Breaking an ester linkage can proceed by different bonds and mechanisms. Acyl–oxygen and alkyl–oxygen cleavage should be distinguished when explaining protecting-group selectivity.
Breaking the bond between an acyl carbon and the ester alkoxy oxygen. Ordinary hydroxide-promoted ester saponification follows addition–elimination through a tetrahedral intermediate.
Breaking the bond between an ester oxygen and its alkyl substituent. Acid removal of a tert-butyl group can follow this route without requiring water or a tetrahedral acyl-addition intermediate.
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