BAKLIWAL TUTORIALS

ORGANIC CHEMISTRY CLASS TEST TOPIC: AROMATIC HYDROCARBON

SECTION-I
Each question has 4 choices (A), (B), (C) and (D) for its answer, out which ONLY ONE is correct.
(+3, - 1)

1. Which one of the following intermediates will have the lowest energy in the energy profile diagram?
H H H H
E E E E
   
NO2
(a) (b) (c) (d)
NO2
NO2
2. The following three isomeric tribromobenzenes are subjected to mononitration.
Br Br Br
Br Br

Br Br Br
Br
(I) (II) (III)
Which of these would produce three possible mononitrotribromobenzenes ?
(a) (II) and (III) (b) (I) and (II)
(c) (II) (d) (III)
3. What is the correct order of reactivity of the following alkylhalide towards Friedal-Craft’s alkylation
with benzene in the presence of AlCl3?
(a) CH3–F > CH3–Cl> CH3–Br > CH3–I (b) CH3F < CH3–Cl< CH3–Br < CH3–I
(c) CH3–F > CH3–Br > CH3–Cl> CH3–I (d) CH3F < CH3–Br < CH3–Cl< CH3–I

4. Benzene reacts with sulphuric acid to form benzenesulphonic acid, only when the sulphuric acid is
(a) cold and dilute (b) hot and dilute
(c) hot and concentrated (d) mixed with HNO3
CH3O O
AlCl3 CH3–C–Cl
5. + CH3 – C– C – Cl  A AlCl3/ B
CH3
What is the major product ‘B’?
O O
C–C(CH3)3 C–C(CH3)3 C(CH3)3 C(CH3)3
C–CH3
(a) (b) (c) (d)
C–CH3 O
O C–CH3 C–CH3
O O
NR2
HONO
6. P. P is
NR2 NO OH

(a) (b) (c) (d)

NO
7. The major product formed on monobromination of phenylbenzoate is
Br
(a) O (b) O
Br
O O
Br
(c) O (d) O
O O
Br

HO O
C
Ph Ph
H+
8. (P) (Major)

Ph
The compound (P) will be
Ph O Ph
Ph O Ph
(a) Ph C Ph (b) Ph C Ph
Ph Ph Ph
O
Ph C
Ph Ph
(c) (d)
Ph
Ph
9. The major product formed in the reaction
OMe
AlCl3
+ (CH3)2CHCH2Br
OMe
OMe
(a) (b)
CH2CH(CH3)2 (CH3)2CHCH2
OMe OMe
(c) (d)
C(CH3)3 (CH3)3C

10. Arrange the following compounds in order of decreasing reactivity for aromatic electrophilic
substitution reactions :
CH3 CH3 CH3
CH3

H3C CH3
1 2
CH3
3
Select the correct answer from the codes given below :
(a) 1 > 2 > 3 (b) 3 > 2 > 1 (c) 1 > 3 > 2 (d) 2 > 1 > 3
 SECTION-II
Each question has 4 choices (A), (B), (C) and (D) for its answer, out which ONE OR MORE is/are
correct. (+3, -2)

11. Which of the following group are o–p director but ring deactivator towards Electrophillic Aromatic
substitution?
(a) –NO2 (b) –OCH3 (c) –CH=CH–COOH (d) –NO
12. A Friedel-Crafts reaction of benzene with chloroform produces
Cl C6H5
(a) C6H5CHCl2 (b) C6H5–C–C6H5 (c) C6H5–C–C6H5 (d) C6H5CCl3
H H
13. In which case, SE will not be at meta position?
O
+
CF3 N(CH3)3 SOOH NH–C–CH3

(a) (b) (c) (d)

14. Consider the following statements for electrophilic aromatic substitution and select the correct
statements.
(a) C6H5–OH is more reactive than C6H5–S–H
(b) C6H5–S–H is more reactive than C6H5–O–H
(c) C6H5–NHCH3 is more reactive than C6H5OCH3
(d) C6H5–OCH3 is more reactive than C6H5–NHCH3

15. Which of the following statement(s) are correct?

(a) An activating groups is an electronreleasing group.
(b) An activating group activates all positions of the benzene ring.
(c) An activating group activates only the ortho and parapositions in the benzene ring.
(d) The effect of any groupwhether activating or deactivating is the strongest at the ortho and para
positions in the benzene ring.

16. Which among the following is correctly matched?

(a) C6H5CH3 ; o, p-directing group

(b) C6H5 N H 3 ; m-directing group
(c) C6H5CH = CH2 ; o, p-directing group
O

(d) CH3 O P O ; m-directing group

O — CH3
17. How many isomers can be formed on mono-bromination of the following compound?

(a) 3 (b) 5 (c) 7 (d) none of these

18. How many isomers can be formed on mono-nitration of the following compound?
 (a) 5 (b) 3 (c) 8 (d) 1

SECTION-III (Paragraph Type)

Each question has 4 choices (A), (B), (C) and (D) for its answer, out of which ONLY ONE is correct.
(+3, -1)

Benzene and other aromatic rings have tendency to undergo electrophilic aromatic substitution reactions and
do not undergo electrophilic addition reactions like alkenes and alkynes.
Monosubstituted benzenes undergo substitution reactions either faster or slower than benzene
depending on the fact that whether the group is electron donating or electron withdrawing, respectively. The
directive influence of a group is determined by the fact that the arenium formed by the attack of electrophile
on a particular position is more stable than the arenium ion formed by attacking other positions.
Side chain oxidation of benzene gives benzoic acid irrespective of the length or nature of the side
chain.

19. Rank the following compounds in the decreasing order of their reactivity towards electrophilic
substitution.

NHCOCH3 ONa NH3 CHCl2

(1) (2) (3) (4)

(a) (1) > (2) > (4) > (3) (b) (2) > (1) > (4) > (3)
(c) (2) > (1) > (3) > (4) (d) (4) > (1) > (2) > (3)

20. In the given compound,

5 4
6 3

7 2
8
N1
H
the electrophile (E) would mainly attack on
(a) position 4 (b) position 5
(c) position 6 (d) position 8