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Date: 21-12-2015
7233
Date: 22-10-2020
789
Date: 9-9-2019
399
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Enolates can act as a nucleophile in SN2 type reactions. Overall an α hydrogen is replaced with an alkyl group. This reaction is one of the more important for enolates because a carbon-carbon bond is formed. These alkylations are affected by the same limitations as SN2 reactions previously discussed. A good leaving group, X= chloride, bromide, iodide, tosylate, should be used. Also, secondary and tertiary leaving groups should not be used because of poor reactivity and possible competition with elimination reactions. Lastly, it is important to use a strong base, such as LDA or sodium amide, for this reaction. Using a weaker base such as hydroxide or an alkoxide leaves the possibility of multiple alkylation’s occurring.
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