Q.What are electrophiles and nucleophiles? Give suitable examples for each.
Step 1. Nucleophiles. A nucleophile is a reagent with a high affinity for electro-positive centres -- it possesses an atom bearing an unshared (lone) pair of electrons, which it seeks to share with an electron-poor centre to form a new covalent bond, becoming stabilised in the process. Nucleophiles are usually negatively-charged ions or electron-rich neutral molecules, and every Lewis base is a nucleophile. Examples: neutral lone-pair donors such as ammonia (), water (), alcohols (ROH) and thiols (RSH); and negatively-charged nucleophiles such as the halide ions (), hydroxide (), alkoxide () and cyanide ().
Step 2. Electrophiles. An electrophile is the electronic opposite -- a reagent attracted toward negative charge or an electron-rich centre. Electrophiles are either positively-charged ions or electron-deficient neutral molecules (including species like with vacant d-orbitals able to accept electrons), and every Lewis acid is an electrophile. Examples: neutral electrophiles such as , dichlorocarbene (), , and ; and positively-charged electrophiles such as carbocations (), the proton (), oxonium (), nitrosonium () and nitronium ().
Step 3. The relationship. In virtually every organic reaction covered in this unit, a nucleophile and an electrophile react with each other -- the nucleophile's lone pair forms a new bond at the electrophile's electron-deficient centre, which is exactly the electron movement captured by curved-arrow notation.
Nucleophiles ('nucleus-loving') are Lewis bases -- negatively-charged or lone-pair-bearing neutral species (e.g. OH⁻, CN⁻, NH₃, H₂O) that donate an electron pair to an electropositive centre. Electrophiles ('electron-loving') are Lewis acids -- positively-charged or electron-deficient neutral species (e.g. H⁺, ⁺NO₂, BF₃, AlCl₃) that accept an electron pair from an electron-rich centre.
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