Aromatic

Synthesis : Answer Key

A.
meta director
SO3H

SO3, H2SO 4

Cl

Cl2, Fe

SO3H

B.
o,p director
(CH3)2CHBr

SO3H

Cl2, Fe

AlCl3

Cl

C.
meta director
O2 N

HNO3, H2SO 4

Br 2, Fe

O2 N

Br

H2, Pd/C

H 2N

Br

D.
meta director
HNO3, H2SO 4

O2 N

Br 2, Fe

O2 N

Br

H2, Pd/C

H 2N

Br

NaNO2, HCl
H2O, 0C
F

Br

N2

HBF 4

Br

heat

E.
meta director
HNO3, H2SO 4

O2 N

SO3
H2SO 4

O2 N

SO3H

NaOH
H 2O

O2 N

OH


F.
meta director
HNO3
H2SO 4

SO3
NO2

Cl

both m directors

H2SO 4

Cl2
HO3S

NO2

Fe

HO3S

NO2

H2, Pd/C
Cl

HO3S

NH2

G.

meta director
SO3
H2SO 4

NaOH

Br 2
SO3H

Fe

Br

H 2O

SO3H

Br

OH

(CH3)2CuLi

CH3

OH

H.
O,P director

SO3
H2SO 4

SO3H

OH

NaOH
H 2O

Cl

pyridine
CH3Cl
AlCl3
OH
H 3C

NaOH
H 2O

H 3C

I.
o,p director

O
SO3H

SO3

OH

NaOH

H2SO 4

H 2O

Cl

pyridine

HNO3
OH

NaOH
H 2O

H 2N

H2

Pd/C

H 2N

H2SO 4

O2 N

J.
meta director
SO3H

SO3

Br

Br 2

H2SO 4

SO3H

Br

NaOH

Fe

OH

H 2O

K.
O
NO2

HNO3
H2SO 4

NH2

H2
Pd/C

o,p director
H
N

Cl

pyridine

CH3Cl
N2

NaNO2
HCl, H2O
0C

H 3C

NH2

NaOH
H 2O

H 3C

H 3C

Br 2, Fe

AlCl3

H
N

(CH3)2CuLi
O

Br

H
N
O

CuCN
CN
H 3C

CO2H

H 3O +
H 3C

L.
meta director
HNO3

O2 N

O2 N

Br 2

Br

Fe

H2SO 4

O2 N

(CH3)2CuLi

CH3

H2, Pd/C
HO2C

CH3

1. Mg

Br

CH3

CuBr

NaNO2

CH3 HCl, H O H2N

2

N2

2. CO2

CH3

0C

M.
o,p director

O
NO2

HNO3

NH2

H2
Pd/C

H2SO 4

H
N

Cl

pyridine

SO3
H2SO 4
CH3
NH2

CH3

NaOH

CH3

H
N

H 2O

H 3O +
O

heat

o,p director

H
N
O

HO3S

AlCl3

HO3S

H2O, 0C

CH3
N2

CH3

CuCN

CN

CH3

H 3O +

meta
director

H2SO 4
HNO2

H
N

CH3Cl

CO2H