CHEM 346 PROBLEM SET 2 Due 2 2 12 Please complete the following problems You may work either in groups or on your own The answer key will be posted on RamCT on the due date 1 Bruice Ch 16 problems 13 17 20 ignore c 45 51 60 2 Predict product s for the following reactions Br Cl O H3C CH3 H3C CH3 O Cl AlCl3 HNO3 H2SO4 Br2 FeBr3 Cl AlCl3 A B C D E F G H CH3 Cl HNO3 H2SO4 OCH3 NO2 BF4 CH3 NO2 BF4 H3C H3C H3C CH3 NO2 NO2 OH Br2 AlBr3 3 The following compound was treated with bromine to accomplish a monobromination Based on your understanding of the mechanism of bromination and the influential nature of substituents on aromatic rings identify the four potential sites of bromine atom substitution and determine which of the four would be LEAST likely to be brominated H HO O H H Br2 OCH3 4 Design synthetic sequences for the following transformations from the illustrated starting material A N from Br HO from Cl O Cl B
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