Summer 2003 Test 2

Summer 2003 Test 2 - Organic Chemistry Test 2, Summer I...

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Unformatted text preview: Organic Chemistry Test 2, Summer I 2003 Name: [‘35] Dr. Welis Scam=opscan* 4 +essay= CLO =- 4 + L0 = “ é? Essay 1. Consider sis-l -isopmpylnlmethylcycluheme: / 5% ((3 #GCD i :3 Draw the planar mnfhrrnatiun: Draw the ring flip equiiihu'ium (1me chair cflnfunnatifinl Indicate which 01’ these confunnational isumers is mare stable. Explain Le! W ._ LV 7 m WL L y E 4r H 61' R cm W 1‘ . W W A?“ 7K sqh WT" w (5“ r1“? Xflhm Easa)’ 2. Cnmplete the graph below. Expain. ring strain 3 4 5 *5 7 3 9 It] :1 E2 T ring size 0W w 1w hm; {0‘75"} bbwi ““jt‘i h a“ (3:: ML 5 +k'j?E.FLAr ELL-N. I3 M Essay 3. Consider the reaction below. Which substation mechanism is most liker here? Explain. 5m 2 like! We Draw the productis} resulting from this substinnion teastion indicate the steteoehemisn-y of the produetts}. Reaction: 0—H 5F /C§””0Htcnnz "-—* / \ L [ CH3 6H 3 . C(CH3);3 C(Ettg e H {EWIL Draw the mechanism of this substitution reaction. Use curved arrows to indicate el'fiztron pair movement. Show stereoohemistry of each step. indicate the rate determining step. - moieste tin},F lee}.r transition states t with [ ] andior an}.I iteyr intennedistes with [ ] Meohanistn: D It: Pigkr ) v‘ HT) 6 1". $3: WLHQME t 1. u —h (4'13 —-——e C | s...” ) mucmmfli ‘ 1‘1 i on} 4 C(CHflh L? .t I) to (1/ M \‘a ifi s “A m atfl } er .. .. '3‘ s 3’ CH3“ “g: L6“ 1 if? "- i‘i '3 3% CHEM-DI EVA 3 K "L'/ 013 L [mi-L Dev 14 a 31?": i; a 56"?" L 5s 42s Essay 4. Consider the reaction fiom Essay 3 again. Ignore stereochennstzy. These are two possible products flow the E2 mechanism. Show them. Hint: the products are constimfional isomers. Second hint: you might want to do the mechanism first. Reaction: E2 products . E; e I I." 99 obj: .oo H 52.3- F onjflc—Cfltfflsh t .J —...p.. ROD D C CH [ 3% Draw the mechanism of the E2 reaction. You may ignore stereochemism'. Use curved arrows to indicate electron pair movement. Your mechanism should account for the two products. H 1 H — T 1 * '3‘“ “1-3 H CH; ug—fi’tfl3 Lfll V t .5“ mu,qu 10m.st '\ SN ( Sift Lnflfitlfi-r f7) L The best name for the compound at the right is A. trons- l chlomfi-fiuorocyelohexane ,@ eis-l-chlorc-Eufluorocyclohexane C. from? 1 chiom4~fl uorocyciohexane U. cis-E-chloro-S—fluorooyclohexane GE) cis-i chicmfl uorocyciohexane is 2. The most stable contomation about the C2-C3 bond of butane is®descrihesd as cm; A. eclipsed E. staggered C. gauche D. aewraan @and H I H - I - a - I - r I s 1 . . . . . r . . . . . . I . I I s 4 p 4 , . . . . . . . . . . . .. Ibuprofen exists as two isomers: Swihuprof'en with [ex] = +211}. 1 U and R—ibuprofen with [o] = — fill”. The S isomer is responsible for ibuprofen’s analgesic activity. Jimmy was trying out a new catalyst designed to make oni}.r the S isomer. His best catalyst results in a product that is 55% S isomer and 25% R isomer. 3. Jimmy’s product is best described as . . A. optically.r pure B. Dpfittally quartered scalemic D. racemic E. majoritized .r‘“ L 4. Jimmyis product would have an optical rotation of' . A. +201” 3. +35“ +100 :1. c” E.—1 “ C, ELK: WISH-Z"; n 05‘; "wists U3 w 1 +(fii-6'Lch-i) 2H0“ 'l. Cousider the items in the box for questions 5 and 6. Subsu-ate CHiCHflzflTs X Nuclenplfile Nah- {b o 0~Q H—M-CH3 gun CH3CH2IDH II CH3” CH3 CH3 1.. M 7. The 5N2 reaction of [R}—2-chlorohut.sne with fluoride would result in {In L, of the sicrcocentcr. I! + '- F“ I I 'I a A.racermzat1on B.rctcnt1on ©IHVEI‘SIOH D. scalemizanon E. not enough info Consider the molecules helo‘or for questions 8 through 14. 8. D L H s» CH3 as H ‘1’}: The host name for 3 is A. chimeihyl- l .2—difluoroetl1ane E. {2.3—diR)~2.3-difluorohutanc 5 (2R. 35}2.3—difluorobutanc (2R. BED-2.3 slit] uorobutanc E (25. ESHJ-difluorobumne 10, The specific optical rotation for 9 is he: A. -s” . -2.5” DUI +2 .5” +5” 12. ll] and II are f— L, A. identical B. riot isomers constitutional isomers . onantiomcrs E. diastereomers 14. The specific optical rotation for 1] is Pic-5'3 U 513“ w w?” D. +2.5“ News L - \‘r 'WJF CHs \ {I's 111411.122?“ :6 u. [or] :?G : s FIE-H‘L‘J Jul-1.2:. . fie-“1‘” I P15” no- 54-134! “A 9. Compound 9 is chiral . a meso compo C. achiral I). both A and B E. both E and C und 1]. Sanoliare A. identical B. not isomers C. constitutional isomers (E) coantiomcrs E. diastcroomcrs 13. Patel 1] are E A- identical 13. not isomers C. constitutional isomers i1 cusntjomcrs @diastcrcomcrs 15. The best Way he make the fuel addiiive metlwl ten—truly] ether {MITRE} is l" r He ewe-v. a 4 H3 a» “haze” 16. 1|When applicable 5N1 reactions yield a racemie pmduet. Why? A. The tmnsitinun State is five cunnfinate. The intermediate is planar. m C. Ne earbncalinn is farmed. D. Hydrogen bonding prevents the ulher efififlmer fnrm being fumed. E. Suifunates are exceptionally gflod leaving gmupe. .‘ 'x Wm} MTBE want 13 TH} “I ’e j” x CH;{3=H + CH;— —-eTs e+ _ ’ n T R: “J Ail D CH3 bu” .1”, \ EH3 “D W” CH3} + -—c-—F "“ )QH (.5,ka CH ‘9” E 3 Inspect the reaetitm emirdinate below and answer questiims I? * 2t}. 17. This is the rear-firm emniinate fer an reaetirm mechanism. 45. sm he. L (B) 3N2 J {t u}. >1 "‘91 E L“ C" C. hath A and E ' L'" D. Neither A l'lt'JI‘ B 18. w represents A- print nets ('3. an“ E C. at}: D. anintennediate E. E. atransttien state Ck ' ISL 2 represents . \ A. precincts J L-\ . B- .fiGfi ' L m, M: “j J D. an intennediate fl E (E) atmnsitinn state 5 ' 2"]. 1.! represents C5,} tam-duqu 1H 13. M3“ h c. is? D. an intermediate a transitinn state ...
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This note was uploaded on 06/19/2008 for the course CHEM 227 taught by Professor Wells during the Summer '07 term at Campbell.

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Summer 2003 Test 2 - Organic Chemistry Test 2, Summer I...

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