PS_15_KEY - Problem Set #I 5 Suggest the best...

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Unformatted text preview: Problem Set #I 5 Suggest the best polymerization conditions to access the following polymers. 44’ EM Li /\CN «WM I M: NC " OAc MeMe AcO n CN HO EtOJ 0” OEt n 2. Predict the product for the following transformations. When necessary please explicitly show the stereochemistry of the product. H2N NH2 ol mer' ation U + C|\“/©\KCI Lil—J; O O O CF3803H —-———--——> D (strong acid) o KOH I) —> O .. OH polymerization . O + HO\/l\/OH ' O h 3. Perform a retrosynthetic analysis on the following molecules (work backwards) from the given commercially available starting materials. H2N\/\/\/\NH2 :> M Balmsolul’luglgg H2, 7,“ a. ll WNW!” NEOWQ’ kl ram tn, m MACH l l w all Wall FmWa/Ltl dfilmdl‘a»: Nam we W WM ——————> \/\ CM /\1/ C‘\Mgl EMF k1, N“ am“ MK KwNM/V ?-v nun-h HOZCWCOZH :> M 122M223 “Mg (:3 KW; Ma»; Nam How/VV M“ L: “QM 0‘4 f... («A qu if?) 5439+ EMF \ H1591“ \/ Q, ‘ will“ Q\ Mim/ M EfiWRAs‘) ch‘bawx a" C\\/\/\ Cl M “mm “New wwm (m. we“); . 33M- ” 02,3me é—-—-——-————-("\N> W’ “‘1 MC,“ 5110 K A 0/} “3‘53" 4 m———A A w—wufv__ .. MAW. ...,u A A 4/44 4 4 4. Provide a reasonable mechanism to account for the following transformations. When necessary please , explain the observed stereochemistry. ; Cl 0 , N \ N NaOH, H20 N NH , —> i </N I J heat </ I J g H N H N H0 O N NH ' H N H+ <’ | O 0' HO N N/J ('1) Hz0 I :0: l 6:“ OH OH 6% 9“ UN w ‘4 W)" "° Kwéfiw“) W) W M . ._$._.h “” 'E‘Q" ‘33 We? (Qt; _ N (L 7/“? E an em QW 0 M‘ my” + 0?“: <1 ‘ w M " (5.190 a .1 @fi‘éfi ‘3 w) 9'0 m“ N L (“1.33 5? ha: “a? 9);” T1" é...” ’ + EL H30+ —> H H OH OH Please suggest a mechanism for the following cross-linking procedure OH OH OH HO H3O+, heat ' ——-> Walkmwgw OH 4., s ® N n \ aziml’lym “7 n :53}? x“; hi): <1,is 0g“ ~——'9 :29 ( RAH e.—~ l" U "—9 o’l “my 3U} ‘3 a o a" Q) 3k 2‘. 0‘" :I‘. cw h m g; m... r —‘). L on firm-'— g % W V” (a?) U: $42 Hw— om, ‘l 1 3| '7 m 5..., 0‘4 Cl AlBN,PhH Cl CN —> /J\C| heat CI Cl 0' Me Me n WRAQNXM' flip cam W I] E» W '9 M an *3 {1. W3 " \/ .0 L N __. L A. THF H mohmgm s M L; KM“) 5” L2 é?) W U 144391 60v.” 0" M993“ J M f\l/ é-M no W 1? \Q \" H g: 9! I“ ‘ j \‘ m :6 DN \9 w? ‘3 Mm‘f 0 0"“ 952M“ 6 “A gm C? HQNW flu! fun (:0 fiww D fifi O h F's? DI oJé; h f3} q» as) kof/ Q K'PZUH 0 “Si/vb”! o 0 C1 a?“ a UN 5 (WE-C. 51"“ Ho “ l7 l2 H2N mmm‘m WMLFHAA: (Mton wMW%0MW\ “M; «3“ EM i g ~> ‘3 '3“: "Pk fl Ms» “E Ly}: “” Ex 6”"- m '1“ L év _ UV (/3 Q ML 9 5.‘ “06% Ex £5: I ~ m (“3” 51 k? 31 a “6:? ‘3‘ “a m . ‘ ‘ _ _ 0+,“ I w M t) \ \y/IQV’“ Jk , “v ”’ ‘ MV“! 6:.”- : wwflf W WQW I3 m . ‘ an»? r fifi’ ‘n—j ‘ l4 0 1 Ar \“ 6YD® i m . A” M02155? <5: > M? W 41>. ...
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PS_15_KEY - Problem Set #I 5 Suggest the best...

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