Final-Key-140C-winter-2006

Final-Key-140C-winter-2006 - Student Name: Problem 1 What...

Info iconThis preview shows pages 1–8. Sign up to view the full content.

View Full Document Right Arrow Icon
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 2
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 4
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 6
Background image of page 7

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 8
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Student Name: Problem 1 What are the stmctures ofcompounds A, B, C, D, E and F, for the following reactions. {DI-THE: 2,4—dinitrofluorobenzene]. (24 points} a) 5H Hi 1} DNFE {excess} HZNEJiNLn’N: DH H—I-r A + B + c = H o = 0 2m” Hcl.2ou °C,mrernight NH2 hlddult Ham: Sunni-.5. I'rrmt pfihfilf'ffl'llfl nmthyl able-rid: trap-EL. and abang 13h; «ppm-mime [Eviutlkfl .zm'nn :ufiilia-L rL—ugenizi and Imihni'qlzus. pnu-ific u 5311:1121 In: appmai‘h ['m flw wlid plum: fimlhesis urn“: Inflow,ng cumpnamr}: { I'hc: :wurnliilinn, um auhclinnmi a! 1"“: punilinn 2 1'5 Hiflhic’ In IE1: «lawn-nim- :1m111iti:'.n:~:nf !hc rosin}. i_l‘.fi {atrium Li a DH 0 .. H \l\/“ Ac.- IH"; €314 Ii} 30“ ma 2. Ext aim-helline maiflmmw fl. . Fin-H ,. _ a —I:' .-:.I__ ‘ £13."? .' - 'fill 11 ll ' " H h. _. L — a. _ . _ _ N ..r . _ 55H 3'" __ a - ¢ _ — II- 1 I . 1. '- '| ' .. I.- ~“- ’2’ Iain-5:1, ‘- Lz'n— I i J .. ' F. _ n H __ __ :L : n '_,, . I -. H I' _ . I _ i- , 1 _ i r i E I x . . x _ I _ mg" " ~ _ I . ;5 {1| . '1 _ if: I s". _ . I - '- -" Hug.- H” I: - r--" _ J _,II. I F".- 1- _ ‘ . J. .r'. . I m I I _ I __ -. “a; 4.. 'HI I I t I __..-' d _ _,T '\ --—-. H' in-.. ifi’fl‘Hf- [13%. “a”! r .- | \_ I -. w. ".I i. _.¢ .1- - 'l .|.' . s_ i. a _.3' Problem 3 Student Name: The exaselidine ring derived from serine is used as pseude-preline to facilitate peptide synthesis. Using Streeker synthesis and appropriate reagents and techniques, provide a synthetic appraaeh fer the synthesis of Fines protected axazelidine fiem 2-benzylexyefl1anol. stereeehemistry). {25 paints] DeessrflH Z-Benzylexy-ethanel if /" FCC.” a"? kw/L‘O fixtwa D 1 . i HCJH ~Ji5 ! | |. W NHL [57"; nghi Nu“ m J i ,. ' xv; "IM. 5'“ E x “I”! “Hi ' 9 {‘U a??? —————————n. {Pa}.r attention to the O ><JIN 0H Fm ee 0 Student Name: Problem 4 Propose synthetic strategies for the following reactions. Provide all neeessarj.r reagents and show all intermediates. {24 points) D a) _. é Mimi/“230$ L) two/Hoe N3; LM‘LMHfi h a} and}; use 4" LtQHtt’tet ‘ H'TH :1 ML 2’) g) cm (ll/ :1ng k H Ch? £45” I": CH5: ERR}, / “a a; w; (n —-—=:~— \ Student Name: Problem 5 For the following reactions, give the complete structures of the compounds presented by letters. [36 points] a) a a J11 H e H N SH 3)=o j\flJLo/1LOJ< 2 i 0” % RH L... A a —-—-——-—-—r-- c + D + E E? a reflux DIEA,DMF ole.oMF s >< H S 3 / ,oH _ A: @ C _ XMXr/MUE/Hxfl I L). 74 l PK If New.“ N b} ,0 .0 1 NH In EMF 1] LiAIH-I- In THF "‘ < : snob, 2H2!) c. CN'ICUBM 2] HHHED A —-—-——h- —h- B —I-- D —p- -—p- E 2} NaBchN DMF DMF amen-He :nhydride. othero "02 N DIENDMF “9e” O f 1 J a. NJL. 16} ED H; 5—, E} E: Student Name: Pruhlem I5 ‘ 1 What is tha major product fiat each 01‘ the following reacimna? Don’t pay attenuun to the $Lere0chernistry. {36 points) K Nath INH / HNGzJH2504 5’ H K; a l _2:.. (I _. —.. a» \L _. N HN/ “Hi n \ 0 X \n’ “NH: un— ~\ 11TFMDCM \ +— \ /’ W O K N a 21 DIENDCMD ,T J a DMF l 3}®_4< N H J N” Em DIEAI Dcfil \L/ n H N 1} LDAITHF —< H2 NH2 in nu": '< j C§=U —* L '4’ —I-‘ /<M 21:3H5-6H25r in Dmso r H 6) :31 _ 1} 03 2? NH 1] CHg-l excess m DMF L 2:51:02, NaDHIHZD, H+ i? 2 ——:a.. —:-- x 2] A920, H20, heat I 3] Bra. tracers of P Br DH 0 fl 1} LiAIHJI‘HF F C“; .— 5 L1 CHSCHZOH fH“ / Marx {Excess} \[/ —p-h -—.I- 0 heat [\ H‘jlr’gw” 2} HflHzo fl (1143 5H 0 . £3 1} Mg I Ether 1 Br 2}coer*ero 1]NH3 in DMF C>_/ L —-—--—II'- . 21 Brz, NaoHn-Izn 3} SOCIz, DOM, DIEA Student Name: Problem 7" Complete the fellewing reactions. [35 points} :3 Cl H+.I'H D \fu‘eH —-iI- '0 It DH 1 Q 2 equivalents //\"" H! J / ‘~ M H W0“ 3 a I MN,“ HO “"+ u 11LIAIH4nHF / ——+ o 1/ a 21:4?ng M L) 31 Nam-nae” '1 :27 & D Hill, EtflH, heat I KCH; _.— T MIL/Ea + Hze=o + H“ —3... D M Br _ . i" o g H 2] H” H20 H . .3 C) 1} Eta-NattEteH ) k H a DA 2: H+ !' t/ £1 E: D I 1+ t.» \r; _\ (.4 ...
View Full Document

This note was uploaded on 04/07/2008 for the course CHEM 140C taught by Professor Nefzi during the Spring '06 term at UCSD.

Page1 / 8

Final-Key-140C-winter-2006 - Student Name: Problem 1 What...

This preview shows document pages 1 - 8. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online