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

ID: 764614 • Letter: D

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. HCI(f)then treat the product with KOH in alcohol(h). Starting materials Reagents Mg /dry ether 1. CO2 acidic workup NaCN/THF or DMF NaCN / dil. aqueous H2SO4 Ethanol. H2SO4(trace) at reflux Conc. HCI HBr KOH/alcohol OsO4 Na2 CrO4 / aqueous H2SO4 BH3/THF H2O2/aq. NaOH

Explanation / Answer

6gab g --> give alkyl halide a ---> give Grignard b ---> give RCOOH product with one more carbon.

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