Explain Vinylic substitution.
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Answer:
Vinylic halides are unreactive towards nucleophilic substitution reaction. In practice, halogen atoms of vinyl halides are found to be inert. The vinyl halide is the resonance hybrid of the following two structures. CH2=CH−X⟷−CH2−CH=X
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Explanation:
the replacement of substituents in the vinylic position by anionic or neutral nucleophiles. Its division according to mechanistic routes suffers from the fact that for many systems there is a strong connection and mutual intercalation between several routes, and similarities in the behavior of different systems. The chapter also discusses various criteria used for differentiation between the mechanistic pathways. Nucleophilic vinylic substitutions, owing to the inertness of simple vinyl halides, have the reputation of being difficult to conduct. The relative inertness of the unsubstituted vinyl halides compared to their saturated analogues is ascribed to the operation of the +M effect of the halogens. The partial double-bond character of the carbon-halogen bond makes the bond cleavage more difficult. The transmission of electronic effects of electron-attracting substituents that are bonded to the second vinylic carbon via the same rr-system helps the nucleophilic attack. Nucleophilic vinylic substitutions are closely related to nucleophilic aromatic substitutions, as in both the leaving group leaves from an unsaturated carbon atom. Stereochemical study of the reaction can give information on the lifetime of the intermediate and about the structure of the transition state, which is not available in aromatic systems. The stereochemistry of the substitution depends on the configuration of the substrates and on the specific route involved.