2.5. Enol and Enolate Reactions Preamble

The reactivity of enols and enolates as nucleophiles is incredibly complex and has a very long history. Many institutions have entire courses devoted to this specific subsection of organic chemistry. In practice, specific details (the exact metal cation of the enolate, the exact solvent(s) used, the presence of salt or metal additives, etc.) affect problematic properties of the reaction (complexation, the nucleophilicity of the oxygen, the E/Z stereochemistry of the alkene in the enol(ate), etc.) which can have drastic effects on the product(s) formed. At an introductory level these considerations are omitted; the goal is to understand the basics and the reactivity pattern of enols/enolates as nucleophiles in general. However, it is important to be aware these reactions are more complicated as additional details may be encountered in some sources.