Electrophilic Aromatic Substitution

Electrophilic Aromatic Substitution - Aromatic compounds...

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Aromatic compounds such as benzene undergo electrophilic aromatic substitution reactions I thought benzene was stable and unreactive…how is it behaving as a Nu:?
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Recall …
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5/1/2010 3 Although benzene behaves similarly in step 1 (generation of carbocation intermediate), step 2 is not the same as for alkenes…. Why?
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Benzene is a nucleophile that reacts with an electrophile, Although benzene’s pi electrons are in a stable aromatic system, they are available to attack a strong electrophile to give a carbocation. An electrophilic substitution yields an aromatic product which is significantly more stable than the addition reaction Aromaticity is regained by loss of a proton.
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Reaction Coordinate Diagrams for the Two Benzene Reactions RULE - most reactions proceed to yield the most stable product because this yields the most favorable G Why would the generation of an aromatic product be favored?
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General Mechanism for Electrophilic Aromatic Substitution of Benzene Resonance-stabilized carbocation is called a sigma complex because the electrophile is joined to the benzene ring by a new sigma bond
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This note was uploaded on 12/10/2010 for the course CHE 179582 taught by Professor Rzayev during the Spring '09 term at SUNY Buffalo.

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Electrophilic Aromatic Substitution - Aromatic compounds...

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