Reações de Compostos Aromáticos

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Solutions for Reactions of Aromatic Compounds
CH3I
AlCl3
AlCl3
(CH3)3CCl
CH3
C(CH3)3
SO3
H2SO4
HNO3
H2SO4
CH3
SO3H
C(CH3)3
NO2
(Separate from ortho.)
19
(a)
(excess)
(excess)
(b)
(Separate from ortho, although 
steric hindrance would prevent 
much ortho substitution.)
CH3I
AlCl3
CH3
Cl2
AlCl3
Cl
CH3
(Separate from ortho.)
(c)
(excess)
C C(CH3)3
O
Cl
Cl C
O
CH2CH(CH3)2
C C(CH3)3
O
C
O
CH2CH(CH3)2
(b)
+
1) AlCl3
2) H2O
workup
2) H2O
workup
1) AlCl3+
(a)
20 Friedel-Crafts alkylation is typically followed by a water workup to remove AlCl or other catalyst.3
Zn(Hg), HCl
OCH3
Cl C
O
C(CH3)3
Cl C
O
H3CO CHO
C
O
C(CH3)3
C
O
CH2C(CH3)3
AlCl3/CuCl
CO, HCl(d)
2) H2O
workup
1) AlCl3
+
(c)
2) H2O
workup
1) AlCl3
+
(f)
(e)
2) H2O
workup
1) AlCl3
+
Cl
O
O
Zn(Hg), HCl
Making a new bond from benzene to a 1° 
carbon requires Friedel-Crafts acylation 
followed by reduction.
Clemmensen
Clemmensen
The sequence of 
reactions is 
important.
393