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[Review Topics] Devise the most efficient synthesis forthe carboxylic acid below using a starting material and reagents from the tables. Give your route by specifing 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. HCIf then treat the product with KOH in alcohol(h). Starting materials OH OH Br OH Reagents a Mg dry ether e Ethanol, Haso4 (trace) at reflux i OSO b 1. CO2 2. acidic workup f Conc HCI j Na2 CrO4 l aqueous H2SO4 c NaCN /THF or DMF g Her k 1. BH3THF 2. H202 aq, NaOH d NaCN/dil, aqueous H2SOs h KOH /alcohol

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The product can be preapred using the following reagents. j. Na CrO4 Aqueous H,SO4 он он Br Br

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