Q1Key_Wi03 - NU Winter 2003 2 1(20 pts Complete each of the...

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Unformatted text preview: NU, Winter 2003 . 2 1. (20 pts) 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. To 9C1”; : $0. M f3 . 4?“! OH EKH H2834 ’jké Eoss dHu) ) 4- WW 4w 7w a @ .,.-> 7‘46 ~——3/iL(‘ 1) mCPBA (a peracid) /0 / m 4913 ii. V\ 3) PCC / 950 :< 0 MI» W 4 (“9 iii. 1) (ya. u Nor {L 3 K 1) Ko‘Bu, heat 3 (“k or). 2) 3H3, THF OH w‘wc fox/<7 act-7:; 3) H202. NaOH / P,» P :L Gm Time—2 (reps 7F use 6 2) 8% J 2) Pcc, #3 v 3) meat: 9 “We" M we 4.) Rd) F} S) LAZGR 2. (10 pts) Propose a mechanism for the following reaction using the curved arrow formalism. Provide 4‘11; iv. all proton transfer steps. 0 /\OH + 0—st ___._> /\C| + 8,:0 + HCI .t¥/ Cl \ W ? 69 O t o [4) gpfi Q) (l 4% M» g\ CQ, NU, Winter 2003 , 3 3. (20 pts). Propose a synthesis of the following compound from propene as the only carbon— containing starting material using only the reactions that you learned in Chem 210-1. You may used any necessary inorganic reagents and any sulfur-containing reagent. “WWW *n‘L huh”; ,3 Cl 014 multistep synthesis ( ,_,> A a” §O L 24¢. 24¢; \J/ l E“; ‘W PC C q. 2/)HLOL)5-H ‘ ) 1 6x 2, L430 M» /E La All j/ um? 2’“ //\~————9 Olk 1 etc, 21“: w 3» N Z //\ W PK”; /\IJ/< A79 1) awe; at NM?) a) 1450* me or LI"; Ur ...
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