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Q1Key_Wi05 - NU Winter 2005 Quiz 1 2 l(20 pts For i gives...

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Unformatted text preview: NU, Winter 2005, Quiz 1 2 l. (20 pts) For i, gives the IUPAC names of the structure shown. For ii-v, complete each of the following reactions by providing the missing starting materials, reagent set(s), or product (only the carbon-containing major product is necessary). If a reaction does not occur, please state so. Your answers should be consistent with any stereochemistry that the reaction may require. OH Tl 1 “C4"M‘Zrlfdmw @ 2— l“Mn—Z”%r dew M L (1/ C46 \——l 1) 0.01 s, 1500°C ( “ ' “ 2) Lindlar's catalyst, H2 2 CH4 .. -——— ' ,, L wx. t“ 9 «A. ( \ 405 p Z) “0/ NH}, 3 A (Cgimi‘h: 3 AW iii. g} Prw B» l ' ‘ o 4,) KMKO4. ) Agwfi-L 1) LiCu(CHZCECCH3)2 2) excess 03, excess H20 0 O 4 i“; “3 ~—\& (: I HOWOH + 2 /U\OH (”M/- iv. F‘:°/\\ O /, 0:"; 0 L3 {3 all) I+Lt( If.) OMe S) O; 04 ) H) 0” /L7/O\/ Av lbw , V x, ( (a ' AM E— 1.:‘_\—,W .‘ A/Ov 6) NW” (lg/*2) ) V 3) NaOFfié (l quW)( #200] 0M8 ‘31 ) M? (an. at»! 4.) Kate» JA , (M...:15'/\ ) 2. (10 pts) Propose a mechanism for the following reaction using the curved arrow formalism. Provide all proton transfer steps. Hint: KO’Bu is a bulky strong base 0 KOtBu catalyst 0H Ll OH AJflK DMSO (a very polar solvent) a + V El heat NU, Winter 2005, Quiz 1 3 3. (20 pts). Propose a synthesis of the following compound from ethyng as the only carbon—containing starting material using only the reactions that you learned in Chem 210-1 and the last two weeks. You may use any necessary inorganic reagents, mCPBA, and any sulfur—containing reagent. 9 0, OEt 01 M .< ¢> ALI/‘V’f nga OEt go 4 w .: 3L (fem % U ’ at W ll OH 2’: 21.1: (NatWUq, S? l t N‘ \/ “£6;ng em w o (J ‘ Wt ace/we cum 91w“: W chm 2"“ We ai @ tut u \ ll CW3 "2 ”£02 ) \xm/fl/M 2P1; \LWQMJHL Ajg ...
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