nefziMid2winter06

nefziMid2winter06 - Student Name: Problem I A] Using...

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Unformatted text preview: Student Name: Problem I A] Using Streeker synthesis and appropriate reagents and techniques, provide a synthetio approach for the synthesis of L-Phenylalanine starting fiom benayt chloride. {16 points) at :3 m fieu—m ‘fll C01 H e r m - - fl ,5 W x a a s-JG‘ r seem a." x w. __H.._,_.Hs 3 -——'.r we; ___- .-' I-r ." . \-* so tea. “a; ' ,. 4’ t soot ’"‘ F :17 .-- 1' 4' I 'f . U fix EM E ;L~iu- e ffifl [pr Healing"? .. "__- ..r' __. w J, I i F“ L x: ‘9‘“— \ w 3?" r “w rst’ie 3: ff {Aged r .-—. ‘- 1Irlll.|'—‘rlw_'_.i a at“... a I If -' k (“M i we / “r i :w 12):?"- “we 57} H C the” o r,“ s rrrh ? 3}- ? n A “r I if: s we? ' _e '2' «A . .1 a e ‘ ” be! Me A. i s .- 1‘ I ewe-‘2 * "MK “t! r, s ‘ 2.1 ., Haw i H .. 7 H N 3f“ H o r‘“ “' "F". *5“ ‘3 ‘" J h ‘5; A. " gds'fi’di "‘ I "1 {-1 ..~ - :___...“'- e h“ u IJI (/hfii-Ifdhr B) Propose a synthetic strategyr for each of the following reactions. Provide the mechanism, a1] reagents and possible intermediates needed for energyr reaction. Name the final products. {12 points) r© NH2 9 x e N: Es. *'~ o ,3 H“? V. to. '- .- ‘* tree-w . Got it's-s: : - ‘r.___:_<' "I—l fier- u I: K I.- x we xx” 1:; 3,.— ,\< I? I; ,x i I. ‘ 1 1 t ff“ t “"1 fl “_- /.h M. '1‘ : .-; ."'_'.' ‘1- l- r vs' : I N ‘-'::-:I.-- ‘\ u _ .fi- / $ P g a; JEFF-fl Iran" _ i n ;:p I: _l “_l ' . \mn‘ t H a. If a“; It a ,_ “ i' t H F Student Name: Problem 2 Provido tho major products for the following reactions. Pay attention to tho storooohontistry. [32 points) CH; O l H3 - 1W “H3 H IDMF I. :_ a} I E l-Ib -..L‘ I' .—'—h- hn..__‘ Ex N; Br ‘ “H: 2} NaoHaon-IF mgr H+IHzo L’r - 11' ooM NH . a 2 H » t ol —"I.:- F ___| I- b] Mao 3H no r rag ——-————-.-HL_H_IHJ‘_ D _ pyridine, DMF 1T) r; . _. _, KUH fr: . \K H _,.r c} I x —h' '“k m: 1'.“- N DMSD -. '1' ._.J T.- 1} NaNHE .'__I " I d} I '1; CH3 R F s —"" -. *3 2}oH3| :3] D O fax: 33 NHg-UHIH+ “AN .- I e] —i__ \_:fv_,!_.£3', Student. Name: Problem 3 :1] Draw cyclic Fisher projection, chair conformation and storth projoction for _‘__ 1 — - . A11: ' th cl'c four] of Altroso: 12 oints I“; a D: L Altopyranosc opyranoso 1s c o}; 1 _ “I! ( p ) Sf}? .....-=- , a.” i H.” CHO ___c . \. I: 1.35 : “fin—mix! I cw . . WW, H H ! ' low 1 4. 1.3 | ' .r .. i '5.”- . 1ft:- H OH H o~ .. ' 95:2-.. .. gm“... . H OH " i-i a i—f-nm L": ibis: j: H H I r E ’ _ '_ Li _ u . OH : ;>-- .".I TE I HQ"; Piling}; '~.\fi' ' Ll MALE fir. : i “fill .'::E__I' I i I I b) What Sugar or Sugars would rcsult from tho Kiliani—Fishcr Synthesis applied to D-Rihoso: {8 pints) Ho p . H W ' I. H 014 if '. .- -- .. .. :JIIIII'V-ra- ' ' 23-" s H UH .. :- H _ _ I .~- ,.-. y .~r_.- - -- CHzflrH Lara-v D—Ribose in!" ...- .= . _ __. |. ._._..—-—-- n - ' . - -" .._.-»— ""' : .- - 'P'F Problem 4 A} Complete the following reaetions: [12 points} Nil. Iti OH t .-':I t ,9 a) {GHacoizo / the; " ~ X “1,34 'r-AWHR pyridifltifi \ flflfif Elk/f?“ x b) HBn’aoetio aoiel ' '-'3‘“"""”"_ ‘3; my; ip ,4. gm (ooiel) ; .m — DH “ i Hoct i,-’-. ~ 3.3; i K+-S —<\_ f" i KI _ 3;;1‘ £114 .- q H RC “me-- “if “on 1}NaOH/i"i1i~? r; i it wi- ‘~ ’fl‘f‘k‘w ‘ 2}CH3-|, Excess I .. {I a: FF t: “2L: "‘— 5‘." \ I I _ ” 2}HCFIH2CJ ..-'”“*~....,‘-;,j;r; " -:- “W” B} Complete the following carbohydrate reaction (3 points). OH oH ' { HOE 1} NEOH. {CH3}2804 Student Home: uh- 'oH “DH I it: ...
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nefziMid2winter06 - Student Name: Problem I A] Using...

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