Enolate alkylation involves the reaction of an enolate ion with an alkyl halide to form a new carbon-carbon bond. The nature of the alkyl halide greatly impacts the reaction’s outcome due to factors like reactivity and sterics.
Primary alkyl halides typically undergo SN2 reactions with enolates, leading to straightforward alkylation.
Secondary alkyl halides may also react via an SN2 mechanism, though they can be hindered by steric effects, which can slow down or prevent the reaction.
Tertiary alkyl halides are usually too hindered for SN2 reactions and can instead react through an SN1 mechanism or not at all, potentially leading to side reactions, such as eliminations or rearrangements.
The choice of alkyl halide is, therefore, crucial for achieving the desired alkylation product.