Devise the most efficient synthesis for the carboxylic acid below using a starti

Question

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 OH 2 4 OH 6 Reagents i KMnO4/H3O j Na2 CrO4 / aqueous H2SO4 k 1. BH3/THF 2. H202/aq. NaOH a Mg / dry ether e Aqueous H2SO4 at reflux b 1. CO2 2. acidic workup f Conc. HCI or HCI (gas) c NaCN/THF or DMF g PBr3 d NaCN /dil. aqueous H2SO h KOH/alcohol PreviousS Next

Explanation / Answer

answer is 8i

KMnO4 can oxidise the alkenes to corresponding carboxylic acid

you can get some examples from this link

http://askthenerd.com/ocol/CH19/F2.HTM

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