Sciencemadness Discussion Board

Question about base catalyzed transesterification mechanism & isomerization.

RareEarth - 13-8-2015 at 02:09

Say I have a compound with two carboxylic groups on it, and both are esters, but with different alcohols. Would a base catalyzed transesterification (to isomerize) cause the alcohol groups present at each ester to swap around and become jumbled? Or does the transesterification only work if there are free-nucleophiles in the solution to attack?

I read that for the transesterification to happen, an akloxide needs to form between the base and free alcohol first? I guess my question is can another deprotonated ester behave in this similar manner and effect transesterification?

[Edited on 13-8-2015 by RareEarth]