ANDHERI / BORIVALI / DADAR / CHEMBUR / THANE / MULUND/ NERUL / POWAI

IIT JEE - 2014

TIME: 1 HR

TW TEST
TOPICS: AROMATIC HYDROCARBON

MARKS: 65
DATE:

SECTION-I
This section contains 10multiple choice questions. 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)
(III)
(II)
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-Crafts alkylation
with benzene in the presence of AlCl3 ?
(a) CH3F > CH3Cl> CH3Br > CH3I
(b) CH3F < CH3Cl< CH3Br < CH3I
(c) CH3F > CH3Br > CH3Cl> CH3I
(d) CH3F < CH3Br < CH3Cl< CH3I

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
O

CH3 O

+ CH3 C C Cl

5.

AlCl3

CH3CCl
AlCl3/

CH3

What is the major product B?

O
CC(CH3)3

O
CC(CH3)3

(a)

(b)
CCH3
O

(c)
CCH3
O

Head Office: Andheri: 26245223

C(CH3)3

C(CH3)3

(d)

CCH3
O

CCH3
O

MUMBAI / DELHI/ AKOLA / KOLKATA / LUCKNOW

NR2
HONO

6.

P.

P is
OH

NO

NR2

(a)

(b)

(c)

(d)

NO

7.

The major product formed on monobromination of phenylbenzoate is

Br
(a)
(b)
O
O
Br
O
O
Br
(c)
(d)
O
O

O
HO

Ph

Br

O
Ph

8.

H+

(P) (Major)

Ph
The compound (P) will be
Ph O Ph

(a) Ph

C
Ph

Ph

O Ph
C

(b) Ph

Ph
Ph

Ph
Ph

O
Ph

Ph

(c)
Ph

9.

Ph

(d)
Ph

The major product formed in the reaction

OMe
AlCl3
+ (CH3)2CHCH2Br
(a)

OMe

OMe

(b)
(CH3)2CHCH2

CH2CH(CH3)2
OMe

(c)

OMe
(d)

C(CH3)3

Head Office: Andheri: 26245223

(CH3)3C

MUMBAI / DELHI/ AKOLA / KOLKATA / LUCKNOW

10.

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

H3 C

CH3

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
This section contains 7 multiple choice questions. Each question has 4 choices (A), (B), (C)
and (D) for its answer, out which ONE OR MORE is/are correct.
(+3, 0)
11.

Which of the following group are op director but ring deactivator towards Electrophillic Aromatic
substitution?
(a) NO2
(b) OCH3
(c) CH=CHCOOH
(d) NO

12.

A Friedel-Crafts reaction of benzene with chloroform produces

Cl
C6H5
(b) C6H5CC6H5

(a) C6H5CHCl2

(c) C6H5CC6H5

13.

(d) C6H5CCl3

In which case, SE will not be at meta position?

O
+

CF3
(a)
14.

(b)

NHCCH3

SOOH

N(CH3)3

(c)

(d)

Consider the following statements for electrophilic aromatic substitution and select the correct
statements.
(a) C6H5OH is more reactive than C6 H5SH
(b) C6H5SH is more reactive than C6 H5OH
(c) C6H5NHCH3 is more reactive than C6 H5OCH3
(d) C6H5OCH3 is more reactive than C6H5NHCH3
R
NNO2

15.

Conc. H2SO4

NHR
(a)
16.

NO2

Products can be

NHR

(b)

NO2

NHNO2
(c)

(d) No reaction

Which of the following statement(s) are correct?

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

17.

Which among the following is correctly matched?

(a) C6H5CH3 ; o, p-directing group

(b) C6H5 N H 3 ; m-directing group

(c) C6H5CH = CH2 ; o, p-directing group
O

(d) CH3

; m-directing group

O CH3

SECTION-III

(Paragraph Type)

This section contains 2 groups of questions. 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.
18.

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)

(c) (2) > (1) > (3) > (4)

19.

(b) (2) > (1) > (4) > (3)

(d) (4) > (1) > (2) > (3)

In the given compound,

5

7
8

N1

the electrophile (E) would mainly attack on

(a) position 4
(b) position 5
(c) position 6
(d) position 8

Head Office: Andheri: 26245223

MUMBAI / DELHI/ AKOLA / KOLKATA / LUCKNOW

SECTION-IV

(Integer Answer Type)

This section contains 2 questions. The answer to each of the questions is a single digit integer,
ranging from 0 to 9. The correct digit below the question number in the ORS is be bubbled.
(+4, 0)

20.

How many isomers can be formed on mono-bromination of the following compound?

21.

How many isomers can be formed on mono-nitration of the following compound?

Head Office: Andheri: 26245223

MUMBAI / DELHI/ AKOLA / KOLKATA / LUCKNOW

ANDHERI / BORIVALI / DADAR / CHEMBUR / THANE / MULUND/ NERUL / POWAI

TOPICS: AROMATIC HYDROCARBON(ANSWER KEY)

1.d

2.c

3.b

4.c

5.c

6.a

7.d

8.c

9.d

10.c

11.c, d

12.a, b, c

13.b, d

14.a, c

15.a, b, c

16.a, b, d

17.a, b, c

18.b

19.c

20.7

21. 3

Head Office: Andheri: 26245223

MUMBAI / DELHI/ AKOLA / KOLKATA / LUCKNOW

AROMATIC HYDROABON SOLUTION

1.

(d)
Presence of electron withdrawing group will decrease the stability and increase the energy of the
arenium ion. Therefore, arenium ion without NO2 group will be most stable.

2.

(c)
Remaining three position in (II) are different.

3.(b)

4.(c)

8.(c)

5.(c)

9.(d)

13.(a), (b)
18.

6.(a)

10.(c)
14.(a), (c)

7.(d)

11.(c), (d)

12.(a), (b), (c)

15.(a), (b), (c) 16.(a, b, d)

17.(a, b, c)

(b)
C6H5ONa is most reactive towards electrophilic substitution as O strongly activates the benzene
ring. C6H5NHCOCH3 is less reactive as the lone pair of electrons of Natom is partially available
and hence moderately activates the benzene ring. The CHCl2 group of C6H5CHCl2 weakly

deactivates the benzene ring whereas _ N H 3 group of C 6 H 5 NH 3 strongly deactivates the benzene

ring.
19.

(c)
In the given compound, the electrophile (E+) would mainly attack at position 6 because the
intermediate arenium ion is relatively more stable.
E
H

..
N
H

E
H
+

..
N

E
H

(more stable)

Arenium ion

20.

21.

E
H
+

N
H