6 Aromatic Compounds

SECTION-I : STRAIGHT OBJECTIVE TYPE

CH = CH – COOH

6.1 HOCI / H

The major product is :

OH
CH = CH – COOH CH = CH – COOH CH = CH – COOH CH –CH – COOH
CI
(A) (B) (C) (D) CI
CI
CI
O
+
HCI Br2 / Fe H
6.2 MeO OH CI –S Me
(1) (2) (3)
O
The major product is
Br Br Br
(A) MeO (B) MeO OH (C) MeO (D) MeO OH
Br
6.3 The product is :
OH
O
||
O product.
||
O
O

O
O O
O

(A) (B) O (C) O (D) None

OH
O O O
OH O

OH Me

Ph C C Ph AgNO3
6.4
Me I
 Major product is
OH NO3 Me Me

(A) Ph C C Me (B) Ph C C Me (C) Ph C C Me (D) None of these

CH3 Ph O O Ph
Ph

CH3

6.5 Me3C–CI Ph–COCI Br2 / AICI3

AICI3 AICI3 Product is

Me O Me O Me O Me O
C –Ph Br C –Ph C –Ph C –Ph
(A) (B) (C) (D)
Br

C(Me)3 Br C(Me)3

6.6 Why does the reaction produce stable salt?

HCI + OH –
O CI

A
Because
(A) In 'A' the ring is aromatic
(B) 6 p electrons are present
(C) Ring in a is stabilised by closed loop conjugation
(D) All of these

6.7 The major product of reaction

O
C O

HNO3 + H2SO4

OMe
O O O O
C O C O C O C O
NO2
(A) (B) (C) (D)
NO2 NO2
OMe NO2 OMe OMe OMe
6.8 The end product of the folloowing reaction sequence is:
OCH3
|| O
Dry. AICI3 Zn – Hg / HCI SOCI2 / Pyridine
+ O

OH (tautomerises) Dry. AICI3

H2O
 OCH3OH OCH3 OH
OH CH3O OH CH3O
(A) (B) (C) (D)

6.9 The end product of following reaction is

CH3COCI / AICI3 C2H5COCI / AICI3 CIO

(1) (2) (3)

COO
(A) O = C (B) OOC C – C2H5
C2H5
O
(C) COO (D) OOC COO
C
||

O C2H5
6.10 The product of the followiing reactions is
O
O ||
|| CH3 – C – CI
C CH3
AICI3
O O
|| ||
(A) C – CH3 (B) C – CH3

C=O C – CH3
CH3 O
O O O
|| ||
(C) C – CH3 (D) H3C – C C – CH3

H3C – C
O

6.11 Which of the following is best sequence of reagents for the conversion of
CH3

Br
Br2 / Fe conc. H2SO4 CH3CI / AICI3 H3O
(A)

CH3CI / AICI3 conc. H2SO4 Br2 / Fe H3O

(B)

CH3CI / AICI3 3CI2/ h Br2 / Fe Zn / HCI

(C)
HNO3 + conc. H2SO4 CH3CI / AICI3 Sn / HCI NaNO2 / HCI CuBr
(D)

6.12 The intermediate product 'X' of following synthesis is identified as :

CI2/FeCI3 conc. H 2SO4 Fuming HNO 3 NH3/Cu2O/ dil.H 2So4,
'X' 2, 6-Dinitroaniline
120°C 100°C
 CI CI
CI O2N SO3H HO3S NO2
(A) (B) (C) (D)
HO3S NO2 CI O2N NO2
NO2 SO3H SO3H
6.13 The major product of the following reaction sequence will be
PhCOCI / Pyridine CH3COCI/AICI3 Zn – Hg / HCI / Br2/Fe
OH
(1) (2) (3) (4)

(A) CH3CH2 O C (B) H3C–CH2 O C

O O
Br Br
CH2 – CH3
(C) Br O C (D) CH3 – CH2 O – CH2

O Br
6.14 In the following reactions X, Y and Z are respectively :
NH2

(x) H2/Ni Br2/KOH,

(Z)

OMe
NaNH2/NH3(l)
(Y)
X Y Z
CH = NOH CONH2

CI
(A) , ,
OMe
OMe OMe
NO2 CI CONH2

(B) , ,

OMe OMe OMe

CONH2 CN NO2
(C) , ,

MeO MeO MeO

–
CN COO NH4 CI

(D) , ,
OMe

OMe OMe
 NH2
+
6.15 CH3COCI Br2 + H2O H3O
A B C

C (major product) is

NH2 NH2 NH2

Br
(A) (B) (B) (D) none of these
Br
Br

6.16 Which of the following is regenerated at the end of the reaction

(C2H5)2SO4 / NaOH Sn / HCI NaNO2 / HCI C6H5OH

p – Nitro phenol (Y)
(X) (1) (2) (3) (4)

HI NaNO2 NaNO2/ HCI Sn / HCI NaOH / C2H5Br

(?) (W) (Z)
(9) CuNO2 (7) (6) (5)
(8)

(A) X (B) Y (C) Z (D) W

6.17 Consider the following reaction sequence

HNO3+H2SO4 Sn+HCI NaNO2+HCI Cu2(CN)2+HCN H2O

Product
(6H)
Product is:-

CH2OH CN COOH NH2

CN
(A) (B) (C) (D)
OH
6.18 The products R and S are respectively

NO2 KMnO4/ OH / Br2 / Fe

(X) (W) (R)
Sn/HCI
KMnO4/ OH / Br2 / Fe
(Y) (Z) (S)

NH2
HOOC Br HOOC HOOC Br
(A) and (B) : R and S are same products
HOOC HOOC HOOC
Br
NO2 NO2 NO2
HOOC HOOC Br HOOC HOOC
(C) and (D) and
HOOC Br HOOC HOOC Br HOOC
Br
6.19 The end product 'Z' of the reaction sequence is
CI
AICI3 Zn/Hg Se/
CI O X Y Z
Conc. HCI

(A) (B)

(C) (D) Both A and B

6.20 NO2

+
H3O NaOH+CaO
KCN/C2H5OH A C. Product 'C' is
distilation

Br

COONa NO2
COONa
(A) (B) (C) (D) None of these

Br Br

NH2
HNO2
A B, Product 'B' is
6.21
NH2

+ –
N2 CI N
(A) (B) N
N

N H

(C) N (D) All of these

N

H
 SECTION - II : MULTIPLE CORRECT ANSWER TYPE

(1) Sn/HCI
NO2 'x'
(2) KMnO4

B A
6.22
KMnO4
'y'
[O]

'x' and 'y' are respectively :

NO2 NH2
COOH COOH COOH COOH
(A) B and A (B) A and B
COOH COOH COOH COOH

NH2 NO2
COOH COOH COOH COOH
(C) A and A (D) B and B
COOH COOH COOH COOH

6.23 Which of the following electophilic substitution reaction represent correct product.
NO2 NO2

(A) Br2/FeBr3 Br

OCH3 OCH3

Br
(B) Br2/FeBr3

O O O O

COOCH3 COOCH3

Br2/FeBr3
(C) OCH3 OCH3

Br

(D) C–CH3 Br2/FeBr3 C–CH3

O O
Br
6.24 Which of the followning reactions give alkylation product:
OH

(A) + H (B) + H

AICI3 AICI3
(C) + CH3COCI (D) + Me3C – COCI
6.25 The following conversion reafction can be carried out by using reaction sequence/s.
O O COOH
OH

+
Zn / Hg / HCI, Br2 / h KCN H3O,
(A)
NaBH4 AI2O3, O3 / H2O (oxidative)
(B)
+
Heat I2/NaOH, H
(C)

(D) KMnO4 / OH / heat

6.26 Which of the following ion will be aromatic in nature?
CI N
(A) (B) H (C) (D)
H +
N N
| H H
H
SECTION - III : ASSERTION AND REASON TYPE
6.27 Statement-1 : Benzene and ethene both give reactions with electrophilic reagents.
Statement-2 : Benzene and ethene both have loosely bound  electrons, which can be donated
to vacant orbital of the electrophile.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1.
(C) Satement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.
6.28 Statement-1 :
H H

C is less Acidic than C

(Fluordane)

(Triphenylmethane)
Statement-2 : coplanar arrangement of three rings in fluordane, allows more extensive
delocalisation in conjugate anion.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1.
(C) Satement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.

6.29 Statement-1 : Polycylation in benzene does not occur during friedel Craft's acylation.
Statement-2 : As the product ketone is much more reactive than starting material.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1.
(C) Satement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.
AIBr3
6.30 Statement-1 : Ar C(CH3 )3 Br2   ArBr   CH3 2 C  CH2

 but AIBr
ArCH2 CH3 Br2  3
 o,p – BrC6H4CH2CH3

Statement-2 : In the first case ipso substitution takes place in which Br displaces (CH3)3C+, a
stable cation but removel of CH3CH2 cause large amount of energy.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1.
(C) Satement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.

6.31 Statement-1 : 1, 3, 5 trihydroxybenzene reacts with NH2OH togive oximino derivative where as
1, 3 dihydraxy benzene do not
O NOH OH
||
Statement-2: Former exist in O
which gives NOHwhere at later exists in
||

O NOH OH

no substantial keto form is present which can give oximino derivative

(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1.
(C) Satement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.
SECTION - IV : TRUE AND FALSE TYPE

6.32 The product of reaction of with conc. H2SO4 is

CH2 – OH

4
3
6.33 The best position for ArSE in pyridine 2 is 4
N
1

SECTION - V : COMPREHENSION TYPE

Comprehension # 1
COOH

SOCI2 Solid N2O5 (CH3)2 CuLi Fe / H (i) NaNO2 / H

Q R S T (U)
(ii) PhOH / OH
6.34 The product U is
CH3 O
||
(A) C (B) H3C – C N=N OH

H N=N OH

N=N OH
(C) (D) N=N OH
H3C – C
O CH2CH3
6.35 S on reaction with CI2/ NaOH or on reaction with CI2/ NaOH followed by acidification will not give
which of the followong
NO2 NO2 NO2

(A) (B) (C) CHCI3 (D)

COONa CH2COONa COOH

6.36 T on reaction with NaNO2/HCI followed by reaction with H3PO2 will give.
CH2COCH3 COCH3 COCH3 COCH3

(A) (B) (C) (D)

OH
CH3

Comprehension # 2
The compound C8H9CI (A) on treatments with KCN followed ny hydrolysis gives C9H10O2 (B).
Ammonium salt of B on dry distillation yields C. Which reacts with alkaline solution of bromine
to gives C8H11N. (D) Another compound E (C8H10O) is obtained by the action of nitrous acid on
D. or by the action of aquous potash A. E on oxidation gives F (C8H6O) Which gives the inner
anhydride G on heating.
6.37 The compound A is
CH2 – CI CH2 – CI
CH2 – CI
CH2 – CH2 – CI
(A) (B) (C) (D)
CH3 CH3
CH3
6.38 The compound D is reacts with CHCI3 + NaOH gives a compound H. The structrure of H.
CH2 – CH2 – NC CH2 – NC
(A) (B)
CH3 CH3

CH2 – CN
CH2 – NH – CH3
CH3
(C) (D)
CH3
6.39 The compound A on reaction with AgCN gives.
(A) co,pound H. (B) Compound B (C) compound G. (D) compound D
Comprehension # 3
CH2 – CO
AICI3 Zn(Hg) HCI/ SOCI2
O C10H10O3 (C10H12O2)
(1) (2) (3)
CH2 – CO (X) (Y)

(Z) (C10H11OCI)

Pt, heat H2SO4 / H2 / Pt AICI3

(C10H8) + H2 (C10H10) (C10H12O) (C10H10O)
(7) (6) (5) (4)
(T) (S) (R) (W)
6.40 What product will be obtained if 'W' is treated with C6H5MgBr followed by D3O and then by
heating?

(A) (B)
Ph
OD OD

(C) (D)

Ph Ph
6.41 What product is obvtained when (X) is heated with conc. H2SO4

O O O O
O
(A) (B) (C) (D)

O O O
6.42 What product is obtained when W is heated with KMnO4 / OH.

COOH
COOH
(A) (B)
COOH
COOH
O

(C) O (D) O

SECTION - VI : MATRIX - MATCH TYPE

6.43 Match the following

Column - I Column - II
:e

(A) (p) Anti aromatic

e:

(Non-Planar)

(B) (q) Aromatic

:e
(C) (r) Non aromatic

(Planar)

(D)
(s) G.F = CnHn

(Planar)
6.44
NO2
(1)Sn/HCI
(2) (CH3CO)2O HNO3 Dil.
A B C
H2SO4 H2SO4
Br2
(1) CuBr
H3PO2 (2)Sn/HCI NaNO2
G F (3) NaNO2, HSO4 E D
H2SO4

HBF4,

H
Write the correct combinations

Column-I Column-II
Br

(p) Br Br
(A) A

Br
(q) Br Br
(B) B

NHCOCH3

(C) G

(r)

NO2

NHCOCH3
(s)
(D) H
6.45 Match the correct properties of compounds of column I with column II.

(I) (II)

O–CH=CH2
(A)
(p) Gives Benzoic acid with hot alkaline KMnO4

CH=CH2
(B) (q) o/p directing and activating for E

CH–CH3
(C) (r) Gives fastest reaction with an electrophile
OH

O
C
(D) CH3 (s) Gives an ester on reductive ozonolysis

SECTION - VII : SUBJECTIVE ANSWER TYPE

SHORT SUBJECTIVE:
NO2

(C2H5)2SO4 Zn/HCI/ NaNO2, HCI Phenol Br2/H2O

6.46 (I)
(2)
(II) (III) (IV) (V)
OH (1) 5°C (3) NaOH (4) (5)
OH
The steps involved in the above reaction can be arranged as.
Electrophilic substitution = step (w)
Nucleophilic substitution=step (x)
Reduction reaction = step (y)
Diazocoupling reaction = step (z)
Assign the correct numbers to the type of reactions as follows w x y z
6.47 Observe the following reaction sequence
(1)
NaOH (1 eq) HCN, HCI/AICI3 NH2–NHPh
Phenol (X) (Y) (Z)
Me (3) (4)
(2) D I

H
Answer the following questions in the given format :

P Q R S
P = Number of organic products formed in step-1
Q = Number of organic products formed in step-2 (singnificant products)
R = Number of organic products formed in step-3 (singnificant products)
S = In which step aromatic electrophilic substitutiion has taken place
6.48 CH3CI/AICI3 Br2/h (1 eq.) Na/ether
(1) (2) (3)
(4) Br2/h (1 eq.)
(monobromination)

(5) alc.KOH
(i) O3
(P)
(2 moles) (ii) Zn/CH3COOH

Find the structure formula and molecular weight 'P'.

6.49 Indicate the most probable sites for ArSE reactions.

(A) C O (B) NO2

1 2 1 2

NO2

(C) CH2
(D)
1 1 2 3
2

NHCOCH3

NH
(E)
NH O

O
||
C AICI3/ Na/C2 H5OH
CI A B C
6.50 + (CH2)2 C CI
|| Se/
O
Find the molecular weingt of the compound C and D.

6.51 In the following sequence of reaction how many nucleophilic substitution taking place.
OH O
SOCI2 alc.KOH CI –C – CI CH3MgBr HBr
AICI3
H