < / | H m e i m i x P“ r'" i d: jb-COLE ~L\ fl\}—-COH WA" "t WWI/fr EV v A)I B)lI C)IU D IV E)V 8. Which of the following reactions would yield benzaldehyde? OH CgHgCI—IgCl % A) H20 heat H30+ 8) C5H5CH(DCH3]3 -—-4% (l) LiAlHig,r ether (3 CEHECOOH ————————-————————+ (2) H20 D) Answers A) and B) E) Answers A), B), and C) 9. Which sequence of reactions would be utilized to convert (—1 . C H '9" i". In lo- p' a." f- 3 I (A\ A w fiwa—CH ? J R‘”I\mymg G \X” l j A) ZCHgMgBr, then NH!” B) HOCHzCHzOH, H302 LiAlH4, ether; 2CH3MgBr, then NHA,+ C) HOCH2CH20H, 1130+; 2CH3MgBr, then NH4Jr D) HOCHQCH20H, H30+; H2, Pt; CHBOH, NH4+ E None of the above '-_/ l0. A) 13) C) D H) D) A) B) C) In E) L») CLEWE =9 W112. Which reaction sequence would be used to prepare 0% .3 -- 1] other H I o + a _ a (A): MgEr' “er 23H30+ Ni A O 1 ether II [#}“€ +KHfi m J———+ & H 2: are N III /L (CGH5J3P CfiHEi—i cyclopentunone H " Ni CHgMg Br' H30+ C | 9 IV CH W I II Ill IV All of the above would yield the product. . LiAlHa (LAH) cannot be used to convert carboxylic acids to the corresponding aldehydes because: LAH is not sufficiently reactive. ' RCOOH is converted into RCOOLi. RCOOH is reduced to RCHzOH RCOOH is reduced to RCHz. RCR RCOOHisconverted into [I . CI . Identify the rcagcntts) that would bring about the following reaction: CH3CH2CH2COCI a CH3CH2CH2CHO Hszi LumiNHs I.JiAlH{OC(CH3)3]3, Cthcr NaBl'lzi, CH30H LlAiH4, other . Which compound would be most acidic? CIIRCl’lZCH‘u CH3CH=CH2 Cyclohcxane 0 ll CH3CCH3 Benzene 14” C) D) dxfinflll What would be the major product of the following reaction? CEHSCHECCHg O D || || CEHECCHECH OH OH CEHSCHCHECHZ 0 || CEHECHECHECH O [I C5H5CH=CHCH afieuALzl 15. The product, C, of the following sequence of reactions, CH3 | OH— H3O+ NaEHq CH3CCHO + CH3CH2€HO ~—————+ A ——————a B __mm4_9 C, l (-HgO) CH3OH CH3 would be: CH3 | A) CH3$CHZCHCH2CH20H CH3 CH3 | B) ‘3H3CCH:CCHEDH C) [SI-Ia .D) CH3CCH3CH3CH2CHQOH I CH3 $H3 E) CH3CCH2CHCHD | | CH3 CH3 am 2.1L E6. What would be the major product of the following reaction, CI ll DH“ CH3IZZH2CH _—fl‘ ? H20 A)CHhCThClhOPP+C§hCEbCCKT CH3CH2CHCH2CHD B) | OH O C) II CHgCHgCHgOCCHQCHg CH3CH2CHCHCHO D) | | Ho CH3 0 H E) CH3CH3CHCCH2 CH3 OH 17. What would be the major product of the following reaction? o If“: El _ if EP-CCHCH3 t or, OH p q t J 1 fi (IE—J3 U 0 if?!“ 2i I 1 firH—n.\ I I "xlll. r[EMI'.jl.“.HIIJI-|3 fll—i‘(_)>n CHIC”: «fungi/F" I ‘3“ l r” th mg B: l I} o I? “fig flea: 1; j w Fifi 33:5!” | CH— N[ J O Q If”; ;:Q':‘. N mix I 3: a; x19— CCHCHzar [/ Expo-mailer — | x. g M V A) I B) ll C) 111 D) W E)V W 5.21— 18. What starting compound(s) would you use in an aldol reaction to prepare 0 | "/3; ,«CH ‘? 3 0H o o o o O I 5| || II I: C} Ismael IECi-l-g CC) I3 crawling CC! I3 CH3 I3I'3IFI2CH2 CHEC E I! III 0 o xflwdp ll . E g + H2C=G HCLHZLHECHECFL H I IV V A) I B) H C) In D) IV E) V 19. What compound results from tho aldol eyelimtion of If) 0 CH3CCHECH2CHCH2CCH3 ? CH3 CH“K CH3 i//:\Nv (.39 E}! — kfiflo "I“ CH? a?" IEJHJ 5 E II on, ~, ‘\_ (.Ig‘x CLU 1:20 { H 33/ , \w (3st fixxfiffirifi E If s I_-\\ - CH3 Ill ‘ IV A) I B) H C) III D) IV E) Both HI and IV A) £999 and N301 (13 in N aOH) Bl'z/CCh ' CI’Os/st O4 ‘ NaHC03/H20 AEWHJN {frat-IS CHI CHc— ccogi:E H5 II III IV "u“ II] a v VH I A IV V CHECE- F5 I 0-13 i C’LLQAA" 1,2,2.— . Which reagent would best serve as the basis for a sifnple chemical test to distinguish between . Which is thc most acidic hydrogen in the compound shown? 6%QWmL21 22. The product, X, of the following reaction sequence, 0 0 II [I (1) NaOCg H5 (1) NaCIH he at CH3CCH2CDC2H5 ———-—————————+ ————————+ ————+ X (2) C5H5CHgBr (2) H30+ —COg would be: 0 A) n CHQCCHECEHS CI B) l CEHSCHECOC2H5 O C) l C5H5CH2CH2CCH3 O H C6H5CH2CH2COC2H5 O H CEH5CH2CCH3 O . H . . . , H NaUCEHS _ . 23. [he iollowmg generallzed reactlon, RI + CZHSOCCHECEN #__;, would g1ve Wl’llCh CinOH product? D R H I A) CQHSDCCH \ GEN O B) l CEHEOCCHER Cl C) ” ROCHECEN O l D) C3H50€CHCH=NR | I o N RoCCchEM MW 22—2- 24. Which of these is properly termed a "quaternary ammonium salt"? A) C113NH3+ Cl’ B) (CHahNH-z+ Cl' C') (CthI‘JH+ Cl" D) (CH;1)4N+ Cl 1:) None of these 25‘ What is the chief product of the Hofmann elimination reaction applied to the compound shown I? ‘II/ l e5 5 xx) on— \+ +/\C H3 /N\ CH 5 CH3 ”rag “Nix. :35,“ l \eeHz l/ ‘FCHS [ \x—CHE at , a / m x | [I Ill KW“ [I W” 13'43 a f ow ; IV V A) I B) [I C) 111 D) IV E') V 26. In aqueous solution, which of the following (as the conjugate acid) possesses the smallest value for pKu‘? A) CoHsNH; Bl NH} Cl (CHsCllg‘BN D} (CH3CHzlzNH L‘} CH3CH2CH2NH2 27. A) B) D) E A) C) D) 29. B) C) E) 0% 7.2.2 Which of these is the strongest acid? 0 ll CH3CNH2 0 || CH3CNHCH3 D II CH3CNKCH3JZ O C] H II CH3CMHCCH3 N113 . Which is not an intermediate in the Hofmann degradation reaction? KDH Rear-m3 ——~_~w—> 1:41qu Eirg RN=C:O FlEZI'iII-I E: 1' || [3| RENEE l:l H | RPHIDH || 0 Br RENEE 0 Which of these alkyl halides cannot be used effectively in 21 Gabriel amine synthesis? ‘ CH-3Bl‘ CHgCHgBr (CH3)2CHCHgBr CH3CHCH3 l Br (CH3)3CBr 05:59:42.2), 30. How man y 'H NMR signals would c_is—1,2—dichlorocyclopropane give? A) l B) C) D) E) Ul-ISUJN 31. Select the structure of a compound C61'114 with a base peak at ml; 43. A) CH3CH2CH3CH3CH3CH3 B) (CH3CH2)2CHCH3 C} (CH3)3CCH:CH3 D) (CH3)2CHCH(CH3)2 E) None of these 32. A compound CsH] 1C} which exhibits my two singlets in the 'H NMR spectrum must be: A) l—Chloropcntane B) l—Chloro—2,2—dimethylpropane C) l7Chloro-2—methylbutane D) 3-C11101‘opentane E} l —Chloro—3—methylbutane 33. Which method would provide the best synthesis of ethyl isopropyl ether? A) {CH‘;)2CHONa + CHsCHzBr em—> B) CH3CH20Nu + (CH3)2CHBr ———~n-~> H2304, 140°C C) CH3CH20H + (CH3JECHOH ————————————m_e H2304, 18D°C [n CH3CH20H + (Cnggcuou ——————————————+ E.) CH3CHzONa + (CH3)2CHOH —-~——> 34. Heating CH3CH20C112CH2CH3 with excess concentrated HBr would produce: A) CH3CHQOC112CH2CH2BI‘ B) B1‘ClIgCH20CH2CH2CH3 C) CH3CH20H and CH3CH2CHzBI‘ D) CH;;CllgBr and CH3CH2CH20H E) CllgCHzBr and CH3CH2CH2B1‘ 35. Which of the following acids would have the smallest value for pKu? A) CHsCOOl-l B) ClCHzCOOH C) ClzCl-ICOOH D) ClaCCOOH E) lCHgCOOH Chem 222 Answer the following True/False questions using response 1 for True and response 2 for False on the Seantron sheet in Spots 36-40. 36. Polymerization takes place when CH2=CHC02CH3 is treated with benzoyl peroxide and heated. 37. When acetone is treated with base followed by bromine, l-brornOpropanone is produced. 38. When n—propylbenzene is reacted with excess chlorine followed by base. then an acid work—up, the product has a strong signal at ~1715 cm‘1 in the infrared. 39. When C6115CH2CH3C02H is treated with SOC]: then N—bromosuccinimide (NBS), the product has diastereotopic protons. 40. A nitrene is the nitrogen analog of an alkcne. Lab Questions Answer the following True/False questions using response 1 for True and response 2 for False on the Scantron sheet in spots 41-43. 4] . Sodium dichrornate dihydrate is not very soluble in water. 42.. in the preparation of sulfanilarnide, it is necessary to protect the amino group before adding chlorosulfonic acid. 43. Celite (diatomaceous earth) and charcoal are both useful to rid the impure final products of trace particles and impurities. 44. In column chromatography, from the top of the column to the bottom, the materials that are generally used are respectively: sand or drying agent— silica gel —sand then a cotton plug or ChemWipe. 45. Most pure solids melt at a single temperature as opposed to a range of 1—3 degrees Celsius. 46. When using a separatory funnel, as most organic solvents are more dense than water, they are taken off first during this procedure. 47. In a Wittig reaction of benzaldehyde (CGHSCHO) and [(CQH5)3P+ CHchJ-L; Br '] the product that is formed is usually a mixture of diastereomers. 48. In the esterification procedure used in the lab this term, acetyl chloride is used to generate the acid tHCl') that acts as a catalyst in the reaction. Chem 222 Part 2 l. 10 marks Write structures in the boxes based on the reactions that are portrayed. No mechanisms are necessary. 1. base CH302CCH2COQCH3 —-—> 2. C6H5CH2BI' €12H1404 - s 13C signals H+/H20 BTQ/hV _ C9H9Bl‘02 C9H1002 H+/CH3OH —H20, Dean Stark Trap Base fl CIOHuBroz Chem 222 2. (10 marks) Consider the following reaction of dimethyladipate (A). When treated as indicated compound B is formed. It has the properties as indicated below. 1. base CH3OQCCH2CH2CH2CH2C02CH3 (A) -—> C7H1003 (B) 2. work-up Compound B shows two peaks above 1700 cm"1 in the infrared; the 13’CN MR shows 7 signals. When B is warmed in aqueous acid, a compound CngC) (C) is obtained with an infrared band at ~‘l710 cm‘1 and displays 3 E3C NMR signals at 27, 40 and 208 ppm. a. Show a mechanism (arrow pushing) for the formation of B from A. b. Show a mechanism (arrow pushing) for the formation of C from B. ...
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