Aldol Reaction - Crossed-aldol Reactant Control

Crossed-aldol Reactant Control

The problem of "control" in the aldol addition is best demonstrated by an example. Consider the outcome of this hypothetical reaction:

In this reaction, two unsymmetrical ketones are being condensed using sodium ethoxide. The basicity of sodium ethoxide is such that it cannot fully deprotonate either of the ketones, but can produce small amounts of the sodium enolate of both ketones. This means that, in addition to being potential aldol electrophiles, both ketones may also act as nucleophiles via their sodium enolate. Two electrophiles and two nucleophiles, then, have potential to result in four possible products:

Thus, if one wishes to obtain only one of the cross-products, one must control which carbonyl becomes the nucleophilic enol/enolate and which remains in its electrophilic carbonyl form.

Read more about this topic:  Aldol Reaction

Other articles related to "control":

Aldol Reaction - Crossed-aldol Reactant Control - Order of Addition
... then add the other partner under kinetic control ... Kinetic control means that the forward aldol addition reaction must be significantly faster than the reverse retro-aldol reaction ... Common kinetic control conditions involve the formation of the enolate of a ketone with LDA at −78 °C, followed by the slow addition of an aldehyde ...

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