1would you xpect the alpha-protons of a thioester to have a, Ask an Expert

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1.Would you xpect the α-protons of a thioester to have a lower or higher pKa than an ester? Why? Remember the pKa values for the α-protons of several FG's: aldehyde(17), ketone(21), ester(25), amide(35).

2. Would you expect a thioester to be more or less reactive toward an acul transfer addition elimination reaction than an ester? Why or Why not? Propose a short synthesis of a thioester from the corresponding carboxylic acid, and draw the mechanism of the reaction which forms the new C-S bond.

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