Devise the most efficient synthesis for the carboxylic acid below using a starting material and reagents from the tables. Give your route by specifying the number of the starting material followed by the letters of the reagents you would use beginning with the first step. The answer 4fh means treat t-butanol(4) with conc. HCl(f) then treat the product with KOH in alcohol(h).
OH Starting materials Br Br OH H3C 2 OH Reagents a Mg /dry ether e Aqueous H2SO4 at reflux i KMnO4 /H3o b 1. CO2 2. acidic workup f Conc. HCI or HCI (gas) j Na2 CrOs /aqueous H2SO4 c NaCN / THF or DMF g PBr3 k 1. BH/THF 2. H,Oz/aq, NaOH h KOH I alcohol d NaCN / dil. aqueous H2SO4
