AROMATIC COMPOUNDS DPP-1

S.No. Compound Rate of Electrophilic

Aromatic Substitution

Cl CH3

1.
(I) (II) (III)

Cl OCH3

2.
(I) (II) (III)

CH3 NO2

3.
(I) (II) (III)

OH CH3

4.
(I) (II) (III)


O OH

5.
(I) (II)

6.
(I) (II) (III) (IV) (V)

1
S.No. Compound Rate of Electrophilic
Aromatic Substitution

NH2 NO2

7.
(I) (II) (III)

NHCOCH3 NH2

8.
(I) (II)

OH Cl NH2 NO2 CH3

9.
(I) (II) (III) (IV) (V) (VI)

CH3 Cl

10.
(I) (II)

Cl CHO

11.
(I) (II) (III)

Cl CH3 OH

12.
(I) (II) (III)

CH3 CH3 CH3

13.
(I) (III)
OH CH3
(II) (IV)

COOH OH

14.
(I) (II) (III) (IV)

2
S.No. Compound Rate of Electrophilic
Aromatic Substitution

NO2 NO2 CH3 NO2

15.
Cl NO2
CH3 CH3 Cl CH3
(I) (II) (III) (IV)

OCH3 NO2 Cl

16.
(I) (II) (III) (IV) (V)

NO2 NO2 NO2

17.
NO2 NO2 NO2
Cl OH CH3
(I) (II) (III)

18. acetanilide (C6H5NHCOCH3), acetophenone (C6H5COCH3), aniline, benzene

(I) (II) (III) (IV)

19. chlorobenzene, p-chloronitrobenzene, 2,4-dinitrochlorobenzene

(I) (II) (III)

20. 2,4-dinitrochlorobenzene, 2,4-dinitrophenol

(I) (II)

21. m-dinitrobenzene, 2,4-dinitrotoluene

(I) (II)

"Success comes through

Dedication,
Determination, and
Discipline & Desire."
3
AROMATIC COMPOUNDS DPP-2
S.No. Compound Ortho para Meta director Activating Deactivating
directing directing

NH2

1.

CH3

2.

3.

CF3

4.

NHCH3

5.

NHCOCH3

6.

OCH3

7.

Cl

8.

Br

9.

SO3H

10.

4
S.No. Compound Ortho para Meta director Activating Deactivating
directing directing
CN

11.

COOH

12.

CHO

13.

COOCH3

14.

NO2

15.

COCH3

16.


NH3

17.

"Patience and Silence are the two

powerful energies. Patience makes
you mentally strong and Silence
makes you emotionally strong."
5
AROMATIC COMPOUNDS DPP-3

Identify the product formed during the reaction.

Reactent
Cl
AlCl3 AlCl3
1. + Cl 2. +

O
AlCl3 AlCl3
3. + CH3 – Cl 4. + CH3 – CH2 – C – Cl

O O
5. + Ph – C – Cl AlCl3 6. + C – Cl AlCl3

AlCl3 AlCl3
7. O 8.
Cl Cl–C
||
O

Cl AlCl3
9. + 10. + 3Cl2
h

AlCl3 AlCl3
11. + Cl2 12. + Br – Cl

H2SO4 + AlCl3
13. + HNO3 14.
Cl

15. + Cl AlCl3

Compare rate for electrophilic aromatic substitution

CH3 OH NO2

16. (A) 17. (B)

6
 Cl OH NO2 NO2

18. (C) 19. (D)

NO2

O
||
OCH3 Cl NO2 NO2 NH2 NH–C–CH3

20. (E) 21. (F)

Match the column :

22. Column-I Column-II

R

(A) AlCl3
+ R–Cl  (P) Friedel craft alkylation


O
O
(B) AlCl3 R (Q) Friedel craft acylation
+R – C – Cl

NO2

(C) H2SO4 (R) Nitration

+HNO3

Cl

(D)
AlCl3 (S) Halogenation
+ Cl2

(T) Substitution reaction

‘‘Be motivated, be creative, be passionate’’

7
AROMATIC COMPOUNDS DPP-4

Cl2 / AlCl3
A+B
Cl / AlCl3
C+D
O
1.
Cl / AlCl3
E+F
HNO3,H2SO4
G+H
Conc.H2SO4
I+J

Cl2 / AlCl3
A+B
Cl Cl / AlCl3
C+D
O
2.
Cl / AlCl3
E+F
HNO3,H2SO4
G+H
Conc.H2SO4
I+J

Cl / AlCl3
A+B
Cl / AlCl3
O C+D
O
3. C O
Cl / AlCl3
E+F
HNO3,H2SO4
G+H
Conc.H2SO4
I+J

Cl2 / AlCl3
A+B
Cl / AlCl3
C+D
O
O
4. NH C
Cl / AlCl3
E+F
HNO3,H2SO4
G+H
Conc.H2SO4
I+J

8
 Cl2 / AlCl3
A+B
NO2 Cl / AlCl3
C+D
O
5.
Cl / AlCl3
E+F
HNO3,H2SO4
G+H
Conc.H2SO4
I+J

Cl2 / AlCl3
O A+B
O – C – CH3 Cl / AlCl3
C+D
O
6.
Cl / AlCl3
E+F
NH–C–CH3 HNO3,H2SO4
G+H
O
Conc.H2SO4
I+J

Cl2 / AlCl3
A+B
CH3 Cl / AlCl3
C+D
O
7. Cl / AlCl3
E+F
NH–C–CH3 HNO3,H2SO4
G+H
O Conc.H2SO4
I+J

Cl2 / AlCl3
A+B
Cl / AlCl3
C+D
O
8.
Cl / AlCl3
E+F
CH3 HNO3,H2SO4
G+H
Conc.H2SO4
I+J

Cl2 / AlCl3
A+B
O
Cl / AlCl3
O–C–CH3 C+D
CH3 O
9.
O Cl / AlCl3
E+F
O HNO3,H2SO4
G+H
Conc.H2SO4
I+J

9
 ANSWER KEY OF DPP NO. 1 TO 4

Answer Key of DPP No. 1

1. III > I > II 2. III > I > II 3. II > I > III 4. II > III > I
5. I > II 6. II > III > IV > V > I 7. I > III > II 8. II > I
9. IV > II > VI > I > III > V 10. I > II 11. I > II > III 12. III > II > I
13. II > IV > I > III 14. III > IV > I > II 15. III > I > II > IV
16. III > II > I > V > IV 17. II > III > I 18. III > I > IV > II 19. I > II > III
20. II > I 21. II > I

Answer Key of DPP No. 2

S.No. Ortho para directing Meta directing Activating Deactivating
1.  
2.  
3.  
4.  
5.  
6.  
7.  
8.  
9.  
10 .  
11 .  
12 .  
13 .  
14 .  
15 .  
16 .  
17 .  

10
 Answer of DPP No- 3
O
CH3
1. 2. 3. 4.

Ph
5. 6. O 7. 8.
O
O
H Cl Cl
Cl H H
+ AlCl3 Cl
9. 10. Cl 11.
H H
Cl Cl
H Cl

Br NO2

12. 13. 14. 15.

16. (A) I > II > III 17. (B) I > II > III 18. (C) III > I > II 19. (D) I > II > III
20. (E) I > II > III 21. (F) II > III > I 22. A  P,T; B  Q,T; C  R,T; D S,T;

Answers of DPP No- 4

1. Single product
Cl O

A&B= C&D= E&F=

NO2 SO3H

G&H= I&J=

Cl Cl Cl Cl
Cl
2. A= B= C= D=

Cl
(major) (major)

Cl Cl Cl Cl
O
NO2
E= F= G= H=

NO2
O
(major) (major)

11
 Cl
Cl
SO3H
I= J=

SO3H
(major)

O
O
3. A= C–O B= C–O
(major)

O O
C= C–O D= C–O
(major)
O
O O O
E= C–O F=
C–O
(major)

NO2
O O
G= C–O NO2 H= C–O
(major)
SO3H
O O
I= C–O SO3H J= C–O
(major)
Cl
O O
4. A = Cl NH – C B= NH – C
(major)

O
O
C= NH – C D= NH – C
(major)

O
O
O
E= NH – C F= NH – C
O (major)

NO2
O O
G = NO2 NH – C H= NH – C
(major)
SO3H
O O
I = HO3S NH – C J= NH – C
(major)

12
5. Single product
NO2

A&B= C & D = No reaction E & F = No reaction

Cl
NO2 NO2

G&H= I&J=
NO2 SO3H

O O O
O – C – CH3 O – C – CH3 O – C – CH3
Cl
6. A= B= C=
Cl
NH – C – CH3 NH – C – CH3 NH – C – CH3
(major) O O (major) O

O O O
O – C – CH3 O – C – CH3 O – C – CH3

D= E= F= O
O
NH – C – CH3 NH – C – CH3 NH – C – CH3
O (major) O O

O O O
O – C – CH3 O – C – CH3 O – C – CH3
NO2

G= H= I=
NO2 SO3H
NH – C – CH3 NH – C – CH3 NH – C – CH3
(major) O O (major) O

O
O – C – CH3
SO3H
J=

NH – C – CH3
O

13
 CH3 CH3 CH3
Cl
7. A= B= C=
Cl
NH – C – CH3 NH – C – CH3 NH – C – CH3
(major) O O (major) O

CH3 CH3 CH3

D= E= F= O

NH – C – CH3 O NH – C – CH3
NH – C – CH3
O (major) O O

CH3 CH3 CH3

NO2
G= H= I=
NO2 SO3H
NH – C – CH3 NH – C – CH3 NH – C – CH3
(major) O O (major) O

CH3
SO3H
J=

NH – C – CH3
O

Cl
8. A= B= C= D=
Cl
CH3 CH3 CH3 CH3
(major) (major)

O
NO2
E= F= G= H=
NO2
CH3 O CH3 CH3 CH3
(major) (major)

SO3H

I= J=
SO3H
CH3 CH3
(major)

14
 O O O
O – C – CH3 O – C – CH3 O – C – CH3
Cl
9. A&B= C&D= E&F=
O

C – O – CH3 C – O – CH3 C – O – CH3

O O O

O O
O – C – CH3 O – C – CH3
NO2 SO3H
G&H= I&J=

C – O – CH3 C – O – CH3
O O

15