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.?

?? Starting materials Br ?? ?? 4 ?? Br 6 Reagents i KMnO4/Hy0 i Na2 CrOs/ aqueous H2SO k 1. BHy/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 9 PBr3 d NaCN / dil. aqueous H2SO h KOH/ alcohol

Explanation / Answer

Route 1:

8.1-octene, f. Con. HCl, c. NaCN, THF e. Aqueous H2SO4, reflux

Route 2:

8. 1-octene, f. Con. HCl, a,. Mg, ether, b. CO2, acidic work up

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