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For example, the synthesis of macrocidin A, a fungal metabolite, involves an intramolecular ring closing step via an S N 2 reaction with a phenoxide group as the nucleophile and a halide as the leaving group, forming an ether. [2] Reactions such as this, with an alkoxide as the nucleophile, are known as the Williamson ether synthesis.
The two main mechanisms were the S N 1 reaction and the S N 2 reaction, where S stands for substitution, N stands for nucleophilic, and the number represents the kinetic order of the reaction. [4] In the S N 2 reaction, the addition of the nucleophile and the elimination of leaving group take place simultaneously (i.e. a concerted reaction).
The chemical inverse of a proton sponge would be a hydride sponge. This property is exhibited by C 10 H 6 (BMe 2 ) 2 , which reacts with potassium hydride to afford K[C 10 H 6 (BMe 2 ) 2 H]. [ 9 ]
In organic chemistry, neighbouring group participation (NGP, also known as anchimeric assistance) has been defined by the International Union of Pure and Applied Chemistry (IUPAC) as the interaction of a reaction centre with a lone pair of electrons in an atom or the electrons present in a sigma or pi bond contained within the parent molecule but not conjugated with the reaction centre.
Arrow pushing or electron pushing is a technique used to describe the progression of organic chemistry reaction mechanisms. [1] It was first developed by Sir Robert Robinson.In using arrow pushing, "curved arrows" or "curly arrows" are drawn on the structural formulae of reactants in a chemical equation to show the reaction mechanism.
For example, the substituent may determine the mechanism to be an SN1 type reaction over a SN2 type reaction, in which case the resulting Hammett plot will indicate a rate acceleration due to an EDG, thus elucidating the mechanism of the reaction. Another deviation from the regular Hammett equation is explained by the charge of nucleophile.
The terminology is typically applied to organometallic and coordination complexes, but resembles the Sn2 mechanism in organic chemistry. The opposite pathway is dissociative substitution, being analogous to the Sn1 pathway. Intermediate pathways exist between the pure associative and pure dissociative pathways, these are called interchange ...
An example of a solvolysis reaction is the reaction of a triglyceride with a simple alcohol such as methanol or ethanol to give the methyl or ethyl esters of the fatty acid, as well as glycerol. This reaction is more commonly known as a transesterification reaction due to the exchange of the alcohol fragments. [2]