CHEM 202

Electrophilic Aromatic Substitution worksheet

Give the major product of the following reactions:

NO2 Br NO2
Br2, FeBr3
a)

CH(CH3)CH2CH3
CH3CH2CH2CH2Br, AlCl3
b)

CH2CH2CH3
O
1) ClCCH2CH3, AlCl3
c)
2) H2, Pd on C

OCH3 OCH3

d) CH2=CHCH3
NHCOCH3 (CH3)2CH NHCOCH3
HF
OC(CH3)3 OC(CH3)3
1) SO3, H2SO4
e)
2) Cl2, FeCl3
+
3) Dil. H3O Cl
Br Br
f) KMnO4
H2O
CO2H

g) 1) NaOH , 350oC OH
SO3H
+
2) H3O workup
Cl Cl
h) HO Cl2, FeCl3
NO2 HO NO2

Cl
Give a mechanism for the following reaction:
H
CH3
CH2 Cl-AlCl3

CH2Cl
CH3
AlCl3
+ HCl

CH3
H
Cl-AlCl3