_:nc52e785faeb74740ba6e93c49ddf5cf9xb27
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"<p>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&rsquo;s outcome due to factors like reactivity and sterics.</p>\r\n\r\n<ul>\r\n\t<li>Primary alkyl halides typically undergo S<sub>N</sub>2 reactions with enolates, leading to straightforward alkylation.</li>\r\n\t<li>Secondary alkyl halides may also react via an S<sub>N</sub>2 mechanism, though they can be hindered by steric effects, which can slow down or prevent the reaction.</li>\r\n\t<li>Tertiary alkyl halides are usually too hindered for S<sub>N</sub>2 reactions and can instead react through an S<sub>N</sub>1 mechanism or not at all, potentially leading to side reactions, such as eliminations or rearrangements.</li>\r\n</ul>\r\n\r\n<p>The choice of alkyl halide is, therefore, crucial for achieving the desired alkylation product.&nbsp;</p>"
<https://chemistry.coach/organic-chemistry-3/enols-enolates-and-aldol-condensation>