PS_5_KEY - Suggested Carey 7th Edition questions Chapter[6...

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Unformatted text preview: Suggested Carey 7th Edition questions: Chapter [6: I625 e-k; I627; I639 Chapter l7: I727; I730 a,d,e; Predict the product for the following transformations. When necessary please explicitly show the stereochemistry of the product. Ole (i) mCPBA, CHZCIZ @- (li) HBr Me ———> W / N l M GM 0 R FlPh H (i) TsCl, NEt3 (ii) KOt—Bu, THF ————————————> (iii) mCPBA, CH20l2 "BU (iv) H20, H2804 u \I/‘Lflx A attfifié‘“ Tau, M 50%“ (i) mCPBA, CHECIZ —————> (ii) NaSMe, THF (iii) NalO4, H20 (i) mCPBA, CHZCIZ (ii) PhMgBr, Ergo / %€Bk OMB (iii) H30+ H EtOH, st04 Ph ——> Problem Set #5—vk.) f.“ v3 , I H (i) mCPBA, CH20l2 (ii) NaSPh, THF Me (iii) KH, 18-crown-6 THF , B), 6?) (iv) Mel V SPR‘ (v) H202 (2 equiv) (i) 0304 (cat) t-BuOOH, t-BuOH 4 NaOH 0 (ii) 0:0 \’/I p-TSOH, PhH, reflux O (i) NaCN, Et20, H20 Me (II)H30 Me Zn, HCI, heat Me Chm/ume (Lgbw , O HOWOH \ M W, ®Me p—TsOH, PhH, reflux i i L i l l i 3. Provide the reagents to accomplish the following transformations. More than one step might be required ; for each transformation. Gd) ML?“ 6. 0;) Mi L13 Pctfflt, swear-w, m) Mama Mach. “L. Era: MP0 (U) “mm! W F ‘ ~ law If HO oMe “ SPh W H 3 to falls To , l Era, ; Kw lSl‘U/“U% cfilfim (if) twee. ("3‘ $010“ Is this molecule chiral? Qfiv‘jkgflk'mp *— —~ M i) 13mm. sum“, UL TEMPO O . Me Q l“ ” i1 ‘Efiwm mam W Me W “lb” Me “growl H (“'Ll 0i? 1, WvglM» 4. Provide a reasonable mechanism to account for the following transformations. When necessary please explain the observed stereochemistry. Br Me HBr ONMG ’::o a . O 5” "OH Nu‘ Make sure your mechanism includes a transition state to explain the observed regiochemistry (and stereochemistry) in the product I" {,3‘ j 1* gr 1w Br A H" ,, au‘o" z; (i) PhMgBr, Et2O "1:0 .. 0 (II) H3O+ Make sure your mechanism includes a transition state to explain the observed regiochemistry (and stereochemistry) in the product :5”? as: l M“ w my“ riot-w Wfisfif’ f ? sMLullx,‘ Wm “kggr, mttfliétfiuw O NaOH, H20 HO OH Phi PhXH Eumwmbtalreb Mavuk 3(a)” ' . ~oK v saw “0 ¢ £3 wlfl H 62:1? ":1? H" Xi“! My: “ ' * ’0 ‘1 MM.“ Ph/lLH p '3th kntanmatuteb Mémtfis w”. H :0“ Z ‘ Z FMngmfi, gyro M 3:»: Ms om VCR: ‘fik/lH “V Eat.» W3“ WAN 322 Wng A.._._? EXH NM," “LL.— M (i) NaCN, Et20, H20 Ho ON Q H (ii) H30+ UH EH” n19-wa E\“* fin ___.9 U; ($0 a“ f; "a a” C: e: h “20‘” /h QM Nut” 0 EtO OEt E’EOH,H+ H E?“ H ‘ w MeO M90 H 4%,3: ,H 143 g; k'f'w an r “ a? h fig?! *; / w 51”“ gr? [:4 w “’i g2" JE-J, «*- E: [1 “45/ M“ w 0 Kg“ MD Ml? . “49/ MD a \LTRQCMZ ‘ , ab age:- a”? @‘9 .r"\ 1‘ h [I 5 A 44 4 KW? 4M H p-TSOH (cat) a rfi' PhH, reflux 633“ Jaw ,5 on M WS'M [,1 D a H30”: heat 0 ‘ WMG Me /\/ ® '5 b“ “'9 15% a AA @307 N" W" M b“ \\ S 42w» “x _. i .4. homo“ 5. Perform a retrosynthetic analysis on the following molecules (work backwards) from the given commercially available starting materials. H , H O a, L 0"?» ° / /\X M K/fi’; f” r H ’¢ W I'm/V ml Pm; cm {$.53 I) Wit, ’iL L FCC i’DC mull/x, ‘Féléwc’°\ll/ , ///}\ MWM will, L on M Kg _/ x“ K ‘ ‘- V— 0 Lu“ Oh W5 F ...
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This note was uploaded on 04/14/2010 for the course ENGL 104 taught by Professor Osbourne during the Spring '08 term at A.T. Still University.

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PS_5_KEY - Suggested Carey 7th Edition questions Chapter[6...

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