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When the solvent is also a nucleophile such as dioxane two successive S N 2 reactions take place and the stereochemistry is again retention. With standard S N 1 reaction conditions the reaction outcome is retention via a competing S N i mechanism and not racemization and with pyridine added the result is again inversion. [5] [3]
An example of a reaction taking place with an S N 1 reaction mechanism is the hydrolysis of tert-butyl bromide forming tert-butanol: This S N 1 reaction takes place in three steps: Formation of a tert-butyl carbocation by separation of a leaving group (a bromide anion) from the carbon atom: this step is slow. [5] Recombination of carbocation ...
A more detailed explanation of this can be found in the main SN1 reaction page. S N 2 reaction mechanism. The S N 2 mechanism has just one step. The attack of the reagent and the expulsion of the leaving group happen simultaneously. This mechanism always results in inversion of configuration.
Sigmatropic rearrangements are concisely described by an order term [i,j], which is defined as the migration of a σ-bond adjacent to one or more π systems to a new position (i−1) and (j−1) atoms removed from the original location of the σ-bond. [3]
An example of a substitution reaction taking place by a so-called borderline mechanism as originally studied by Hughes and Ingold [6] is the reaction of 1-phenylethyl chloride with sodium methoxide in methanol. The reaction rate is found to the sum of S N 1 and S N 2 components with 61% (3,5 M, 70 °C) taking place by the latter.
In the Walden inversion, the backside attack by the nucleophile in an S N 2 reaction gives rise to a product whose configuration is opposite to the reactant. Therefore, during S N 2 reaction, 100% inversion of product takes place. This is known as Walden inversion. It was first observed by chemist Paul Walden in 1896.
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The term "Reverse electron transfer" is used in regard to the reversibility of the reaction performed by complex I of the mitochondrial or bacterial respiratory chain. Complex I is responsible for the oxidation of NADH generated in catabolism when in the forward reaction electrons from the nucleotide (NADH) are transferred to membrane ...