Organic 3rd test - KEV 1 E N A M [5 R l f} mimth Fi 175‘...

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Unformatted text preview: KEV 1 E N A M [5 R l f} mimth Fi 175‘ t hm. CHE 3,1] STRY 2212 ERA 3. Nnvcmber 7. 200'? Be Sure to read cash quaazion carufully Partial crmjn MEI be assigncfi where appmpfiate, 1'0 l‘CCCiVC 11111 credit you must answer the quesiron compiettly. Only answers written in pen and in the previded answer spaces or boxes will be graded. i. (3511 aims) Write fllc maim‘ mductfor cachol'lhe follnwing P , k l. T‘sCi pyr —_.......p._ C'iLfiTEiCHECHIOH f:\ l 2. fix If” (1' CH; CH / 3 N _ (i‘E-i-‘ffiigiiTH—C\ a CHEUH .JL—a. \/ CH 0 KC“: (‘HO' CH3CH1CHWR — ("HFOH -L~+ \/ CH; O H250; m, i.‘E-i;CH:CH-;CH«UH "*——-—Iv> ' ‘ ‘ ' heat SUCL €_‘H:CH:CI-17CH1QEI ———~—a— ‘ L ' ‘ my! __ (3H - I PDCH‘ (m H“ “A / C'HflflC‘HlflH; - may —~«a> €in moi}? <X [fail-13H; u H10 \ J .. H3“: “NH F. T551 pm J 7‘ Nuf\ ' F \ / QH " HEL 3. 830' “Swat SCORE L." m in l, 10 mints-11 Write dmailcal. szepmsc mechanism {at the following transmnnution. using :31: cur’vedmx‘rnw formalism. Shaw all intermajimus. H (Lil-710‘ “\fi/l Him “5 I "' “h? ; J L439; / CHM-FHA" “lift-Sf CHSOCIILHLHLC‘nafl—lzjjr ,HJ I ‘ \ l O l . ._ “T” :Br‘f ‘ ‘ I I l 110 gméms} Win: a stepwisc synthesis that Ml! produce the given product from cyuluhexaml and any carbon compaund m‘ yam choosing containing mi; more man FWU carbon atom; You 2mm include all necessary rcagums and intermecfiimas. Youi‘ synthesis glmsf b2: aocmnplished in :3 Staps or fcwcn Credit will not be awarded for a lengthy symhcsis u. lib unnccessary steps. f i slaps ur fewer g OH m“—~—'I- ‘ CHgCH30H \ f l PmI M -— - , r \ ‘4: «73—4) ( fr“: ‘. - A l < >‘ DH 9“. 3" "'T its «Mr $122 ‘ ‘~“‘ again ‘ (‘2‘ ‘ j 6 & l {x 4" F" fl \fwflmlflifichi-i 4-H.“ EJCHACHMTEHEQ- r,“ {in l j - E LL L‘ m paints '3 Give [’L‘PAC animus {m- ihe folk‘ming Sli'Lé’ciuffib. f T tint "' EJN‘HF QV'CLQHEKKIJL EULF'Q‘LE- i W A r m WE — a w E afpowg‘waw } ,LEOPROPQKV {VCL’JFRDFRNE m. {115 _, T‘gfimph‘; :3" i153 3.7 ’7 "4mm ‘— “"' " “" c a 3 (J; H; 5L1." Em PAE’fiax-y pmsakr: J i "" 1 OCH; m m z :i—“m IF“ - A « l 3""! E‘H’LETr-H L- E— CYCLE HEXENDNE " 115C ; 1 mo w H" C'OH 77A: ‘" Z; ‘2 w is: H Y unbxv His: P» am Fm 5‘ éélj palms) Writs '4 3139mm synthesis in shew how (he ibllnwing din! can b: prepared from zhc >221":ng aster. if CH1 ‘ .é (1'H_;CHC'HEE‘DCH} W CHQCHCfigéiCil-h ? I [ OH OH OH {71,33 ‘Ca'st {Li-f3 Jr r . ' rim 5.1+ LH r ~13 - H30 3 ll ~_ «I 1»; 7T3 <_¢:__ QEEC'HLHAQ,an — k Oi DH ' 6. «’20 points] Cmnplcic [he tbijosamg m' necessary mag-em (K). or m:- "2’ F CHECUICM :— {143133011 Exeszs 4 {Hagar pmducr. 0 fl - 1 “Ha ' .V' ‘ ~ I' “74“ Q Lam,th M1; my, _._ Q :5! ~ COCHaCI H; Q" _ I x>-—:~H{::: i C‘Hgmg CHO ~OH ,H NCHJCI-I; 11‘ dctimis by writing the sign-hing :mnpound, aha M/I—CHEOH (lm C1I3CH3CCH3NH; I . CHEW; 0 if Em; H3 i ‘ U} paints) Thigh: can be prepareci from the rsaclion of firinurea u iLh an aiky! hafiide. fiviiowsd by hydrmfdc itm—pmnmtcd hy'émiysis. Write derailed. stepwise mechanism for $19 sr'z-n‘sibrlnatiun. using the curved-arrow EhmlaliSHL u 3: i (i 1 014an g V _ / x ' J _' fl / + __ ~_ A, El?“- XNH; “-—""——" Hey NI];1 LHJLILSH 1 HO”;er lhiou rca “ma r: haneihm! CH3CHAEEI H HE) mints} Wriic [he samciuz'e for [he mduci Ufthc (blinwinsz Z'CBCIEOU. L H U 0 3 _ 7 U, iL’HmCuLé : {fiber ("H «.CL' H ,CH «EU How many fignals wuuhl the producE Show in its 'HNMR Spectrum? r”! How many signals would the product shmx' in its "‘CZNMR spccu-um? 3 ...
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Organic 3rd test - KEV 1 E N A M [5 R l f} mimth Fi 175‘...

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