Chemistry

Substitution and elimination

Substitution and elimination



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Nucleophiles at S.N2Reactions

There are a large number of SNReactions, they always involve competition between the attacking nucleophile and the leaving group. The nucleophiles are often anions, which are usually used as lithium, sodium or potassium salts. Some representative examples of such nucleophiles are:

  • Metal alkoxides, with the alcoholate as the reacting nucleophile
  • Metal carboxylates, with the carboxylate anion as the nucleophile
  • Metal thioloates with the sulfide as an anionic group
  • Metal cyanides, with the cyanide anion as the nucleophilic center

Neutral molecules with a lone pair of electrons can also react as nucleophiles, such as amines or water. Nucleophiles always have a lone pair of electrons and are therefore also bases and can thus also result in elimination reactions. However, the chemical terms basicity and nucleophilicity are not to be equated! The competition between the basicity and nucleophilicity of the nucleophile is critical to the product ratio.

definition
Nucleophilicity is a kinetic quantity that indicates how quickly a molecule or ion reacts. In the case of basicity, on the other hand, only the position of the reaction equilibrium is described.


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