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.

Choose from the reagents below. Each reagent can be used more than once.

a) dilute NaOH

b) conc. fuming, 1 mol H2S04

c) Zn

d) HBr

e) HCl

f) Dilute H2S04

g) Br2

h) Br2, Febr3

i) HNO3