Final_Wi02 - NU Chem 210-2 Winter 2002 Final exam 2 1(24...

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NU Chem 210-2, Winter 2002 Final exam 2 1. (24 pts) Complete the following reactions, be careful to give all the major carbon-containing products, starting materials, or reagents. Clearly indicate the stereochemistry when relevant. If there is no reaction, say so. a) Br OO b) O O c) O 2 N O OH d) 1) 1 CH 3 Br, FeBr 3 cat. 2) KMnO 4 hot, conc. 3) CH 2 N 2 e) 1) 2 PhMgBr 2) H 3 O + , H 2 O 3) Ph 3 P=C(H)Ph 4) H 3 O + , H 2 O O HO f) 1) Cl 2 , AlCl 3 cat. 2) KOH fused, 3) Br 2 4) KO t Bu excess, heat
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NU Chem 210-2, Winter 2002 Final exam 3 2. (24 pts) Complete the following reactions, be careful to give all the major carbon-containing products, starting materials, or reagents. Clearly indicate the stereochemistry when relevant. If there is no reaction, say so. a) Br OO H O H b) 1) CH 3 C(O)Br, FeBr 3 cat. 2) NaCr 2 O 7 , H 2 SO 4 , heat 3) SOCl 2 4) LiAl(O t Bu) 3 H c) 1) NaH 2) CO 2 3) H 3 O + , H 2 O 4) CH 3 C(O)Cl, AlCl 3 excess, heat 5) BH 3 •THF OH d) OH OMe NH 2 I I e) H OH f) 1) Na (excess), NH 3 (liq), -78 o C EtOH 2) H 3 O + , H 2 O 3) O 3 (excess), Me 2 S (excess) 4) NaH 5) MeNH 2 (excess), H 3 O + cat 6) LAH (excess) 7) H 3 O + , H 2 O O HO
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NU Chem 210-2, Winter 2002 Final exam 4 3. (20 pts) The Wittig reaction is quite useful in the conversion of an carbonyl compound into an olefin. In one special case, the Wittig reagent Ph 3 P=C(H)OMe can be used to convert a carbonyl
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Final_Wi02 - NU Chem 210-2 Winter 2002 Final exam 2 1(24...

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