Exercise 1

Page # 6 AROMATIC COMPOUNDSE
Exercise - I (Only one option is correct)

Single Choice Questions :
NO2 NH2
NO2
Nitrating
(A) (B)
1. Mixture
Given reaction is an example of

CF3
(A) Substitution electrophilic aromatic (SEAr)
(B) Substitution nucleophilic aromatic (SNAr) (C) (D) All of these
(C) Electrophilic addition reaction (EAR)
(D) Bi molecular nucleophilic substution (SN2)
6. Most reactive towards nitration reaction (Sub-

stitution electrophilic aromatic)
E – Nu
2.
NH2
Name of intermediate produced during given (A) (B)

reaction will be
(A) Arenium ion
(B) -complex/wheeland intermediate O
(C) Nonaromatic cyclohexa dienyl carbocation
NH N
(D) All of these
(C) (D)
3. Which of the following reagent is best when
friedel craft Halogenation takes place
(A) HO– (B) AlCl3 (anhyd.)
(C) AlCl3 (hydrated) (D) All of these
7. Which of the following compound gives ben-
zoic acid when it reacts with hot KMnO4 fol-
4. WHat is the name of electrophile when ben- lowed by acidification.
zene goes nitration
(A) Nitrosonium ion (B) Nitronium ion
(C) Halonium ion (D) Alkyl carbocation (A)
O H
5. Which of the following compound gives poor CH 3
yield in friedel-craft reaction
(B) (C)
(D) All of these
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AROMATIC COMPOUNDS Page # 7
CF3 O
Conc. HNO 3
8. + Major product 11. + AlCl3
O  
Conc.H2SO4
CF3 CF3 O
NO2 Zn(Hg)
(A) HCl
  (B) 
conc.H2SO4
   (C) (Major prod-
(A) (B)
uct)
NO2 C will be :
CF3
(A) (B)
(C) (D) A and C both
O
NO2
OCH3
(C) (D)
O
9. Nitration Major product
12. How many  electron are there in the follow-

F ing speices :
OCH3
OCH3
NO2
(A) (B)
NO2
(A) 2 (B) 4
F (C) 6 (D) 8
(C) Mixture A and B F of these
(D) None
13. Ease of ionization to produce carbocation and

NH2 bromide ion under the treatment of Ag will be
maximum in ?
NaNO2 H 2O
10. (A) (B)
2HCl Boil O
Product (B) will be : (A) (B)

OH
Br
Br
(A) (B)
+ –
N2Cl Cl (C) (D)
(C) (D) Br Br

Cl In which cases N O2 will attack at meta posi-
14. 2SbCl5 tion
   P ; P will be
Cl
(A) II and IV (B) I, II and III
(C) II and IV (D) I only
(A) 2– (B) 2+ 2SbCl6–

18. Increasing order of the following for electrophile
substitution reaction as -
(C) (D) Mixture of A & B

(I) CH3 (II)
15. Which order is correct for the decreasing re- (III) COOH
activity to ring monobromination of the fol-
lowing compounds : (A) I > II > III (B) III > II > I
(I) C6H5CH3 (II) C6H5COOH (C) II > III > I (D) I > III > II
(III) C6H6 (IV) C6H5NO2
(A) I > II > III > IV (B) I > III > II > IV 19. Which of the following will form tri-bromo de-
(C) II > III > IV > I (D) III > I > II > IV rivative of phenol ?
OH OH
16. Which of the following order is correct for the
decreasing reactivity to ring monobromination Br2 Br2
(A)   (B)  
of the following compounds : HO 2 H2O
CH 3 COOH
(I) (II) OH OH
Br2 Br2
(C)   (D)  
COOH NO2 CS 2 H2O
(III) (IV)
Ph
(A) I > II > III > IV (B) II > III > IV > I
(C) I > III > II > IV (D) III > I > II > IV HBF4
20. Ph O–Ph   Product of this
 Ph
17. Electrophile N O2 attacks the following : reaction is :
CCl3 NO2 OH
Ph
(I) (II)
(A) Ph H+
CHO O Ph
(III) (IV)
OH 23. Benzene reacts with n-propyl chloride in the

Ph presence of anhydrous AlCl3 to give predomi-
nantly :
(B) + Ph OH
(A) n-Propylbenzene
(B) Isopropylbenzene
Ph
(C) 3-Propyl-1-Chlorobenzene
Ph
(D) No reaction
(C) Ph OH +
24. In the sulphonation, acetylation and formylation
Ph of benzene the group of effective electrophiles
Ph would be :

Ph OH (A) SO3+, CH3C  O+, H C O
(D)
Ph 
(B) SO3, CH3 –C  O+, H C O
(C) SO3, CH3CHO, CO + HCl

NO2 (D) HSO3, CH3CO, HCO
(1)NaOH
21.    (A), Product (A) is
(2)H3O 25. p-Nitrotoluene on further nitration gives :
I
Br CH3
CH3
NO2
NO2
NO2
(A) (B)
NO2
(A) (B) NO2
OH NO2
I
Br
OH
OH NO2 CH2OH CH3
OH NO2 NO2
(C) (D)
(C) (D)
I I O2N
Br Br NO2
22. For preparing monoalkyl benzene, acylation

process is preferred than direct alkylation be- 26. The major product formed on monobromination
cause of phenylbenzoate is :
(A) In alkylation, a poisonous gas is evolved

Br
(B) In alkylation, large amount of heat is evolved
(C) In alkylation, pollyalkylated product is O
formed (A)
O
(D) Alkylation is very costly
28. The major product formed in the reaction is :
OMe
3 AlCl
O + (CH3)2 CHCH2Br 
Br
(B)
O
OMe
(A)
CH 2CH(CH 3) 2
Br
OMe
O
(B)
(C) (CH3 )2CHCH2
O
OMe
(C)
C(CH 3) 3
OMe
O
(D) (D)
O (CH3 )3 C
Br
29. In the sulhponation of benzene, the active elec-

27. The major product formed in the reaction is : trophilic species is :
(A) SO2 (B) SO3
+ (C) SO42– (D) HSO4–
OCH3 + E
(electrophile)
30. Which one of the following compounds under-
goes bromination of its aromatic ring at the
(A) OCH3 fastest rate ?
E
(A) (B)
(B) E OCH3
N
|
H
OCH3
(C)
E NH
(C) (D)
NH
OCH3 O
(D)
E 31. In the reaction the major product formed is :
O
Br2 (1mole)
N    
Fe
O 33. Increasing order of rate of reaction with Br2/

Br AlBr3 is :
(A) N OCH3 OCH3
O
(I) (II)
N
(B)
O OCH3
Br
O
O
(III) (IV)
N
(C)
(A) III < I < II < IV (B) III < II < I < IV
(C) II < IV < III < I (D) IV < II < III < I
Br
O
34. What combiantion of acid chloride or anhy-
(D) N Br dride and arene would you choose to prepare
given compound ?
32. HNO3 / H2SO4

   (A) Ma-
MeO C–CH2–CH2–CO2H
jor product : O
NO2
NO2 O O
(A) AlCl3
(A) + Cl–C–CH2–CH–C–Cl
MeO
CH3
NO2
(B)
O
MeO
(B) + AlCl3
O  
NO2
(C) O
MeO
O
(D)
NO2 (C) + AlCl3
MeO O  
37. Which of the following is most reactive toward

O SNAr :
(D) + AlCl3
  Cl Cl
NO2
O
(A) (B)
NO2 NO2
35. Which position will be attacked most rapidly
+
by the nitronium ion (NO2 ) when the com-
pound undergoes nitration with HNO3/H2SO4 :
Cl
(I) (II) (III) (IV) Cl
O2N NO2
H 2C
OCH3 (C) (D)
H3 C
NO2
NO2
(A) I (B) II
(C) III (D) IV
Cl
36. Identify (C) in the reaction(s)
HNO3 CH3ONa
CH3 38.   (A)   (B) Major,,
 
NaNO2 / HCl

H O, 
  (A) 2 Cl
0C Product (B) is
Cl Cl
NH2
(i)CHCl ,KOH, 
(B)   3   (C) (A)
NO2
(B)
(ii)dil.HCl OCH3
OCH3 Cl
CH3 CH3 OCH3 Cl
H3
CHO OC
(A) (B)
(C) (D)
CHO NO2 NO2
OH OH Cl Cl
CH3 39. The major product formed in the reaction is :
(C) (D) None of these

CHO
conc.H2SO4
+ HNO3    
Cl
(A) Lindane (B) DDT

NO2 (C) Caprolactum (D) Nylon-6
(A) (B)
NO2 AlCl3
43. C6H6 + A   C6H5CONH2
A in the above reaction is :

NO2 (A) NH2CONH2 (B) ClCONH2
(C) CH3CONH2 (D) CH2(Cl)CONH2
(C) (D)
CH3COCl ZnHg
NO2 44. C6H6 AlCl
  A    B
3HCl
The end product in the above sequence is :

40. CrO2Cl2
C6H5CH3  H2O
  A   B
 (A) Toluene (B) Ethyl benzene
The functional group present in B and name of (C) Both the above (D) None
the reaction would be
(A) –CHO, Gattermann aldehyde synthesis
(B) –CHO, Etard reaction
45. AlCl3
+ CH3–CH2–CH2–CH2–Cl 
(C) –COCH3, Fridel Crafts reaction 
(D) –CHO, Oxo reaction
hydrocarbon (X) major product X is
41. Which chloroderivative of benzene among the
following would undergo-hydrolysis most
readily with aq. NaOH to furnish the corre- (A) CH2CH–CH3
sponding hydroxy derivative.
CH3
NO2
CH3
(A) O2N Cl
(B) C–CH3
NO2
CH3
(B) O 2N Cl
(C) CH2CH2CH2CH3
(C) Me2N Cl (D) None of correct
46. Reaction of SO3 is easier in :

(D) Cl
(A) Benzene (B) Toluene
(C) Nitrobenzene (D) chlorobenzene
Cl conc.H SO4
47. The mixture of the following four aromatic com-
42. Chloral +   2   prod- pounds on oxidation by strong oxidising agent
gives :
uct. The produt is :
CH3 C2H5
Ni,High temp.
52. + H2      (A). Which of
high pressure
the following can be isolated as the product

of this reaction.
CH2 OH CHO
and (A) (B)
(A) Mixture of C6H5CH2OH+C6H5COOH

(B) Mixture of C6H5CHO + C6H5COOH (C) (D)
(C) C6H5COOH
(D) None of the above
53. Which of the following is/are produced when a
mixture of benzene vapour and oxygen is
48. Methyl group attached to benzene can be passed over V2O5 catalyst at 775 K ?
oxidised to carboxyl group by reacting with :
(A) Oxalic acid (B) Glyoxal
(A) Fe2O3 (B) AgNO3 (C) Fumaric acid (D) Maleic anhydride
(C) KMnO4 (D) CrO3
54. Which of the following is the least reactive in

CH=CH2 the case of bromination ?
(A) Phenol (B) Aniline
Br2 (C) Nitrobenzene (D) Anisole
49. A 
CCl
KMnO4 / 
   B
4
Compound A and B respectively are : F

55. Above compound undergoes
(A) o-Bromostyrene, benzoic acid
(B) p-Bromostyrene, benzaldehyde NO2
(C) m-Bromostyrene, benzaldehyde

(A) SN1
(D) Styrene dibromide, benzoic acid
(B) SN2
(C) Elimination
50. The number of benzylic hydrogen atoms in (D) Nucleophilic aromatic substitution
ethylbenzene is :
(A) 3 (B) 5
56. Benzene on reaction with ‘A’ forms
(C) 2 (D) 7
O
51. The highest yield of m-product is possible by

the electrophilic substitution of the which on reaction with
following :
(A) C6H5CH3
(B) C6H5CH2COOC2H5
(C) C6H5CH(COOC2H5)2 ‘B’ forms ‘A’ and ‘B’ are:
(D) C6H5C(COOC2H5)3
61. Ring nitration of dimethyl benzene results in

O
the formation of only one nitro dimethyl ben-
(A) Zn (Hg) + conc. HCl, zene. The dimethyl benzene is :
Cl
O CH3
(B) , LiAlH4 CH3
Cl (A) (B)
CH3
CH3
O
(C) , NaBH4 CH3
Cl
O (C) (D) None of these
(D) , Zn(Hg) + conc.HCl
Cl
CH3
+ AlCl3
62. if p-methoxy toluene is nitrated, the major
57. In a reaction of C6H5Y, the major product product is :
(>60%) is m-isomer, so the group Y is : CH3 CH3
(A) –COOH (B) –Cl
(C) –OH (D) –NH2 NO2
(A) (B) NO2

58. Which of the following will undergo sulphonation
at fastest rate ? OCH3 OCH3
CH3NO2
(A) (B) (C) (D) No reaction
OCH3
63. An aromatic compound of molecular formula

(C) (D) C6H4Br2 was nitrated which gives three iso-
mers of formula C6H3Br2NO2 were obtained. The
original compound is :
59. Which of the following is most reactive to- (A) o-dibromobenzene
wards sulphonation ?
(B) m-dibromobenzene
(A) m-Xylene (B) o-Xylene
(C) p-dibromobenzene
(C) Toluene (D) p-Xylene (D) both A and C
60. When sulphonilic acid (p-H2NC 6H4SO 3H) is N

treated with excess of bromine water the prod-
uct is: 64. + Ph – N2+Cl–  (A) major product A
(A) tribromo product
(B) dibromo product will be
(C) monobromo product
(D) tetrabromo product
67. For the electrophilic substitution reaction in-

N
N volving nitration, which of the following se-
quence regarding the rate of reaction is true ?
N = N – Ph
(A) (B) (A) K C6H6  K C6D6  KC6 T6
N = N – Ph (B) K C6H6  KC6D6  K C6 T6
N N
(C) K C6H6  K C6D6  KC6 T6
(D) K C6H6  K C6D6  K C6 T6

(C) (D)
Ph Cl 68. For the electrophilic substitution reaction in-

volving sulphonation, which of the following
seqence regarding the rate of reaction is true
65. Which of the following carbocations is expected
to be most stable ?
(A) K C6H6  K C6D6  KC6 T6
NO2 NO2
(B) K C6H6  KC6D6  K C6 T6
+
(C) K C6H6  K C6D6  KC6 T6
(A) (B)
+
(D) K C6H6  K C6D6  K C6 T6
H Y H Y
NO2 NO2
+ H 69. WHich of the following structures correspond
(C) Y (D) to the product expected, when excess of C6H6
H reacts with CH2Cl2 in presence of anhydrous
+ Y
AlCl3 ?
Cl
66. Which of the following species expected to
have maximum enthalpy in an electrophilic aro- (A) CH
matic substitution reaction ?
H E
(B) CHCl2
(I) + E+  (II) 
Cl
H E H E C
(C)
(III)  (IV)  Cl
(D) CH2
E
(V)
70. Identify the correct order of reactivity in elec-
trophilic substitution reactions of the follow-
(A) Species (II) (B) Species (III) ing compunds:
(C) Species (IV) (D) Species (V)
C2H5 CH3
|
(1)CH3  C H  CH2Cl / AlCl3
(C)         
(2)HNO3  H2SO 4
(I) (II)
(1)HNO  H SO
 CH3 
2 4

 
Cl (D) 3
NO2 |
(2)CH3  C H  CH2Cl / AlCl3
Cl NO2
(III) (IV)
73. Which of most reactive towards nucleophilic
aromatic substitution.
(A) I > II > III > IV (B) IV > III > II > I
(C) II > I > III > IV (D) II > III > I > IV F F
(A) (B)
71. Conjugation of electron withdrawing groups,
O O
CH3 NO2
e.g., –CHO, – C – R , – C – OR , –C  N, –
NO 2 activates nucleophilic attack in Cl I
halobenzene. The order of reactivity of these
group towards nucleophilic aromatic substitu-
tion. (C) (D)
O O O NO2 NO2
(A) –NO2 > –C  N > –C–H > – C – R > – C – OR
O 74. Which is the best synthesis of

O O
(B) –C–H > – C – R > – C – OR > –C  N > –NO2 CH3O NO2 ?
O O O NO2
(C) –C  N > –NO2 > –C–H > – C – R > – C – OR

Br2 HNO3 HNO
3
(A)        
FeBr3 H2SO 4 H2SO 4
O O O
NaOCH
3
   
(D) –C–H > –NO2 > –C  N > – C – OR > – C – R CH3OH
HNO
3 HNO
3 Br2
(B)        
72. Choose the best method to prepare given com- H2SO 4 H2SO 4 FeBr3
pound :
NaOCH
3
   
CH3OH
H3C
H3C NO2 HNO Br HNO
3 2 3
(C)         
H3C H2SO 4 FeBr3 H2SO 4
NaOCH
3
   
CH3OH
(1)HNO3  H2SO4
(A)   
(2)Me3CCl / AlCl3
HNO
3 2 3 Br NaOCH
(D)          
H2SO 4 FeBr3 CH3OH
(1)Me3CCl / AlCl3
(B)      

(2)HNO3  H2SO4 HNO
3
  
H2SO 4
75. The cumulative effect of their fluorine acti- (A) Statement-1 is true, statement-2 is true
vate the rings of penta and hexa fluorobenzene and statement-2 is correct explanation for
toward nucleophilic aromatic substituiton. What statement-1
is compound X in the following
(B) Statement-1 is true, statement-2 is true
synthesis ?
and statement-2 is NOT correct
explanation for statement-1
F
(C) Statement-1 is true, statement-2 is false
F F (D) Statement-1 is false, statement-2 is true
HOCH2 CH2OH K2CO3
     (A)   
 (X) (C8H4F4O2)
F F NaOH,  
77. Statement-1 : Rate of nitration is C6H6 ~ C6D6

F ~ C T
6 6
Statement-2 : Formation of wheland inter-

F mediate is rate determining step in nitration of
F O CH = CH2 benzene, not the breaking of C–H or C–D bond.
(A)
(A) Statement-1 is true, statement-2 is true
F OH and statement-2 is correct explanation for
statement-1
F
(B) Statement-1 is true, statement-2 is true
F
and statement-2 is NOT correct
F OCH2CHO explanation for statement-1
(B) (C) Statement-1 is true, statement-2 is false
F H
(D) Statement-1 is false, statement-2 is true
F
CARBENE
F
78. The orbital picture of a singlet carbene (:CH2)
F O can be drawn as
(C)
F O p
H
F (A)
C
F 2
H sp
F O
(D) CH3
p
F O H
(B)
F C
2
H sp
76. Statement-1 : Nitro benzene reacts with

py
O pz
Me – C – Cl , AlCl 3 to produce
(C)
m-nitroacetophenone. C H
Statement-2 : NO2 group attached to the ring
is a meta directing during SE. H
(D) none of these
79. The orbital picture of a triplet carbene can be O–

drawn as
+ :CCl2 
p
H
O– O OH
(A) O
C CHO CHO
CHCl2
H OH H
+
2
H sp CCl2
o-product is major product because :

(i) There are two o-positions available as com-
py pared to one para.
p pz
H (ii) o-product is more stable due to the forma-
H
tion ofsix membered chelate formation.
(B) C (C) C
sp
2 Na
H
H O O
C–H
(D) none of these
Question No. 80 to 82 (3 questions) If 1° amines (aliphatic and aromatic) react with

DCC in basic medium it yield isocyanide or
It is believed that chloroform and hydroxide
carbylamine. The reaction is known as
ion react to produce an electron deficient in-
carbylamine reaction.
termediate dichlorocarbene : CCl2 (DCC)
H H
Cl Cl Cl
| |
: C—Cl  R–N – CCl  R – N – C – Cl
OH– + H— C—Cl Fast
H 2O + R–N:+CCl2 2
| |
Cl Cl H H H
H
Slow
: CCl2 + Cl–
 R – N = C – Cl + Cl–
Treatment of phenol with DCC in basic medium
H H
introduces an aldehyde group, onto the aro-
matic ring. This reaction is known as Reimer
Tiemann reaction.
OH OH OH
–
CHO –H 2O OH –
(i)OH
+
+
(ii):CCl2,(iii)H
Phenol –
CHO R – N = C – Cl   OH
The Reimer-Tiemann reaction involves electro- H

philic substitution on highly reactive phenox- +
ide ring The electrophilic reagent is dichloro
The product is known as isocyanide & it is a
carbene :CCl2.
foul smelling substance.
80. Step marked by * is : Br Br

F F
(A) Aromatization reaction CH3 CH3 CH3 H
(B) intramolecular acid base reaction
(A) (B)
(C) both of the above
(D) none of the above
H H H CH3
F F F F
H CH3 CH3 CH3
OH
(C) (D)
81. If is used instead of during
CH3 H H H
Reimer Tiemann reaction the product formed

O
is :
Ag2O
84. Ph – C – CHN 2   (A); product (A)
14 HO
2
Cl Cl is:
CHO (A) Ph– 14CH2 – CO2H
(B) Ph– CH2 – 14CO2H
(A) (B)
(C) Ph– 14CO2H
(D) Ph– CO2H
OH 85. Which of the following wil not give carbylamine

reaction
(C) (D) (A) t-butly amine
(B) aniline
(C) sec. butylamine
CHO (D) N-methyl methanamine
82. If CCl4 is used in place of CHCl3 during Reimer

OH
Tiemann reaction, the product formed is:
(i) CHCl3 / KOH

OH 86.    (A) Product (A) will
OH (ii) H
Cl CHO
(A) (B) CH3
be
OH OH
OH OH
CCl3 COOH (A) (B)
(C) (D) CHO
CH3 CHO
OH OH
CHO
83. CHF 2 Br OH– (A) [Intermediate]
 
 (C) (D)
Trans 2 butene
 (B)
     
CH3 CH3
in this reaction B is :
I
O Na OH
Ph Ph EtOK HBr
87. PhCHCl A   B  

EtOK
C (A) (B)
correct presentation of C is : O Na OH
CO2H
CO2H
Ph I Ph OEt
(A) (B) OH OH
Ph Ph Ph Ph
(C) (D)
Ph Ph Cl OH
CO2H
OH
(C) Br (D)
Ph Ph Ph Ph
90. Intermediate produced during reimer tiemann’s
formlylation will be
(A) :CCl2 (B) :CH2
F ..
88. MeOK
+ CH – Cl   ? (C) CCl3 (D) CHCl3
Br
F 91. Which of the following compound doesn’t gives

Hoffmann’s carbyl amine test ?
(A)
(A) .. (B) ..
NH NH2
F
(B) NH2
Cl
NH2
(C) (D)
Cl
(C)
Br
Br 92. CH3 – NH2 + CHCl3 + KOH  major product

(D) will be :
(A) CH3 – C  N (B) CH3 – NH – CH3
(C) CH3 – N+  C– (D) NH3
93. What is the product of the following reaction
OH ?
(i) aq. NaHCO3 / boil

89.         (X)
(ii) H3O MeOK in chloroform
      
 ?
OH
Identify unknown (X)
Cl Cl 95. Which of the following will not given Hoffmann

bromamide rection ?
(A) (B)
O
(A) CH – C – NH
3 2
Cl
O
(C) (D) (B) C – NH – Br
Cl
NITRENE O
Comprehension (Q.94 to Q.96) (3 Questions)
(C) C – NH2
Hoffmann Rearrangment:
It involves conversion of a carboxylic acid amide
into an amine with a loss of a carbon atom on O
treatment with aqueous sodium hypobromite.
THus Hoffmann result in shortening of a car- (D) C – NH – CH3
bon chain.
O
Br2
R – C – NH2 NaOH
  R – NH + NaBr +
2
O
Na2CO3
Mechanism of the reaction is – C – NH2 Br2 KOH
96.    A
O H H
NaOH
 
R – C – NH2 (Major)
O Product (A) is :
R – C = NH + Br — Br
NH2
(A)
H H
R – C – NH – Br NH2
OH (B)
H H
O
H2O
Na2CO3 + R–NH2 O=C=N–R R – C – N – Br
NH2
(C)
O HH
C – NH2 Br2
94.   (A) (Major)
KOH
NH2
(D)
H H
Product (A)
(A) Ph–NH2 (B) Ph–CH2–NH2
(C) Ph–NH–CH3 (D) Ph – N (CH3)2
Beckmann Rearrangment:
The given is mechanism of Beckmann
O
rearrangment.
(B)
NH – C – CH3
R +
R
H
C=N C=N
R' (I) R'
OH O—H
O
H
(C)
(II) –H2O NH2–C – H
R'–C = N – R
(III) –H2O
O
O O–H
(IV)
(D)
R'–C – NH – R R'–C = N – R C – NH2
97. Reagent cannot be used in Beckmann rear- O

rangement is \
(A) H2SO4 (B) BF3 C – NH2
(C) SO3 (D) OH–
100. KOBr
 (A)
(A) Ph – CH2 – NH2 (B) Ph – NH2

98. Rate determining step in the Beckmann rear- (C) Ph – CO2H (D) Ph – NH – CH3
rangement is
(A) I (B) II
(C) III (D) IV O
N–H Br2
101.  (A) Product (A) will
KOH
99. C – CH3 H

2SO 4
 (X) . Product O
be
N – OH
(X) is CO2
(A)
NH2
O
CO2
(A)
C – NH – CH3 (B)
CO2
NH2 NH2
(C)
NH2
(D)
102. Give the major organic product of the following

reaction : O
O H 2SO 4
(C) NH
2OH
 (A)   caprolactum
( B)
CF
3CO
3H
 Major
O O
O (D CH3CO3H
CH3O C CH 3O O –C
O
O
O
(A) (B)
105. 2
Na
 (A) Product (A) is
O +
O O
O (A) (B)
+
(C) (D)
+
(C) (D)
O
103. CH
2N2

CH3 – C – CH 3
(X) CF
3CO
3H
 Major Product (Y) is
O
106. 2
Na
 (A) Product
(A)
CH 3 – C – O – CH 3 (A) is
(B)
O –2
(A) (B)
CH 3 – C – O – CH 2 – CH 3
O
(C) +2 (D) All
(C)
CH–
3 CH 2– C – O – CH 3
(D) CH3 – CH2 – CH2 – O – CH3
104. Which of the following reaction represent in-

correct major product.
(A)
O
KOBr
 CH3 – NH2
CH 3 – C – NH – CH 3
OH
O
( i ) O 2 / hv
(B)  
  +
( ii ) H 3O
Cumene

Exercise 1

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Page # 6 AROMATIC COMPOUNDSE

Exercise - I (Only one option is correct)

Given reaction is an example of

6. Most reactive towards nitration reaction (Sub-

Name of intermediate produced during given (A) (B)

(D) All of these

12. How many  electron are there in the follow-

13. Ease of ionization to produce carbocation and

Product (B) will be : (A) (B)

(A) 2– (B) 2+ 2SbCl6–

(C) (D) Mixture of A & B

OH 23. Benzene reacts with n-propyl chloride in the

(C) SO3, CH3CHO, CO + HCl

22. For preparing monoalkyl benzene, acylation

(A) In alkylation, a poisonous gas is evolved

28. The major product formed in the reaction is :

29. In the sulhponation of benzene, the active elec-

O 33. Increasing order of rate of reaction with Br2/

32. HNO3 / H2SO4

37. Which of the following is most reactive toward

CH3 39. The major product formed in the reaction is :

(C) (D) None of these

(A) Lindane (B) DDT

A in the above reaction is :

The end product in the above sequence is :

(C) Me2N Cl (D) None of correct

46. Reaction of SO3 is easier in :

the following can be isolated as the product

and (A) (B)

(A) Mixture of C6H5CH2OH+C6H5COOH

54. Which of the following is the least reactive in

Compound A and B respectively are : F

(C) m-Bromostyrene, benzaldehyde

51. The highest yield of m-product is possible by

61. Ring nitration of dimethyl benzene results in

(A) (B) NO2

(A) (B) (C) (D) No reaction

63. An aromatic compound of molecular formula

60. When sulphonilic acid (p-H2NC 6H4SO 3H) is N

67. For the electrophilic substitution reaction in-

N = N – Ph (B) K C6H6  KC6D6  K C6 T6

(D) K C6H6  K C6D6  K C6 T6

Ph Cl 68. For the electrophilic substitution reaction in-

O 74. Which is the best synthesis of

(C) –C  N > –NO2 > –C–H > – C – R > – C – OR

77. Statement-1 : Rate of nitration is C6H6 ~ C6D6

Statement-2 : Formation of wheland inter-

76. Statement-1 : Nitro benzene reacts with

79. The orbital picture of a triplet carbene can be O–

o-product is major product because :

Question No. 80 to 82 (3 questions) If 1° amines (aliphatic and aromatic) react with

The Reimer-Tiemann reaction involves electro- H

80. Step marked by * is : Br Br

Reimer Tiemann reaction the product formed

OH 85. Which of the following wil not give carbylamine

82. If CCl4 is used in place of CHCl3 during Reimer

(i) CHCl3 / KOH

F 91. Which of the following compound doesn’t gives

Br 92. CH3 – NH2 + CHCl3 + KOH  major product

(i) aq. NaHCO3 / boil

Identify unknown (X)

Cl Cl 95. Which of the following will not given Hoffmann

97. Reagent cannot be used in Beckmann rear- O