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Carboxylate ions are good nucleophiles. They react with alkyl halides to form esters. The following reaction shows the reaction mechanism. [1]: 398–9 The S N 2 reaction between sodium acetate and bromoethane. The products are ethyl acetate and sodium bromide.
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 ...
While nucleophilic acyl substitution reactions can be base-catalyzed, the reaction will not occur if the leaving group is a stronger base than the nucleophile (i.e. the leaving group must have a higher pK a than the nucleophile). Unlike acid-catalyzed processes, both the nucleophile and the leaving group exist as anions under basic conditions.
The requirement for a good leaving group is still relaxed in the case of C=C bond formation via E1cB mechanisms, but because of the relative weakness of the C=C double bond, the reaction still exhibits some leaving group sensitivity. Notably, changing the leaving group's identity (and willingness to leave) can change the nature of the mechanism ...
A variety of nucleophiles attack, breaking the carbon-oxygen double bond, and leading to addition-elimination reactions. Nucleophiliic reactivity is often proportional to the basicity of the nucleophile and as nucleophilicity increases, the stability within a carbonyl compound decreases. [5]
Converting a carboxylic acid to an amide is possible, but not straightforward. Instead of acting as a nucleophile, an amine will react as a base in the presence of a carboxylic acid to give the ammonium carboxylate salt. Heating the salt to above 100 °C will drive off water and lead to the formation of the amide.
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Conjugate addition is the vinylogous counterpart of direct nucleophilic addition. A nucleophile reacts with a α,β-unsaturated carbonyl compound in the β position. The negative charge carried by the nucleophile is now delocalized in the alkoxide anion and the α carbon carbanion by resonance.