CHEMISTRY CHAPTER WISE_QUESTIONS

BENZENE(B)

CH 2COCl

CH 2COCl
X ; X is
AlCl3
7.
O
O C
C CH2 CH2

CH2 CH2
Cl C C

1) O 2) O
O
C O
C CH2
CH2

CH2
CH2
C C

3) O 4) O
ANS:1
SOL : acylation does not proceed for multiple Ar SE due to – M effect
Paragraph for Questions 33 and 34
I

1 M g / E t2O 1 . P B r3 1 . S O C l2
A B C
O 2.SnCl4 /
2) 2)NaCH COOO t 2

3) H 3O , then
3) H

33. “A” is
OH

O
O
OH

A) B) C) D)
ANS :B

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 I MgI CH 2 CH 2 O Mg I
CH 2 CH 2 OH

Mg / D . E
H

(A)
SN 2 PBr3

Br

SOL:
34. Product “C” is
O
O O

A) B) C) D)
ANS :C
SOL:
Paragraph for Question 35 and 36
Mechanism of ozonolysis is given below
O+ O
O O O
O O+
R1 H O O

R1 C C H R1 C+ C H

R2 R3 R2 R3
R2 R3 mol ozonide
I II III

R1 O H
C C
H
OH LA R2 R3
O O
2

R3 Ozonide
2O

OH
R1 R2
H

O IV
Zn/H2O
R1 C R2 + R3 COOH

R1 C R2 + R3 C O
H
Note : - From II to III other cleavage is also possible. With the help of above
mechanism answer the following questions
35. Total number of ozonides (including stereoisomers) formed when 2 – pentene is treated

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with O3 is
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 A) 3 B) 6 C) 10 D) 12
ANS:C
O
O
O
O
O O
O O
4 O
3 3
SOL: 36. Two C5H8 isomers undergo catalytic
(Pt) hydrogenation to form the same C 5H10 product. On ozonolysis followed by
oxidative work up (H2O2), one isomer gave a C5H8O4 diacid, while the other isomer
gave a C5H8O3 ketoacid. Which of the following isomeric pairs correspond to this
evidence ?
A) Cyclopentene and 1 – pentene
B) cyclopentene and 1 – methyl cyclobutene
C) 1 – methylcyclobutene and 3 – methylcyclobutene
D) cyclopentene and 3 - methylcyclobutene
ANS:C
SOL:
65. Which of the product is obtained in the following reaction :
(i) B 2 H 6 THF
product
(ii) OH , H 2 O 2

CH 3

CH 3 CH 3

H CH 3 H OH
1) OH 2) OH 3) OH 4) H
ANS:1
SOL: Hydroboration followed by oxidation results in the addition a molecule of H 2O
In hydroboration oxidation
Anti markovnikov product is formed
Syn addition
 CH 
CH 2  CH 2  Cl  Dry
Mg  3 
 A CH  B   3 
I 3
CCOCl
Ether 40 0 C

79.
Possible isomeric monochloro products
1) 3 2) 7 3) 5 4) 6
ANS:3
SOL:
22. Which of the following reaction(s) give(s) aromatic compound as product?

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 Br
K (Metal)
2AgBF4
Br H H
A) B)
OH

Anhy.ZnCl2 / Conc.HCl tBuOK / 

Br
C) D)
ANS:ABD
SOL:

The products formed are

21)

A) B) C) D) Both (A) and (B)

ANS:D
SOL:
22) In which of the following case, the rate of Electrophilic Aromatic Substitution will be
faster.

A) B) C) D)

ANS:A
SOL: High hyper conjugation
CH3

Ozonolysis

 Pr oducts;
22.

CH3
The products formed are :
O O O
|| || ||
(A) CH3  C  CHO (B) CHO—CHO (C) CH3  C  C  CH3 (D) HCOOH

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ANS:AB
CH3
O
||
O3
 2CH3  C  CHO  2CHO
|
CHO

CH3
SOL:
Paragraph for Question 33 and 34
Electrophilic substitutions are characteristic reaction of aromatic compounds. In this
reaction hydrogen of the aromatic ring is replaced by an electophile because hydrogen in
the form of H is very good leaving group. —COOH and —SO3H are also good leaving
groups when they are present either at ortho or at para to the highly activating groups
like —NH2 and —OH.
33. Which one of the following compounds will be most unreactive towards electrophilic
substitution reaction?
NO 2 NO 2
CH3 OCH3

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

2N NO 2 OH
ANS:B
SOL: –NO2 group highly deactivate Benzene ring.
34. Benzene sulphonic acid is converted into benzene by
(A) heating with dilute sulphuric acid (B) heating with dilute NaOH
(C) heating with soda lime (D) heating with Zinc dust
ANS:C
SOL: Benzene ring is highly deactivated due to –Cl group.
31. Which of the following groups cannot participate in resonance with benzene ring?
CH3
 

(A)—COCl (B) —N H 3 (C) — C H2 (D) O H

ANS:BD
SOL:
32. Which of the following compound(s) is/are more reactive than benzene towards
nitration?
COOH CH3 OH H3C CH3

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

ANS:BD
SOL:
36. How many of the following groups are activating towards electrophilic aromatic
substitution?

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 O
||
 NHCOR,  OCOR,  C  O  R,  NR 2 ,  NH 2  OH, OR
ANS:4
SOL: –NR2, –NH2, –OH and –OR are considered as strong activators.
38. Number of different products formed in mononitration of 1, 3 – dibromo benzene
including minor products is
ANS:3
Br Br Br Br
NO 2
HNO /H SO

3 2 4
+ +
Br
Br NO 2 Br Br

SOL: NO 2

69. Increasing order of rate of reaction with HNO 3/H2SO4 is:

O O O
O O O O O O
O O O

I II III
A) III < II < I B) II < III < I C) I < III < II D) I < II < III
ANS:D
SOL: Electron releasing groups on aromatic ring activates Electrophillic aromatic substitution reaction
O

+ C Cl 
AlCl3

( X );
79.
O
a) C
b)

H C
c) d)
O
ANS:B
C C


C C C  C C + CO

C O C
SOL:
31) Write the following in decreasing order towards the electrophilic substitution reaction
i  benzene  ii  chlorobenzene  iii  nitrobenzene iv  toluene
1) (i)>(ii)>(iii)>(iv) 2) (iv)>(i)>(ii)>(iii)
3) (ii)>(iii)>(iv)>(i) 4) (ii)>(i)>(iv)>(iii)
ANS:2
SOL:

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32) The electrophile which is considered to be the active agent in the nitration of benzene is
1) NO2 2) NO 3) NO2 4) HNO2

ANS:3
SOL:
33) The conversion
CH2CH2CH3 CH2CH2CH3

Br
Can be best effected using
1) Br2 / CCl4 2) Br2 / H 2O 3) Br2 / Fe 4) Br2 / Benzoyl peroxide
ANS:3
SOL:
34) 1 mole of 50% pure CaC2 on hydrolysis followed by passing through red hot copper
tube, how many moles of Benzene is formed
1 1 1 1
1) 2) 3) 4)
2 5 6 8
ANS:3

SOL: 3 moles of gives 1 mole of . 0.5 moles gives moles of benzene. 0.5 moles of
obtained by the hydrolysis of 1 mole of 50% pure
35) A Friedel-Crafts reaction of excess benzene with chloroform produces
Cl C6 H 5
| |
1) C6 H 5CHCl2 2) C6 H 5  C  C6 H 5 3) C6 H 5  C  C6 H 5 4) all of these
| |
H H
ANS:3

SOL:
37) The major product obtained in the reaction
O

Br2 / FeBr3
C CH2 is expected to be

O O

A) Br C CH2
B)
C CH2 Br

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 O
O

C CH2
C) C CH D)

Br
Br

ANS:2

SOL:
CH3

KMnO4 HNO3 / conc.H 2 SO 4

A B
(Major Product)
38) , the product B is

1)3-Nitorbenzoic acid 2)3-Nitrotoluene

3)4-Nitrotoluene 4)4-Nitrobenzoic acid
ANS:1

SOL:
41) The product formed in maximum proportion in the following reaction is

anhydrous AlCl
CH 3CH 2CH 2Cl 
3

CH3
CH2CH2CH3
CH
1) 2)
CH3

CH3
Cl

CH2CH2CH3 CH3
3) 4)

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CH3

Page 8 of 17
ANS:2
SOL: During formation of most stable in preffered as intermediate which attaches to Benzene.

55) Chlorination of Toluene with an excess of Cl2 in the presence of light and heat gives
product (X) . the compound (X) is heated with Aqueous NaOH and finally acidified to
give a compound (Y). Y is
CH3
CH3
CH3
COOH
OH
1) 2) 3) 4)

OH
OH
ANS:4

SOL:
49.
OH

1.NaOH

2. CH 3OSO2OCH 3
Cl
OH OH
HO3S CH3O3S

(1) Cl (2) Cl
OH OCH3
H 3C

(3) Cl (4) Cl
ANS:4
SOL:
OH O O  CH 3
OH  CH O  SO OCH

3 2 3
Cl Cl Cl
20. Match the multistep conversions in Column – I with appropriate sequence of
reagents given in Column – II.
Column I Column II

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 (A) NO 2 (P) (i) Ac2O
(ii) NO2+BF4-
O
(iii) NaOH/∆
CH3

(B) (Q) (i) Con.HNO3/Con.H2SO4

NO 2 (ii) Ac2O/anhyd.AlCl3

(C) (R) (i) CH3COCl/anhyd.AlCl3

(ii) Con.HNO3/Con.H2SO4

NO 2

(D) NH2 NH2 (S) (i) CH3CH2CH2Cl/anhyd.AlCl3

(ii) t-BuCl/anhyd.AlCl3
(iii) Con.HNO3/Con.H2SO4
NO 2

(T) (i) CH3CH2COCl/anhd.AlCl3

(ii) Con.HNO3/Con.H2SO4
(iii) NH2NH2/NaOH/glycol

ANS: A – R;B – S;C – T;D– P

SOL:

23. Which of the following heterocyclic compound/s might be aromatic?

(A) NH (B) BH

(C) (D) B H
O
ANS:BC
SOL:
76. Which of the following will have fastest rate of reaction with Br2 / FeBr3 ?

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 NO2 CH 3 OCH 3

1) 2) 3) 4)
ANS:4
SOL: OCH 3 group is +M.E group which activates the benzene ring.

84. The major product formed in this reaction is

  CH 3  3 CCH 2 Cl  AlCl
 3


CH 2 C  CH3 3 C  CH3  2 CH 2CH3

1) 2)
CH  CH3  CH  CH3  2 CH  CH3  CH2 CH2 CH3
3) 4)
ANS:2
SOL:
Paragraph for Questions Nos. 12 to 14
A hydrocarbon P (C11H8) on treatment with dilute H2SO4 in presence of HgSO4 forms
Q(C11H12O2). P on treatment with B2H6/H2O2 – NaOH gives R which is an isomer of Q. Q
gives yellow precipitate with NaOI while R doesn’t. R forms a grey precipitate on treatment
with ammoniacal silver nitrate solution. P on boiling with alkaline solution of KMnO4 forms
C8H6O4, which on heating with P4O10 yields S(C8H4O3). S on treatment with toluene in
presence of anhydrous AlCl3 yields T(C15H12O3) as the major product. T is reduced by Zn-
Hg/Con.HCl and product obtained gives the following compound on reaction with HF.

Me
O
12. Which of the following products are formed when Q is treated with aqueous NaOH?

Me
O
Me
Me
O
O Me O
I II III IV

(A) I & IV (B) I, II & III (C) II & III (D) I, II, III & IV
ANS:A
SOL:

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 CHO

CHO
HBO
CH

[P] CH [R]

+
KMnO4
H2O/H

O
O CH3 COOH

O
CH3
COOH

O [S] O

[Q]

-
OH
O

NH
O
NH

[T]
+ O
O

13. S on heating with hydrazine hydrochloride gives

(A) O (B) N
O
NH N
NH

O
(C) O (D) N
N N
N

O
ANS:A
SOL:
CHO

CHO
HBO
CH

[P] CH [R]

KMnO4
H2O/H+

O
O CH3 COOH

O
CH3
COOH

O [S] O

[Q]

-
OH
O

NH
O
NH

[T]
+ O
O

14. The structure of R is

(A) O Me (B) CHO

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Me CHO

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 (C) Me (D) Me

O O
O

Me CHO
ANS:B
SOL:
CHO

CHO
HBO
CH

[P] CH [R]

KMnO4
H2O/H+

O
O CH3 COOH

O
CH3
COOH

O [S] O

[Q]

-
OH
O

NH
O
NH

[T]
+ O
O

39. Match List-I with List-II and select the correct options given below:

List-I (Compound) List-II (Property)

(P) Dihydro furan (1) Non-planar structure

(Q) Borazine (2) Antiaromatic

(R)Cyclooctatetraene (3) Aromatic

(S) [12] Annulene (4) Five membered ring

Codes:

P Q R S

(A) 2 3 1 4

(B) 4 1 2 3

(C) 4 3 1 2

(D) 4 3 2 1

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ANS:C
SOL:
24. Which of the following is the correct order of reactivity towards nitration?

A) C6H6 > C6D6 > C6 T6 B) C6D6 > C6H6 > C6 T6

C) C6 T6 > C6D6 > C6H6 D) C6 T6 = C6D6 = C6H6

ANS:D
SOL:

29.

O O
Path I O 2N  
 O 2N
Anh. AlCl3  HCl
Cl

(P)

O O
Path II O 2N  
 O 2N
Anh. AlCl3  HCl
Cl
(P)

The correct statement among the following about the above two paths of synthesizing

the organic product P is:

A) Path I is better than Path II

B) Path II is better than Path I

C) Both the paths are equally good

D) Path I will give less yield of the product as compared to that obtained by part II

ANS:A
SOL:

7. The major product formed in the reaction is:

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 + HNO3 
conc.H 2 SO4


NO2

NO2
A) B) C) D)
NO2
NO2

ANS:B
SOL:
29. Major product obtained in the following reaction is
H2SO4
2

A) B) C) D)
ANS B

Conceptual

30. Which of the following compounds form ortho benzene dicarboxylic acid when
oxidized by hot. Aq. KMnO4

A) B) C) D)

ANS B
Conceptual
30. Among the following , aromatic compounds are

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 (A) (B) (C) (D)
ANS ABD

(14) Annulenes are aromatic B is more aromatic than A

34. In which of the following reaction t-butylbenzene is formed?
a) Benzene + iso-butyl chloride, AlCl3

b) Benzene +  CH3 2 C  CH 2  

BF3 . HF

c) Benzene + t-butyl alcohol 

H SO2
 4

d) Benzene +  CH3 2 C  CH 2  

AlCl3

ANS ABC
27. Benzene reacts with fuming sulphuric acid to give

a) Sodium benzene sulphonate b) benzene sulphonic acid

c) Sodium benzoate d) all the above

ANS B

SOL

SO3H

fuming H 2 SO 4

70. Which of the following compounds has most acidic hydrogen ?

O S

1) CH 2) CH
O S

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 R
O
N
CH
3) CH 4)
N
N
R
R
ANS:2
SOL:

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