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Substrates with adjacent pi C=C systems can favor both S N 1 and S N 2 reactions. In S N 1, allylic and benzylic carbocations are stabilized by delocalizing the positive charge. In S N 2, however, the conjugation between the reaction centre and the adjacent pi system stabilizes the transition state.
In this type of substitution reaction, one group of the substrate participates initially in the reaction and thereby affects the reaction. A classic example of NGP is the reaction of a sulfur or nitrogen mustard with a nucleophile, the rate of reaction is much higher for the sulfur mustard and a nucleophile than it would be for a primary or secondary alkyl chloride without a heteroatom.
The stereoelectronic effect, which is the interaction shown above when the acceptor orbital is the σ*(Si–CH 3), appears to be a more predominant factor in determining the reaction selectivity against the steric hindrance and even wins over the penalty of the disrupted conjugation system of the product due to steric clash. [23]
A stereospecific mechanism specifies the stereochemical outcome of a given reactant, whereas a stereoselective reaction selects products from those made available by the same, non-specific mechanism acting on a given reactant. Given a single, stereoisomerically pure starting material, a stereospecific mechanism will give 100% of a particular ...
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).
This reaction differs from a common S N 2 reaction, because it happens at a trigonal carbon atom (sp 2 hybridization). The mechanism of S N 2 reaction does not occur due to steric hindrance of the benzene ring. In order to attack the C atom, the nucleophile must approach in line with the C-LG (leaving group) bond from the back, where the ...
Where a represents the minimum distance of approach between complex and ligand in solution (in cm), N A is the Avogadro constant, R is the gas constant and T is the reaction temperature. V is the electrostatic potential energy of the ions at that distance: V = z 1 z 2 e 2 /4πaε. Where z is the charge number of each species and ε is the ...
An energy profile of an enantioselective addition reaction. Many of the building blocks of biological systems such as sugars and amino acids are produced exclusively as one enantiomer. As a result, living systems possess a high degree of chemical chirality and will often react differently with the various enantiomers of a given compound ...