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Sodium amide is mainly used as a strong base in organic chemistry, often suspended (it is insoluble [7]) in liquid ammonia solution.One of the main advantages to the use of sodium amide is its relatively low nucleophilicity.
The mechanism above, loss of the hydride ion followed by abstraction of a proton, is supported by the fact that the nucleophile needs at least one hydrogen atom for the reaction to proceed. Another competing pathway could be the elimination of hydride by sodium to form sodium hydride.
However, it has the disadvantage to be prone to trigger unexpected and undesirable side reactions that can jeopardize the experimental results. Indeed, the azide anion is a nucleophile and a redox-active species. Being prone to disproportionation, it can behave both as an oxidizing and as a reducing agent. Therefore, it is susceptible to ...
A hydroxide ion acting as a nucleophile in an S N 2 reaction, converting a haloalkane into an alcohol. In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they ...
A nucleophilic aromatic substitution (S N Ar) is a substitution reaction in organic chemistry in which the nucleophile displaces a good leaving group, such as a halide, on an aromatic ring. Aromatic rings are usually nucleophilic, but some aromatic compounds do undergo nucleophilic substitution.
For example, in the S N 2 mechanism, a nucleophile attacks an organic compound containing the nucleofuge (the bromo group) which simultaneously breaks the bond with the nucleofuge. SN2 reaction of bromoethane with hydroxide ion
When a nucleophile adds to a conjugated carbonyl system, the result is a 1,4-addition. The designations 1,2 and 1,4 are derived from numbering the atoms of the starting compound where the oxygen is labeled “1” and each atom adjacent to the oxygen are sequentially numbered out to the site of nucleophilic addition.
In general, the reaction of a haloalkane with potassium hydroxide can compete with an S N 2 nucleophilic substitution reaction by OH − a strong, unhindered nucleophile. Alcohols are however generally minor products. Dehydrohalogenations often employ strong bases such as potassium tert-butoxide (K + [CH 3] 3 CO −).