Electrophile vs. Nucleophile (an overview)

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  •  Electrophile: (literally electron lovers), Electron deficient, affinity towards electron, Lewis acid
  •  -Most of them are positively charged, have an atom that carries a partial positive charged or an atom with an incomplete octet.-participates in a chemical reaction by accepting an electron pair in order to bond to a nucleophile

  • -They may be:
  • 1.Cations like H+, NO+
  • 2.Polarized neutral molecules like HCl, alkyl halides, acyl halides and carbonyl compounds
  • 3.Polarizable neutral molecules like Cl2, Br2
  • 4.Oxidizing agents like organic per acids
  • 5.Chemical species that do not satisfy the octet rule like carbenes and radicals
  • Some Lewis acids like BH3

  • Nucleophile: (literally nucleus lovers), Electron rich, affinity towards nuclei, Lewis bases
  • -donates an electron pair to an electrophile to form a chemical bond in a reaction.
  • -All molecules or ions with a free pair of electrons or at least one pi bond can act as a nucleophile
  • -They may be:
  • 1. ions such as Cl- or molecule like NH3
  • 2. Carbon nucleophiles: alkyl metal halides (as in Grignard reaction and anion of a terminal alkyne) and Enols (as in condensation reactions like in aldol condensation).
  • 3. Oxygen nucleophiles: water (H2O), hydroxide anion, alcohols, alkoxide anions, hydrogen peroxide, and carboxylate anions.
  • 4. Sulphur nucleophiles: Hydrogen sulphide and its salts like thiols.
  • 5. Nitrogen nucleophiles: ammonia, amines and nitrites.

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