The flavor of beer can be tainted by a trace contaminant, called ortho-bromophenol. To reduce the incidents of contamination, beer manufacturers have used certified beer flavor standards to train professional beer tasters to recognize the flavor of ortho-bromophenol. Preparing these certified standards requires pure samples of ortho-bromophenol. Propose a synthesis of ortho-bromophenol starting from phenol. (Org. Synth. 1934, 14, 14.) In a reaction, a reactant with the SMILES string Oc11 yields a product that has the SMILES string Oc11Br. Choose from the reagents below. To record your answer, place the appropriate letter in each box below. Enter only one letter in each box. Each reagent can be used more than once. a) dilute NaOH
b) Br2, FeBr3
c) HNO3
d) conc. fuming, 1 mol H2SO4
e) Zn
f) HCl
g) HBr
h) Dilute H2SO4
i) Br2