Editing Lithium diisopropylamide (section)

==Kinetic vs thermodynamic bases==
The deprotonation of carbon acids can proceed with either [[thermodynamic versus kinetic reaction control|kinetic or thermodynamic reaction control]]. Kinetic controlled deprotonation requires a base that is sterically hindered and strong enough to remove the proton irreversibly. For example, in the case of [[phenylacetone]], deprotonation can produce two different [[enolate]]s. LDA has been shown to deprotonate the methyl group, which is the kinetic course of the deprotonation. To ensure the production of the kinetic product, a slight excess (1.1 equiv) of lithium diisopropylamide is used, and the ketone is added to the base at –78&nbsp;°C. Because the ketone is quickly and quantitatively converted to the enolate and base is present in excess at all times, the ketone is unable to act as a proton shuttle to catalyze the gradual formation of the thermodynamic product. A weaker base such as an [[alkoxide]], which reversibly deprotonates the substrate, affords the more thermodynamically stable benzylic enolate. An alternative to the weaker base is to use a strong base which is present at a lower concentration than the ketone. For instance, with a [[slurry]] of [[sodium hydride]] in THF or [[dimethylformamide]] (DMF), the base only reacts at the solution–solid interface. A ketone molecule might be deprotonated at the ''kinetic'' site. This [[enolate]] may then encounter other [[ketone]]s and the thermodynamic enolate will form through the exchange of protons, even in an [[aprotic solvent]] which does not contain hydronium ions.

LDA can, however, act as a [[nucleophile]] under certain conditions.