EAS - Some Lewis acid SO 3 H H 2 SO 4 N O O HNO 3 X Strong...

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E E H Note: one carbon becomes a C+, but in the same step another C becomes sp3, (it was carrying an H from the start, and it now has the E attached). This H on the sp3 carbon is ideal for deprotonation - returning the ring to a super stable aromatic system! E General Reaction scheme for EAS - always the same steps, the only thing that changes is the exact nature of the Electrophile and the curved arrow(s) that may be needed at that point. E Reagents B: X X 2 / FeCl 3 X 2 / AlCl 3 First step of reaction X X Fe Cl Cl Cl Once X is attached, the mechanism continues as above. A halide (that detaches from the Lewis complex) can serve as the base for final deprotonation diatomic halogen
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Unformatted text preview: Some Lewis acid SO 3 H H 2 SO 4 N O O HNO 3 X Strong acids and EAS sulfonium ion nitronium ion SO 3 H N O O Final product Final product A Lewis complex forms between X 2 and the Lewis acid, this leads to a very strong electrophilic center Final product Friedel-Crafts C R O Cl FeCl 3 acylium ion C R O acid chloride Some Lewis acid C O R Final product Halogens and EAS C+ sources C R R Cl R FeCl 3 Some Lewis acid H 2 SO 4 Stable carbocations (like secondary, tertiary, resonance-stabilized) can be formed from alkyl halides or in strong acid additions C R R R C R R Final product R Final product Nolta, 2008...
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