Chapter 14 Worksheet 02 Reactions Please provide the starting material reagents or product s Indicate stereochemistry where applicable 1 1 Br N OH 2 HI xs 2 H3O O 2 OH CH3 CH3O CH3OH H 3 O CH3OH H O 4 O Br Br Br Br 5 www ochemweb com CH3 6 O 1 CH3S Na 2 H3O 1 NaNH2 150 C Br Br 7 CH2 CH CH CH3 2 H 3 Sia2BH 4 H2O2 OH 5 H3C C C 6 H Br OH 8 OH OTos 9 1 CH3 3CO K 2 O3 3 DMS Dimethyl Sulfide 4 NaBH4 EtOH OH CN 10 CH3 CH3 www ochemweb com 11 O O 12 H H HO CN H NC H 13 O 14 15 O HBr xs CH3 CH2 OCHCH3 CH3 www ochemweb com O 16 CH3 17 H3C C O CH2 CH3 18 O 19 D 1 Hg OAc 2 CH3OH 2 NaBH4 CH3 20 O www ochemweb com 21 Br 1 CH3 3CO K 2 MCPBA 3 CH3MgBr 4 H3O 1 NaNH2 150 C Br Br 22 O 2 H3C CH CH CH3 3 H 23 1 Br2 H2O 2 NaOH 3 MgBr 4 H3O 1 Hg OAc 2 H2O 2 NaBH4 24 3 Conc H2SO4 heat 4 MCPBA 5 CH3CH2OH H 1 BH3 THF 25 2 H2O2 OH 3 PBr3 4 O 5 HI xs www ochemweb com 1 BH3 THF 26 2 H2O2 OH 3 Conc H2SO4 4 MCPBA 5 HCl O 27 CN 28 29 O www ochemweb com OH O 30 H H H3C OH H3C H H3C OH Hint Look for change in stereochemistry OH www ochemweb com
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