Synthesis of benzene derivatives via electrophilic aromatic substitution |
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Date: 15-5-2017
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Date: 12-7-2018
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Date: 21-11-2019
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This section is on the general mechanism of how an electrophilic atom becomes a part of a benzene ring through the substitution of a hydrogen. Common reactions that proceed by electrophilic aromatic substitution include the nitration and sulfonation of benzene, hydration of benzene, Friedel-Crafts acylation and Friedel-Crafts alkylation. The catalysts and co-reagents serve to generate the strong electrophilic species needed to effect the initial step of the substitution. The specific electrophile (E or E+) believed to function in each type of reaction is listed in the right hand column.
Reaction | Reagent | Catalyst | Product | E+ or E |
---|---|---|---|---|
Halogenation |
X2 (X=Cl, Br)
X2 (X = I) |
FeX3
HNO3 |
ArCl, ArBr
ArI |
X+
H2O−I+ |
Nitration | HNO3 | H2SO4 | ArNO2 | +NO2 |
Sulfonation | H2SO4 or H2S2O7 | None | ArSO3H | SO3 |
Friedel-Crafts alkylation | RX, ArCH2X | AlCl3 | Ar-R, Ar-CH2Ar | R+ |
ROH | HF, H2SO4, or BF3 | Ar-R | R+ | |
RCH=CH2 | H3PO4 or HF | Ar-CHRCH3 | R+ | |
Friedel-Crafts acylation | RCOCl | AlCl3 | Ar-COR | RC+=O |
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