Question

9. Give answers for each part of the question in the space provided. Give the major organic product(s), the starting material (reactant), or the reagent(s) as indicated in the synthetic transformations below. If two or more products form in approximately equal amounts, draw structures of both. Indicate stereochemistry where appropriate. Cl2 CCl4 NaoMe Br Me MeOH ~ 1. B2H6 2. H2O2, NaOH 1.KMnO4, NaOH, heat 2. H3O+ Br

Answer 1

C12 Cl + ccly antiadditim Naome -7 MeOH me E 2 elimination `아H -7 2 102,N9DH Hadooboration oxidetion OH at loss Substituted site 1-kM noy, Nao heat 2. H3C + HO Oxidative-clravage 1Bry,HzO anti ad itian of 1. OsOu 2. Ne H S03 cis -diol kotBu t-1300H E 2 eliminatin