Extent of proton transfer variations

Atom Variations E2 Heteroatom Variants, Dehalogenation, Fragmentation Vinylogous Variations Sn2 and E2. 1,4 additions Extent of Proton Transfer Variations General Acid and General Base Catalysis of Additions and Eliminations, Summary by Media, Push-Pull Catalysis of Enolization... 

Energetics, utilize the rule. The anion formed must usually be more stable than the Nu or the reaction will reverse by path Ep, the microscopic reverse of this path. However, in a protic solvent the initially formed anion may be rapidly and irreversibly protonated before the reverse reaction can occur. In acidic media, protonation of Y can also occur prior to or simultaneous with nucleophilic attack (see Section 7.4.3, Extent of Proton Transfer Variations). 

Figure 10.14 Amide hydrolysis overview. The most likely reaction path is boxed. Additional paths that invoke extent of proton transfer variations like general acid and general base catalysis are also possible (Section 7.4.3).

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