Aromatic Synthesis : Answer Key

A.
meta director
SO3H Cl SO3H
SO3, H2SO 4 Cl2, Fe

B.
o,p director

(CH3)2CHBr Br2, Fe
AlCl3
Br

C.
meta director
O2 N O2 N Br H 2N Br
HNO3, H2SO 4 Br 2, Fe H2, Pd/C

D.
meta director
O2 N O2 N Br H 2N Br
HNO3, H2SO 4 Br 2, Fe H2, Pd/C

NaNO2, HCl
H2O, 0ºC

F Br N2 Br
HBF 4
heat

E.
meta director
O2 N O2 N SO3H O2 N OH
HNO3, H2SO 4 SO3 NaOH
H2SO 4 H 2O
F.
meta director both m directors Cl

HNO3 SO3 Cl2

H2, Pd/C
Cl

HO3S NH2

G.
meta director

SO3 Br 2 NaOH
H2SO 4 SO3H Fe Br SO3H H 2O Br OH

(CH3)2CuLi

CH3 OH

H.
O O,P director
SO3H OH O
SO3 NaOH Cl
H2SO 4 H 2O pyridine O

CH3Cl
AlCl3
O
OH
NaOH
O
H 2O H 3C
H 3C
I.
O o,p director
SO3H OH O
SO3 NaOH Cl
H2SO 4 H 2O pyridine O

HNO3
H2SO 4
OH O
NaOH H2 O
H 2O O Pd/C
H 2N H 2N O
O2 N

J.
meta director
SO3H Br SO3H Br OH
SO3 Br 2 NaOH
H2SO 4 Fe H 2O

K.
o,p director
O
H
NO2 NH2 N
HNO3 H2 Cl
H2SO 4 Pd/C pyridine O

CH3Cl Br 2, Fe
AlCl3
NaNO2 H H
N2 NH2 N N
(CH3)2CuLi
HCl, H2O NaOH
0ºC H 2O O O
H 3C H 3C H 3C Br

CuCN

CN CO2H
H 3O +

H 3C H 3C
L.
meta director
O2 N O2 N Br O2 N CH3
HNO3 Br 2 (CH3)2CuLi
H2SO 4 Fe

H2, Pd/C

NaNO2
HO2C CH3 Br CH3 N2 CH3 HCl, H O H2N CH3
1. Mg CuBr
2
2. CO2 0ºC

M.
o,p director
O
H
NO2 NH2 N
HNO3 H2 Cl
H2SO 4 Pd/C pyridine O

SO3
H2SO 4
CH3 CH3 CH3 o,p director
H H H
NH2 N N
NaOH H 3O + CH3Cl N

H 2O heat O AlCl3
O O
HO3S HO3S
H2SO 4 meta
HNO2 CH3 director
CH3 CH3
H2O, 0ºC N2 CN CO2H
CuCN H 3O +