mid1 - 1. (24 pts). Draw the structure of the expected...

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Unformatted text preview: 1. (24 pts). Draw the structure of the expected organic product(s) formed in the following reactions. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. 0 1) BngEt, ether A ) fi/KOCHQCHs 2) H2804, H20 M H20, 20 00 B) NH 2 O 1) LDA, THF, -78 0C c) M OEt . 2) (CH3)ZCHCHZCI O D) O O /U\S—Protein V Hows-Protein O E) P (cat), Br2 (excess) We CEN 1)MeMgBr, THF F) —( 2) H30+, H20 Enzyme 2. (20 pts.). Show detailed reaction mechanisms for each of the following reactions. I Include the structure of the expected products. RJ‘d soot2 lyf o 9 o F / c r _ a- v ’ ‘1‘qu +2420 "WV , RJCEQ-FBK ’ M) E‘N? r4. 4' rzfi’ >H/Q\H rs» I V3 ‘ ‘ v r v C/ggv’, —-——-;P R “N? Hi 6"“ R NHL 4’ M w W H’ 3 5” Pf it Wr ’ 3. (22 pts) Show how you would carry out the following synthesis. Include the ‘ ' reagents you would need for each step and the structure of the intermediate products formed in each step. A) R \/\/OH o . . 7 , Eff \l/ seal/M Wr w, ng/iogc/ojaa “5+ R Cl \y- ' '7 R /N/‘ \/\\G( \z— B) R/YOCH3 R/\/fi\/k ’bLEH few,» 2p}; TQNQZC—‘xliiiélilé *1/13H30‘L/HZQ lfl’l ‘ i K-CHZ’CHZ’CH R~CHL’CH2C‘CI x) 5GC11 2N3 the, my ' DKUWDMF’ 19”? C 4. (8 pts). Rank the following compounds in decreasing order of acidity. l 0 0H Canal“ 0 O O o o o o FSC/U\OH CIHZC’U\.OH Hac’lLH Hsc/lLOH Hac/lLN(CH3)2 Ho'gfo“ Clac’U‘OH 5 7 CI A B C D E F ‘ G H F>A>e~>B>H>D, >C >1: Highly Acidic Moderately Acidic Poorly Acidic 5. (6 pts.) Provide the systematic names of each of the following compounds. “MP/s Peach 0 , . I t A) C! z'melLVI *L/‘Fheny'l bvl‘cmo Y] CM lo HOG. O B) NN/ N,N~0limel’l\// h€><4h0xhq70€z O C) I:3C/U\OCH3 i we re (Mel;ng . 0 r ‘ NEW! l)“; give/*0 Gfiio, “0% 5 v (20 pts.) The unknown compound A (C14H21N02) gives the following proton and caflxn1bfl~flispect2LSignificantflklmmksvwmczflso(flxxxved.IkxhnnknlofIXVvfih > LiA1H4 gives compound B (CHHuNOz). Reduction of A with DIBAL give compound C (C10H1202)- , ' 1H ’2H 200 150 100 50 . 0 IR: 1) 3010, 2950, 1670 cm'l. A ++ ~ «P ,ykemlvgpk ...
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This note was uploaded on 05/08/2008 for the course CHEM 118C taught by Professor Xichen during the Fall '08 term at UC Davis.

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mid1 - 1. (24 pts). Draw the structure of the expected...

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