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2212exam3keySpring07

2212exam3keySpring07 - R EV NAME first last 4 digits of...

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Unformatted text preview: R EV NAME. first last 4 digits of 531E last. CHEMISTRY 2212 EXAM ll]. March 231 Edit”? Partial credit will he assigned'where appropriate. Be sure to read each question carefully. he question completely. Relax and good Inc I! To receive full credit you must answert 1. {It} total points} Design a syndtesis of Tropinone fr may only use reagents found in th accomplish the transformation. Full ore-Cocaine using reagents found in the reagent hot-z. You e hon. but you may use them in any order necessary to credit will only tie-awarded for an efficient synthesis using fewer than 5 steps [with work-up}. Write the step~hy-stc11 reaction= showing the intermediates, and write the reagent from the host above the arrow fur each reacliou step. Then, summarize the reagents used [in order- by their number) in the boxes provided. CH; CH; Ni! NJ, EfiUCH . - ' -‘ , ct G 1? Al . H i g - Pu OH — CHyfll-t cocaine ' DCPh Hopinone 6. FCC , CHgfli; 'r'. heat Id! 3. ere... _. H' 5. FBI; (203.1-1' 9. Mg, E130 ls‘l 3. Nam-t H30. heat It). NaBi-It ._ EtGH Over-at! Rea ction' IJI TOTAL Summsn of res cuts used Hit! in ooh-.as many as too used : last step} t first step 2. (8 lutnlpoinls}: _ . The firflu’fiing pésuh's'fiflnefl mfihy] .befizaaie‘s differ in: their reafiififi' m saponificatiun. Ran]:- Iheae £31675 fmm mas! easil3r'sapunified=-{Harlem easily samnified {43). QCEGHEI ccfirg E'QECHE {id-20H; if II J ‘3: (\I I. | ._-4 3 i- 4}- 3, [filigtalspuimsj- Gijfie the IUPAC namés 1' Dr'fl'if 'fnllufirin g' mama. Ti {2 “Km El- -‘Emma'Ec—:N1t:-YL LH-mm be “BEN 16:; FFNHH'FBREBE 1.31" DI'N E‘TH‘I'LHEKF‘HHMI EE' E‘n'i"? L LYLLflflUTuz- EHE mammmrg 4'. {Emmi paints} HOW Ell-{ifliifléd’ififihanfmn Elwin-fin HEW {filiunfing-Ieactifln: fl. {8 this] paints} Propuaa a detailed mechanism 1‘5 shwing even 5133} using tuned arm“ immalism fflrthe fulldwing martian: 15, {-15..pninis.3.. . . ' ' ' rm; ; 'n flit-minimmeriaks), newsman reagent: 5'3: or-majfirspmdm-‘HEJ “m“ “mm “m" step-reaminns. I .- :fifl Gr 6:? 1. mawemar. _- . CH3 2.: H501 [iv] Q a Mimi);— 0 (“x/HRH Mflififlah [v] 9- “ ”cw. CH'qGH W 0h _ *- {IT Lat“; Rfiflh Fifi t UH 1 {15 paints) PW 1113 flafli'ng malf'riflliSL nicessaj'j. 382292111153, BI. majflr pmd'iacti s} fifth»: following with . map reactions. ' ' m . I———. _ as T‘i-P‘E‘: : i ' . . ' dNE, nwfinflfl. ’1‘?” . _ _ ; _ Enema. . . . '3 ffilflfi' 'i. Haas-$31; ——iI- Excess NaOH 2; Hgfl-F W.) D D .1532} E! H ,. . .. _ _ . - -..;- . . “i z w. :NhflEtEtfll-t. Etc/\(JLGEI a?” ' ' ' ' ' ".-_ 'CcfiEt 5 '91! I. [133 points) Ptaefii'et themg materielIS),.nee¢eseat‘gc-te;tgentts}, 'eizr nit‘tjttr pfhtt'uhte} ef the ffifiufi‘ihg fitterswp fiafififififi 'i} LEA. THE [2: thew . Him; atarfitig mm is a manusubsfitmed goth: 9.-. {12 [mal pointej _ mew the maid:- prp-duc‘ts afthe fallflwistg'wefitjfifia'in the Wei proxfieied. __ “ii-CH5}: ”V G Wee LiA1H4- ...
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