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). a Mg/dry ether b 1. CO_2 2. Acidic workup c NaCN/THF or DMF d NaCN/dil. Aqueous H_2SO_4 e Ethanol, H_2SO_4(trace) at reflux f Conc. HCl g HBr h KOH/alcohol i OsO_4 j Na_2 CrO_4/aqueous H_2SO_4 k 1. BH_3/THF 2. H_2O_2/aq. NaOH l.

Explanation / Answer

7 - g - a - b (Or) 7gab

BrCH2CH2CH2CH2OH +HBr ---> BrCH2CH2CH2CH2Br --2 eq. Mg/dryether --> BrMgCH2CH2CH2CH2MgBr ----2 eq. CO2/Acidic workup----> HOOCCH2CH2CH2CH2COOH

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