The requirement for a good leaving group is relaxed in conjugate base elimination reactions. These reactions include loss of a leaving group in the β position of an enolate as well as the regeneration of a carbonyl group from the tetrahedral intermediate in nucleophilic acyl substitution. Under forcing conditions, even amides can be made to undergo basic hydrolysis, a process that involves the expulsion of an extremely poor leaving group, RN. Even more dramatic, decarboxylation of benzoate anions can occur by heating with copper or CuO, involving the loss of an aryl anion. This reaction is facilitated by the fact that the leaving group is most likely an arylcopper compound rather than the much more basic alkali metal salt.
This dramatic departure from normal leaving group requirements occurs mostly in the realm of C=O double bond formation where formation of the very strong C=O double bond can drive otherwise unfavorable reactions forward. The requirement for a good leaving group is still relaxed in the case of C=C bond formation via E1cB mechanisms, but because of the relative weakness of the C=C double bond, the reaction still exhibits some leaving group sensitivity. Notably, changing the leaving groups identity (and willingness to leave) can change the nature of the mechanism in elimination reactions. With poor leaving groups, the E1cB mechanism is favored, but as the leaving groups ability changes, the reaction shifts from having a rate determining loss of leaving group from carbanionic intermediate B via TS BC through having a rate determining deprotonation step via TS AB (not pictured) to a concerted E2 elimination. In the latter situation, the leaving group X has become good enough that the former transition state connecting intermediates B and C has become lower in energy than B, which is no longer a stationary point on the potential energy surface for the reaction. Because only one transition state connects starting material A and product C, the reaction is now concerted (albeit very asynchronous in the pictured case) due to the increase in leaving group ability of X.