Question

1. The following acidities of protonated oxygen-containing compounds have been measured. Provide an explanation for the widely varying results. M . + H+ N(Me)2 OCH3 pka 6 pka -9 pkg -7 pka -2.5 pka o 2. Using propyl iodide and carbon dioxide as the sole carbon-containing starting materials, outline a synthesis of propyl butanoate.

Answer 1

L OCAL Dreparation of propyl butanoate. Generation. CHOI: Grignard Reagent P9 (+ N, Helm Time NI propyl Iodide h-propyl Magnesium Iodide rection with cog, followed by Hydrolysis Step II: Reaction with n-butanoic cog, followe acido to tom ЛЛон n-butanoic acid. Step I: Fisher Esterification. Hell Nott Hon N ON + Hool nopropyl butanoate (esten no-propyl alcohol butancic acid . WOR