Chapter 14 Worksheet 031)2)3)4)Reactions : Please provide the starting material, reagents or product(s). Indicate stereochemistry where applicable.www.ochemweb.comOOHO1) CH3MgBr (excess)2) Na2Cr2O7/H2SO4/H2OOHBrOHC CCH3CH2CH2CH3CH3CH3CH2H Br1) CH3O- Na+ / CH3OH2) MCPBA / CCl46)7)8)9)www.ochemweb.com5)BrOHNHOOOHin CCl4CCH3CCH3HHBrCH31) 2) 3) HClBrBrBrMgBrOHOHOwww.ochemweb.com10)11)12)OLi+2) H3O+OHOHOHOHCircle the major product formed by the following reaction sequence:13)HOOOH1) H2SO4 / heat2) O33) DMSOHOH1) O32) (CH3)2S3) NaBH4/EtOHwww.ochemweb.com14)15)OO1) CH3CH2MgBr2) H+OOOO1) LiAlH4(xs)/Et2O2) H3O+1) CH3MgBr (excess) / Ether2) H3O+DOH1) PBr32) CH3O- Na+ / CH3OH16)17)OHOHOH18)19)20)21)www.ochemweb.comBrBrOHOCH3OCH31) 2) Na ( 2 eq)3) CH3I ( 2 eq)ONaBH4/EtOH+What's the relationship between the two products?Br22)23)24)www.ochemweb.comOHBrOHOHBr BrCH3CH2S- Na+ (2 eq.) /
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