Search results
Results from the WOW.Com Content Network
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 ...
Alkali metal phenolates, such as sodium phenolate hydrolyze in aqueous solution to form basic solutions. [2] At pH = 10, phenol and phenolate are in approximately 1:1 proportions. The phenoxide anion (aka phenolate) is a strong nucleophile with a comparable to the one of carbanions or tertiary amines. [3]
The nucleophile may be electrically neutral or negatively charged, whereas the substrate is typically neutral or positively charged. An example of nucleophilic substitution is the hydrolysis of an alkyl bromide, R-Br under basic conditions, where the attacking nucleophile is hydroxyl (OH −) and the leaving group is bromide (Br −).
For example, OH − is a better nucleophile than water, and I − is a better nucleophile than Br − (in polar protic solvents). In a polar aprotic solvent, nucleophilicity increases up a column of the periodic table as there is no hydrogen bonding between the solvent and nucleophile; in this case nucleophilicity mirrors basicity.
The rate equation for S N 2 reactions are bimolecular being first order in Nucleophile and first order in Reagent. The determining factor when both S N 2 and S N 1 reaction mechanisms are viable is the strength of the Nucleophile. Nuclephilicity and basicity are linked and the more nucleophilic a molecule becomes the greater said nucleophile's ...
As nucleophiles, organolithium reagents undergo carbolithiation reactions, whereby the carbon-lithium bond adds across a carbon–carbon double or triple bond, forming new organolithium species. [32] This reaction is the most widely employed reaction of organolithium compounds.
The following is the reaction mechanism of a nucleophilic aromatic substitution of 2,4-dinitrochlorobenzene (1) in a basic solution in water. Nucleophilic aromatic substitution Since the nitro group is an activator toward nucleophilic substitution, and a meta director, it is able to stabilize the additional electron density (via resonance) when ...
Ammonolysis refers to solvolysis by ammonia, but can also describe nucleophilic attack by ammonia more generally. Ammonia boils at −33 °C, and, as such, is rarely used as a solvent in its pure form. It is, however, readily miscible with water, and is commonly used in the form of a saturated aqueous solution. For this reason, ammonolysis may ...