For instance conversion of the ketone to an alcohol by lithium aluminium hydride can be considered a reduction but the hydride is also a good nucleophile in nucleophilic substitution.
32.
Sodium ethoxide may either deprotonate the ?-position of an ester molecule, forming an enolate, or the ester molecule may undergo a nucleophilic substitution called transesterification.
33.
In general, the reaction of haloalkane with potassium hydroxide can compete with an S N 2 nucleophilic substitution reaction by OH " a strong, unhindered nucleophile.
34.
Mechanistically, the reaction proceeds with potassium hydroxide deprotonating a methyl group and the resulting carbanion undergoing nucleophilic substitution with methyl iodide to form a new carbon carbon bond.
35.
Many nucleophilic substitutions occur more easily not with bare pyridine but with pyridine modified with bromine, chlorine, fluorine, or sulfonic acid fragments that then become a leaving group.
36.
For example, kinetic isotope effects can be used to reveal whether a nucleophilic substitution reaction follows a unimolecular ( S N 1 ) or bimolecular ( S N 2 ) pathway.
37.
For the aforementioned nucleophilic substitution reactions, secondary hydrogen kinetic isotope effects at the ?-carbon provide a direct means to distinguish between S N 1 and S N 2 reactions.
38.
Amines may also be prepared from alkyl halides in amine alkylation, the Gabriel synthesis and Delepine reaction, by undergoing nucleophilic substitution with potassium phthalimide or hexamine respectively, followed by hydrolysis.
39.
Studies show that DPPA reacts with amines giving the corresponding phosphoramidates; it therefore appears that formation of the amide similarly involves the intermediate anhydride, followed by nucleophilic substitution by the amine.
40.
However, reacting with potassium hydroxide would compete with an S N 2 nucleophilic substitution reaction ( minor product ) because OH "-ion is a strong, sterically unhindered nucleophile.
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