Wednesday 18 December 2013

carbocation and Electrophilic Aromatic Substitution 

Overall an electrophilic aromatic susbtitution (EArS) can be represented as follows:
Electrophilic aromatic substitution
There are three fundamental components to an electrophilic aromatic substitution mechanism:
  1. formation of the new σ bond from a C=C in the arene nucleophile
  2. removal of the proton by breaking the C-H σ bond
  3. reforming the C=C to restore the aromaticity
curly arrows for electrophilic aromatic substitution
The mechanism is represented by the following series of events:
  • Formation of the reactive electrophile, E(not shown here) from the reagents
  • Slow reaction of the arene C=C with the E+ to give a resonance stabilised carbocation (see below)
  • Loss of H+ from the carbocation to restore the C=C and the aromatic system
cyclohexadienyl cation = arenium ion
The reaction of the electrophile E+ with the arene is the slow step since it results in the loss of aromaticity even though the resulting cation is still resonance stablised.
 This carbocation is also described as the cyclohexdienyl cation or arenium ion or as a sigma-complex

When phenol undergoes eas .carbo cation intermediate is formed which is stablized only at ortho and at para position.Not at meta position.

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