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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.
An example of a reaction proceeding in a S N 1 fashion is the synthesis of 2,5-dichloro-2,5-dimethylhexane from the corresponding diol with concentrated hydrochloric acid: [8] As the alpha and beta substitutions increase with respect to leaving groups, the reaction is diverted from S N 2 to S N 1.
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).
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] S N i reaction mechanism Sn1 occurs in tertiary carbon while Sn2 occurs in primary carbon
Substitution reactions in organic chemistry are classified either as electrophilic or nucleophilic depending upon the reagent involved, whether a reactive intermediate involved in the reaction is a carbocation, a carbanion or a free radical, and whether the substrate is aliphatic or aromatic. Detailed understanding of a reaction type helps to ...
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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]
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