practicexamfinal - Prof. Sultwon Hong Name: PH“ DUE-F K12...

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Unformatted text preview: Prof. Sultwon Hong Name: PH“ DUE-F K12 CHM 221D Spring 2GB? UF ID: CHM 2210 Section 0766 FINAL Exam A May 2, 2007 This exam contains 12 pages including this coyersheet and three pages of scratch paper. Write your name on eyegy page. Write all final answers on this copy of the exam. Make sure that you sign the Honor Code certification at the bottom of this page. - Tum ceit phones oft and store them for the duration of the exam. - The exam wiii be ooiiected at 2:30 pm. without exception. — Piace your student in on your desk for checking during the exam. - it is okay to use a pencii. an erasahie pen ora white—out correction. — Piease remember that your exams wiii be scanned or xerox—copied. - Exam is cioseo‘ notes and ciosed hook. Moiecuiar modets in a transparent piastic hag ( without the instruction manuai) are aiiowed. A catcutator is not aiiowed. On my honor. I have neither giyen nor receiyed unauthorized aid on this examination. Signed: Page 1 Hon CHMZEiflS TFINAL—A Name: 1. {15 rats} Acetic acid can be protonated by H230. either on its doublesbonded oxygen {A} or on its single bonded oxygen {B}. _. ._ @fi _ ._ EL H2304 .' Oi - 0 3H 3 or J ._o.. /[T_o_.H Ate; H A B Eff a] Draw resonance structures of A. If no resonance structure is possible. write Hm. :5” :H’H streams} G} +@,H .1 I | H H 9 h -1 if.“ US" flr’H #3 é) '- A ( + Q. g +6 ‘) 5T1- b} Draw resonance structures of . If no resonance structure is possible, write N . 1-. I' F) It. 0 I: i ,.H H )EQEJ N / Pt car i. if H H 9 o a a 1 H c} Comparing the resonance structures obtained above {a and b}. predict which oxygen [double-bonded oxygen or single-bonded oxygen] is more basic. Explain your reasoning briefly. '1?" Stronger hassflfircle} ys. single-bonded oxygen Wh ?‘ JT"- ! The. Product: foo—meg} I7 Pretoria-Earn .4 the; Joqugcbqwj oxygen a More ml: Joe truth: resend-LE— Shbt'lt aspects :1 2. {6 bis} Follow the flow of electrons indicated by the curved arrows in the reaction below. and predict the products that result: —. + Dug/CH3 a H | H'"‘\ H E? 2 3‘“. H 3- (It?! Fits} _ - - . a] Draw a line angle tonnula Er— ' f b} Draw the-roost stateside” cor-truncation of {2R,3Rl-3-bromohex~5en-2-ol 5? _ trans-1dart-butyH-methylcyclohexane hm: H.“ i are: + i - W on: at; t _1 CH3 email : +2. ' Br __ . Page 2 Total Points: Hon CHM221D S 4]? FINAL-A Name: 4. {3 pts} Identify the relationship in each of the following pairs. Your choices are: confonners tcontormatr'cnat isomers}. geometric {electrons} isomers, enantr'omens, diastereomers, structural Jsesstwiensfl Feaeee-Jfliffieleenere Preset-tera- __ _ . __ _.. _ . .. . ._ __ .. . . a} W i 5 CH3 i Ho H g Ho H Hot ' o i H Br . i 'H ‘ O O O i e nan-H c. m e rs ‘ a ‘ all aslemnnner 5~ ,._i_2'1?.E_l§i____ __ .__.________ _. _. ._ _ a 3] Reaction of HBr Iwith {H}-3-methylhexan—3~ol leads to [fl-B-brcmo—B—methylhexane. Explain this : stereochemicai outcome or showing the structure of the trey.r intermediate. | | I {Rt—amethylhexan-Brol Racemic mixture A" 1 I '9‘. ! Optically pure I?" til-3 i .. P)! \X‘A 1%”. Hurlebfl’hh +5 I y brothels ovum E H a 5 1 '1' / L”) Dim decor I H. . _ ' ~—- “1 \w W W W | If M Ede— J 121‘? Pimp? “Fl-1* P” emote etc | SP)”- W Hell I" If hl'E'ipiain—merste'reochemisfiy on e elimination react?on Eelovi. using “Iceman—projections: I B E) E) f .- I NaoEt E E2 e lMtt‘lLfi‘m ! | | . CH3 “ a": Jar 4: r5: I En" " pk l H a _ | PH. " F P“ H 2H 9 H “i “‘3 C a “ EEG CH} t J l. | M - cof any" ErD C5311 ftp/m flfiWl-u. Page 3 Total Points: Hon CHMEZ'H] S I]? FINAL-A Name: E. (12 .ol‘s} Consider the ozonolysis of traos~4.5—dimethylcyclohexene having the configuration shown. Ho Ho Ho Ho H H H H H H H H “3‘3” 1} '33 H313 H H CH3 H30 H H "CH3 H Cw 2} ME .3443 H I: H3 H36 H H31: H H C H3 3 H H H H H H H H CHO CHO CHO CHO A B C. D Structures A. B. C. and D are stereoisorneric forms of the possible reaction product. 4?].- al Which, if ant-f. of the compounds A. B. C, and D are opticallyI active? A Anal E) “if “flu-‘5 -— 1 1: min. t— b} Are there any identical structures? . I 4'9 a MA D (Ami mm! coco). 2le 4?: c} What product is formed in the reaction? if. [16 lots} Consider the following two reaction-energy diagrams. {A} Reactant -} Products {E} Reactant' r} Products' I 11' "3'34 He] or" P l' a timer floatation Frail-us gamut-1.9.. Profit-[13 41¢ a} Which reaction {A or B} is exothennic [oH an}? E b} Which reaction {A or B]: has the transition state that is closer to the products in energy.I and in Jrr structu re“? A c} Which reaction {A or E} is more selective? Explain why in one or two sentences. A Flirt} TMEM Bin-+1 3 more PmJud- trite "M filler-g)! anal mew-re (Howmmi W flEQ {Wait-7w army} “H Fag 4 Total Points: ’5 [o gar, a B. Name: Hong CHM221U Sufi? FINAL‘A {4D pie] Draw the structures of Intermediates, or products including stereochemictry where I I appropriate. Treat each sterecieomer {including enantfomersj es_a separate product and crew rt. WrIte HR. if no reaction is expected to occur. No mechanismc are reqmred. ear ; Br 1} Hgmflc}; I on Q—/ ! H20 I "—" < A '——" . 2: NcEIH4 CH3 : mdflTl’h—CL TE)" ' " _" "—— 7 ‘3 4° : . CI cI Ho’\© ' DMSO.CH2C.12 — 'FB “‘3'. than Eta“ “Sworn finidlflon“ 5 er I {9H 0 TECI i CH - I m 3 Pyridine | Derically pure i {SHsomer . . _ _____._ __ | I “2 Percacc. I Hac'C-EC'"CH3 fluinoline CHgflH "3‘: i "Lindlar thatonI ct" I c} Br . 3F: | -—-—I- I Y [w . CCE4 TotaI Points: Page 5 Name: Hong CHM221I‘J BED? FINAL~A {30 pts} Propose syntheses of the compounds shown below. Show all reagents and conditions that you would use in each step. You do not need to draw a mechanism. Draw only the "fonuard route" as your final answer. steps /\]/\(}H -“:_'*_+ on m LE. PI IJTfi. J w 3 1,51% L 2-er /\l/\Br l} “5 u A 1111‘ 1) eso'r ' ! works? Qt” H1. (TM/Bad;th 137:. airliner-[Mt T CHE]; E“— H E: N G? ' KB” 4}” New“: I; a ___.—-I—JI of” m. E3 e3“ 5 NAN“; In} H _ ' '— —- — _ steps Ph Ph I d i Q ‘—--—*- M : G o r Sim-1M Dfirlflifi‘o'fl r: 03 l: c com.” peso, smug. cHJDL} : 1? “£13 of Pet. , CHLUIL ! n Slew-MW 3* “MGM-.131 J. H1501. Phi-ll 31* o :3 Bee" H a” U WET—f: -- Mfimvt é-“ofl LWS Aral; Page 5 Total Points: Hon CHMEE'HJS TFiNAL—fi Name: 11]. [15 pts} Addition of HBr to a double bond with an ether {—OR} substituent occurs regiosoecil‘icallyir to give a product in which the —Br and —OR are bonded to the same carbon: He r 0/0014; ' 60cm CECE“: Br . Only not formed a} Propose a stepwise mechanism using sowed arrows to show the electron movement. Be sure to shout:I all intermediates and any possible resonance structures where appropriate. Farm} ‘3 9.. Jain-ht“ @GuHfir—a :11 H. H3 (a 4, r .4. Cfiw H H fif- icuz me“: 3% lg, a.» (jar H b} Draw the two possible carbonation intermediates in this electrophiiic addition reaction. and explain using resonance why the observed product is formed. gig} The [347.th% i=5. hereon-1h cmrbot‘op‘fi'm i3. SEMI-“9951 by resoneflm or?) H Page ? Total Points: 11. Hong CHM221D Sgt}? FINAL-A Name: 1' 15pm) Addition of BrlJ'Hztj to atkenes {Halohydrin formation} proceeds Iwith good regioseleotiuity {Msrkounikou addition of DH]: and good disstereoseleotitrit}:r {anti addition}. Explain the observed regio- and diastereoseleotivity by showlng its curved-arrow mechanism. Why is 41H group added to the more substituted 3' carbon? Why -OH and —Er groups are anti (trans: to each other in the product?. CH3 Br —Etr ~ CH3 @ H20 Br [Racornioja I: Hz. Br Bf '- 3' <9 G E“. mfi Br cfi; (ls: w H2" Chechen”. G: afresh. 3 HI{/0 H :‘éfll NON? cm-Botkh‘bfi drumminer mo 30 {Mm subsFWJ GUI-ban Page 3 Total Points: Hang CHM221D SEED? FINALrA Name: 12. (15 p15,: Propose a stepwise mechanism for the following reaction. using curved arrows to show the electron movement. Please do not leave out any steps and be sure to show all intermediates and any possible reaonanoe structures where appropriate. 0 1} 2 Equw. H H3C—MgBr H ©)LC[ ——_'_h IrCHa 2} H30+ ' CH3 6) r {#10} s {#11} Page 9 Total Points: ...
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This note was uploaded on 03/03/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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practicexamfinal - Prof. Sultwon Hong Name: PH“ DUE-F K12...

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