(c) high pH (d) any pH

4. Which of the following has the lowest heat of combustion ?

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

5.

Br
12
The product obtained from the reaction is :

CH2Cl + NaCN
ethanol

(a) Br CH2CN (b) Br CH2Cl

(c) NC CH2CN
AROMATICCOMPOUNDS (d) Br CH2Cl

516 EAS QUESTIONS

CN
CO
7 . How many benzylic hydrogensZn—
areHg,
present in the hydrocarbon
1.SOCl 2 shown below ?
6. + 1. AlCl O HCl, heat
3
A B C.
2. H 3O + 2. AlCl 3
CO
3. H 3O +
The end product (C) is :

(a)
11.
O
Level
OH OH
(b)
1
- of rate of reaction with Br AlCl is :
Increasing order 2 3
O OH
517

(a) 3 (b) 4 (c) 5 (d) 6 (e) 8

8. O
The major O
product formed in the reaction O
is : O
||
O NH – C – CH3 O
CH3 conc. H 2SO 4
C — C6H 5 (i) + (ii)
HNO3 C (iii) (iv)
1.
(c) (a) iii < i A< ii < iv (b) iv(d)< ii < i < iii (c) ii < iv < iii < i (d) iv < ii < iii < i
C
12. Increasing
C—C B6H 5order of equilibrium constant for the formation of a hydrate is :
COOH
O O ONO2
O O
Identify the position
NO2 where electrophilic aromatic substitution (EAS) is most favourable.

1. (a) A H 3 C
O (b) B
(a)
(c) C (b) (c)A and C
(d) (d)
C H O NO O2 N
NO2 3 Cl 2 CH3
(i) (ii) NO 2
(iii) (iv)
9 . The major product formed in the reaction is :
2 . (a) i < ii < iii < iv (b) iv < ii < i < iii (c) ii < iv < iii < i (d) iv < ii < iii < i
O
1 3 . Rank the following reactions A, B and C in order of increasing rate,
Conc. HNO 3 / conc. H(c)
2SO 4 (d)
(a) Me
C – O (b) Me Me Me
(mononitration)
Correct order of rate of EAS (electrophilic aromatic substitution) is :
SO3H
(a) c > b > https://t.me/studyzee
a >d O (b) c > d > a > b SO3/ H SO2 4
SO / H SO2 4 O
(c) a > b > c > d 3
(A) (d) c (B)
>d >b >a
(a) C–O (b) O2 N C–O
2. O2 N
NO2 NO2
SO3H

O O
(c) CSO
–O 3/ H SO
24
(d) C–O NO2

3. (C)
NO2
SO3H
10. Increasing order of rate of reaction with HNO
3 2 4 H SO is :
(a) B > A > C (b) B > C > A (c) A > B> C (d) A > C > B
14. Rank in order https://t.me/studyzee
O of increasing rate Oof reaction towards
O EAS with bromine in the presence of
FeBr 3 . O O O O
O O
O O O

(A) (i) (B) (ii) (C) (iii)

(a) iii < i i < i (b) ii < iii < i (c) i < iii < ii (d) i < ii < iii
(a) B < A < C (b) B < C < A
4. (c) A < B < C (d) A < C < B

1 5 . 520
Cl
Cl
Identify the position where E.A.S. can take place.
(a) 1 https://t.me/studyzee
(b) 2 (c) 3 (d) 4
24. + HO ( A) ; Product (A) of the given reaction is :
Cl (4 mole) (major)

5. Cl
(2 mole)
519
2 0 . Arrange the following in increasing order of rate of Nitration:
Cl Cl
Me D NO2 Cl
O DCl Cl O Cl
D
(a) (b)
Cl O D D Cl O Cl
D
(a)
Cl
( b) https://t.me/studyzee
(c) (d)
Cl Cl
( e)
Cl < c < a < dO < e
(a) b Cl (b) d < e < aO = c < b
(c) d < a = c < e < b
(c) (d) a < c < b < e < d
(d)
O O
Me Me Me
6.
21.
H Cl H Cl H D Cl D Cl D
25. In which of the following compound electrophilic aromaticsubstitution take place in phenyl
ring present in left hand side ?
(a) O (b) O (c)
The rate of nitration will be:
(a) a > b > c C — O (b) a > c > b
(a) (c) a = b = c C — NH(d) c > a > b
(b)
2 2 . The major product of the reaction is
O

CH2 — O 1. CH 3COCl / AlCl 3 CH2 — C

(c) (d) Product .
2. H 2O

7. O CH3
; Reactant (A) is||C
H 2SO 4
26. +A :
(a) CHO
3–C (b)
| CO2H
O O O
(a) O (b) (c) (d)
| CO2H
O
27. Which of the following compounds is the slowest to react with nitrosonium ion ( NO + ) ?
(c) (d) CH3
O OMe
||C C
||
(a) O CH3 (b) (c) O CH(d)
3

2 3 . Arrange in their decreasing order of rate of electrophilic aromatic substitution :

 521
O O
|| ||
28. (CH 3 ) 2CH –C– Cl Clemmensen CH 3 –C– Cl NaCN Red P + HI
(Ibuprofen)
523
AlCl 3 reduction AlCl 3 H 2SO 4 H 3O ≈
32. Rank the following in order of decreasing rate of reaction with alkoxide ion (CH 3 CH 2 O ) in
Ibuprofen is :
a nucleophilic aromatic substitution
CH 3 reaction :
Br | Br Br Br
(a) CH 3 — CH 2 CH — CO 2 H
NO2 NO2
(b) CH 3 — CH — CH 2 CH — CO 2 H
| | 523
CH 3 CH 3 NO2 NO2
32. Rank the
CH3following
– CH CHin order of decreasing rate ofCOOH
reaction with alkoxide ion (CH 3 CH 2 O ) in
3
a nucleophilic aromatic substitution reaction :
NO2 NO2
Br 1 Br 2 Br 3 Br 4
(c)
(a) 3 > 4 > 1 >NO2 (b) 3 > 4 > 2(d)
> 1 (c)2 2 > 1 > 4 > 3
NO (d) 4 > 3 > 2 > 1
2
33. Identify the principal organic product of the following reaction.

8. O F NO2 NO2
523
CH2 C + NaSCH
AlCl NO2 product NO2
3 3
3229. . Rank the following in orderOof2 decreasing
Br rate of reaction with alkoxide
4 ion (CH 3 CH 2 O ) in
O
1 N
2 aromatic
3
CH 2 CH
a nucleophilic Csubstitution reaction :
(a) 3 > 4 > 1 > 2 (b) 3 > 4 > 2 > 1 (c) 2 > 1 > 4 > 3 (d) 4 > 3 > 2 > 1
Br Br Br Br
33. O F product of the following reaction.
Identify the principal organic SCH3
What is the major NO
product of above Friedel-Craft reaction
NO2 ?
2 F
(a) O O
(b)
CH3S CO2H Br+ NaSCH 3 product O2N Br
O2N Br NO2 NO2
(a) (b)
NO2 NO2
F CO2H
SCH
CH3S1 O F2 3 4 3 F
(a) 3 > 4 > 1 > 2 (b) 3 > 4 > 2 > 1 (c) O
(a) CO2H (b)2 > 1 > 4 > 3 (d) 4 > 3 > 2 > 1
3 3 . (c) Br (d)
9.
CH3Sthe principal organic
Identify O2N
product of the following reaction. Br
(c) O2N F Br (d) O2N SCH3
CH S CO2H
+ NaSCH 3 product
What 3combination
3 43.0 . Which position of Facidbe
will attacked most F
rapidly by the nitronium ion ( –NO 2 ) + when the
Br chloride or anhydride and arene would you choose to prepare
O2N
given compound ?
compound
(c) undergoes nitration with HNO (d) 3 H 2 SO 4 :
O2N Br
F A B C D O2N SCHSCH 3
3
O
34. Which
(a) (b) by the nitronium ion ( –NO 2 ) + when the
position will be attacked most rapidly
CH3S undergoes Br C — CH — CH2 — CO2HO N OCH3 Br
compound nitration 2with HNO 3 H 2 SO2 4 :
AO B C D
O
(a) CH
A 3S F (b) B (c) C F (d) D
OCH3
NH2
10. (c)
(a) A O2N Br
(b) B (c) OC
2N SCH(d)
3 D
(d)

NH2 position will be attacked most rapidly by the nitronium ion ( –NO 2 ) + when the
34. Which Conc.H SO Br H O
2 4 2 2
35. ( X)with HNO H SO
compound undergoes nitration ( Y):: Product (Y) of this reaction is :
excess
3 2 4
A B C D
Conc.H 2O
SO 4 Br 2 H 2O
35. NH2 ( X) NH
( Y): Product (Y) of this reaction is 2:
excess OCH3
NH2
(a) ABr
NH2
SOB 3H
(b)
https://t.me/studyzee
(c) C Br (d) D Br
(a)NH
Br 2 SO 3H Br (b) Br
524
(a) (b)
Conc.H
NH 2SO 4 Br 2 H 2O
35. 2 ( Y): Product (Y) ofNH
( X) this
2 reaction isSO
: H
524 Br excess
SO3H
3
Br Br
Br NH2 Br NH2 Br
NH2 NH2
(c) (d)
Br SO 3H Br
Br SOBr3H
Br Br Br
(a) Br (b) Br
(c) (d)
3 6 . All the hydrocarbons shown are very weak acids. One, however,SO H more acidic than the
is3far
others. WhichBr one is the strongest acid ? SO3H
Br Br

11.
36. All
(a) the hydrocarbons shown
(b) are very weak acids.
(c) One, however, is far(d)
more acidic than the
others. Which one is the strongest acid ?
https://t.me/studyzee
(a) O (b) https://t.me/studyzee
(c)
2. SOCl2
(d)
4. MeOH
1. AlCl3 3. NaN3 5. LiAlH4 6. NaH,
37. + O (A) (B) (C) (D)
O CF3
2. SOCl2 4. MeOH 7. 8.
O 1. AlCl3 (A) 3. NaN3 5. LiAlH4 6. NaH,
37. + O https://t.me/studyzee
(B) (C) Cl
CF3
(D)
Product (D) in above sequence is :
526 7. 8.
O CF3 CF3
Cl
O (D) in above sequence is :
Product
O CF3 O CF
43. Cl – C Cl (A) ; Unknown ( A)3 is :
AlCl3
(a) O NH — CH 3 (b) O

OH
(a) NH — CH 3 (b)
N — CH3
OH O
OH C= O ||
(a)
(c) (b) C = O (d) (c) NH CH(d)
3 Ph C Ph
N — CH3
OH 525
39. What is Cthe=correct
O order of oCF p ratio when E + attacks the following NH system ? CH3
(c) (d)
| 3
3 8 . PhF PhCl (excess) on salicylic PhBr PhI

12.
The action
Cl of bromine water Cl Cacid results in the Cl formation of :
A B D
(a) A < B < C < D (b) A CF = 3B = C = D (c)BrD < C < B <COOH A (d) D < B < A < C
3 8 . The Br
action of bromine water (excess)
H2SO on salicylic acid results in the formation of :
4 0 . How many productsCOOH are capable of beings
4 formed(1) NBS
from toluene in each ofRCO 3H
following reaction ?
4 4 . (a) + ( A) Br
Mono-nitration
(COOH
B)
OH
( C) . Product (C) is :
(2) alc. KOH
(b)
Br COOHCH3 O3 (A) O
OH N Br
H
SO 4 OH
(a) Br Br H 2 °) (b) Br OH
COOH
(a) O (b) ( 40 O
OH Br(c) (d)
HNO
(c) Br Br
OH 3 (d) Br COOH
Br
OH
H2 S
O Ph
Di-nitration
HNO3 (80°) 4 (B)
(c) Br
HOH (d) Br Ph
2SO 4 Br
(110°)
4 5 . The reaction
Br of toluene w ith chlorine in the presence
Br of light gives :
Tri-nitration
(C)
CH3 CH3 CH2Cl CH3
(a) ACl
= 3,B = 6,C = 8 Cl Cl (b) A = 3 , B = 6 , C = 6
(c) A = 3 , B = 6 , C = 10
(a) (b) (d) A = 3 , B =
(c) 4 , C = 6 (d)

13.
41. Nitration takes place at the which position of the given compound ?

Cl https://t.me/studyzee
CMe3
Cl
O D A NH2 –NH
46. + https://t.me/studyzee
AlCl3
( A)
2
( B), Product (B) in this reaction is :
ClC H2 O HO– ,
B
CHMe2

(a) A (b) B CH2 – OH

(a)
(c) C (b) (d) D (c) (d) OH
CH2 — CO H

14.
2
Ac2O HF
42. + ? , Indentify the product.
47. Suitable product of this reaction is :
CO2H
CH2 — CCl Ac 2 CH2 — CO H 2
(a) (b)
CO2H CO2Ac

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

O
(c) (d) O
O
O O
 SH CH2 – SH SH
(a) (b) (c) (d)
(a) (b) no reaction (c) (d)
(a) a (b) b (c) c (d) d
5 9 . The electrophilic aromatic substitution proceeds through a :
CH3 Cl Cl
(a) free radical (b) sigma complex (c) benzyne (d) carbene
NH
6 0 . Which2 of the following substitution of benzene is ortho-para in electrophilic substitution and
ortho-para inBrnucleophilic
2 substitution
(i) NaNO 2/HCl ?
49. (A) ( B) , Product (B) in this reaction is :
(a) – NO 2 H2 O (ii) H3PO 2 (b) – NO
530
(c) – SO 3 H (d) – SO 2 Me
AlCl 3
616 4. . Ph
TheNOnumber of possible
2 + Et Cl
Br ( A)isomers of ofdichloronitrobenzene
, Product ( A) the given reaction is Br
: is : Br
NO NO2
(a) 3 Br (b)Br 4 Br 2 (c) 6
Br Br (d) 8 531
7 1 . (a)
Two
(a) Phbenzyne
(b)
– NH – Et intermediates are likely
(b) no–reaction
(c)
(c) to be formed equally.
(d)
(d) with amide ion can
Reaction
6 2 . Which
occur inoftwo
thedifferent
following is not an
directions aromatic
with compound
each benzyne,
Et giving?three possible products. They are
14 Et
formedBrin a 1 : 2 : 1 ratio. Asterisk
Br (*) refers to C.
6 5 .l In nitration
* of benzene by mixed acid the rate of reaction will be :
(a)
(a) CCl NaNH (b) (b) C6 H 6 > C6 D(c) (d)
15.
6 H 6 = C 6 D 6 = C 6 T6 2 6 > C 6 T6
(c) C6 H 6 = CCl (A) Product (d) major;
C6 H 6product A Tis
< C6 D 6 <( C ) :
6 D 6 > CNH
6 T3
6 6 6
NH2 Na2S
50. (A), Product ( A) in this reaction is* :
6 3 . 2Consider the
H2SOfollowing
NH 2 5 (A)
sequence
Ph – CH 2CN of reactions. NH2
66.
* COOH
EtO –/ * (B) ; Product (B) is :
1. SOCl2 Zn-Hg
NO2 NO2 A B
(a) (b) (c)AlCl3
NH2.2 anhyd. (d) Conc. HCl
(a) Ph
N = C CN CH2C6 H(b)5 Ph N = C PhSH
NH2
Cl |
The end product
Ph ( B is:
) *S
7 2 . Which one of the following undergoes nucleophilic aromaticsubstitution at the fastest rate?
N = N OPh
(c) Ph Cl (d) Ph CH = CH Cl Ph NO2
(a) (b) SCl (c) (d) Cl CHO
6 7 . Which of the following ring compounds obeys Huckel's rule ?
(a)
532(a) C4H 4
1
(b) C4 H(b)
+1
(c) C4 H 42 (c) (d) C4 H 4 (d)
4 NO
(a) (b) (c) NO2 (d) 2 CH2C6 H
6 8 . NitrationSH
of which of the following reactant gives maximum % of meta product (using 5
7 8 . What
HNO is the product obtained by heating the following allylic ether of phenol ?
3 H 2 SO 4 ) ?

16.
OCH2CH = CHC H5 6
(a) Toluene
NO2 NOCl (b) Aniline CH3 OCH3
(c) Benzene 2 (d) Isopropyl benzene
Br
Br
7 3 . Ph
For the reaction
Ph ; ? O–H ; t hebest combination of reactants is :
NHOH
2 2AgBF OH C| 6 H 5
NO
69. ( x ) 2BF4 ; 4
compound (x) 2will be :
CH2CH = CHC H5 6 CHCH = CH
(a) C6 H 5NaNO
Ph
(a)
BrPh+2HNO
/ HCl 3 , H 2 SO 4
(b)
(b) C6 H 5 Br 2+ H 2 SO 4 , heat
51. (A) (B), Product (B) of this reaction is :
(c)BrC6 H 5 NO 2 + Br 2 , FeBr(mild
3 (d) C6 H 5 NO 2 + HBr
basic medium) ( Major)
Ph Ph Ph Ph
7 4 . The Ph action of AlCl Ph Ph
3 in Friedel Craft’s reaction is:
Ph
(a)CHto
(a) OCabsorb
H + 52 HCl (b) –2 (c) +1
(b) (d) HCl –1
to release
3 6
CH2CHPh = CH Ph Ph
C2 H 5
(c) toPh produce electrophile 2 Ph (d) toPhproduce
| PhnucleophilePh
(c) (d) HO
https://t.me/studyzee
KMnOCHCH = CH2
17.
7 5 . n-Butylbenzene
7 9 . When
O
(a) benzoic
you ingest acid
on oxidation with hot alkanine
aspirin,
(1) CO 2
(b) butanoic
it passes through youracid stomach,
(c) which
4 gives :
benzyl
hasalcohol
an acidic pH,(d) benzaldehyde
before
7760 . traveling
Which through
sequence theof basic environment
steps
(A) describes ofthe
yourbest
intestine. Provide
synthesis of the structure form as?i t
2-phenylpropene
exists in the intestine.
(2) H ≈
(a) Benzene
O + 2-chloropropene , AlCl 3 O ?
Which of the following is true statement about the reaction
(b) 1. Benzaldehyde (C6 H 5 CH = O) + CH 3 CH 2 MgBr , diethyl O etherO
O – Cisomer
(a) Ortho – CH+ 3 OH
is major if PhONa is used O – C – CH 3
2. Hisomer
(b) Para 3 O is major if PhOK 3. His2used
SO 4 , heat
CO2H CO2CH 3 CO2 C – OH
(c)
(c)Product
(a) formed is (b)
1. Bromobenzene further+used
Mg,for preparation
diethyl (c) of drug
ether 2. aspirin
Propanal
(d)(CH 3 CH CH2 = O)
(d) All of these+
3. H 3 O https://t.me/studyzee
4. H 2 SO 4 , heat
8 0 . Which of the following sets of reagents, used in the order shown, would be enable for the
(d) 1. Bromobenzene
preparation + from
of p-chlorophenol Mg, p-chloronitrobenzene
diethyl ether 2. ?Acetone [ (CH 3 ) C2 = O]
(a) 1. 3.
Fe,HHCl +; 2. NaOH ; 3. NaNO , H SO ; 4. H PO
3O 2 2 4 4. H32 SO2 4 , heat
(b) 1. Fe, HCl ; 2. NaOH ; 3. NaNO 2 , H 2 SO 4 ; 4. H 2 O, heat

18.
7 7 . (c)
What are
1. Fe, HClthe; products
2. NaOH of
(d) 1. NaOH, heat ; 2. HCl
; 3.theNaNO
following reaction ?
2 , H 2 SO 4 ; 4. ethanol

OCHundergoes
excess HBr
8 1 . Which one of the following compounds 2CH OH 2 bromination
heat of its aromatic ring
(electrophilic aromatic substitution) at the fastest rate ?
(a) Br OCH2CHhttps://t.me/studyzee
Br (b) Br + BrCH 2CH OH
(a) (b) 2 (c) (d) 2
NH
N NH
OH H O
(c) O OH + BrCH2CH Br2 (d) Br + BrCH2CH Br2
19.
8 2 . 534
CH 3 C Cl
||
( P)
Anhy. AlCl 3
( Q). Product (Q) in this reaction is :
8 8 . Which of the following molecules is expected to have O
the greatest resonance stabilization ?
534 O – Me OCOMe OMe
(a) (b) (c) C – Me (d)
8 8 . Which of the following molecules is expected to have the greatest resonance stabilization ?
8 9 . (a) (b) the major product(c) (d)
20.
In the reaction given below, formed is :
(a) (b) O (c) (d)

OH OH
8 9 . In the reaction given below, the major productBrformed
2(1 mole)
is :
N Product.
O Fe

https://t.me/studyzee
O O Br2(1 mole)
Br N Product.
Fe

(a) N (b) N
O O
Br
(a) N (b) Br N
O O
Br
https://t.me/studyzee N Br
(c) O N (d) O

(c) BrN (d) N Br

9 0 . p-aminophenol reacts with one equivalent of acetyl chloride in the presence of pyridine to
give mainly :
Br O
OCOCH3reacts with oneOH
9 0 . p-aminophenol equivalent of acetyl chlorideOH in the presence of OHpyridine to
21. give mainly :
(a) OCOCH3 (b) OH
O
C – CH 3
(c)
OH 539
(d) OH
CH2CH3 C – CH 3
O C – CH3
CH CH NH2
(a) NH2 2 3 (b)
CH3 — C — Cl NH 2 (A) (c)
NH2 — NH , NaOH 2 O (B) (d) NHCOCH3
112. AlCl3 triethylene glycol. heatC – (CH
( 80%)be used 3
73%)
9 1 . Which of the following reactions can to prepare
NH acetophenone ?
NH NH3 2
1. AlCl 2 O NHCOCH3 heat
(a) C6 H 62 + CH 3 COCl (b (C6 H 5 COO) 2 Ca + (CH 3 COO) 2 Ca
CH CH 2. H 2O
9 1 . Which2 of 3the following reactions
1. CH 3 MgI1. AlCl
can be used to prepare acetophenone ?
Product ( B is
)
(c) CC6HH 6+CN : of theseCa + (CH COO) Ca heat
(a) 6 6 CH 3 COCl2. H O+
3
(b(d)
(C6All
H 5 COO) 2 3 2
3 2. H 2O
1. CH 3 MgI
9 2 . (c)
Consider the following
C6 H 6 CN sequence of reactions.
(d) All of these
2. H 3O+
H3 P
O 4 1.O 2, heat
9 2 . Consider
(a) theCfollowing
6 H + CHsequence
6 (b) 3 CH = CH
of 2reactions.
heat
(c)
A +
2. H 3O (d)
, heat
B+ C
The products (B) and (C) are : H3 P O 4 1. O 2, heat
C6O H +6 CH 3 CH = CH 2 A B+ C
(a) benzaldehyde and acetaldehyde heat 2. H 3O + , heat
(b) benzoic acid and acetic acid
22. The
(c)
540
9 3 . (a)
products
phenol
An benzaldehyde
||
and(B)
1 1 3 . C 6 H 5 (CH 2 ) 5 C Cl
organic compound
and (C)
CS2
are
propionaldehyde
AlCl 3 :
( A)
and acetaldehyde
C12H14O
having
KMnO 4 , D
H 3Or
the molecular
(d) phenol
( B) ; Compound (B)
(b) benzoic
formula C8acid
andis :acetone
H01O andonacetic
beingacidheated with I 2 and
dilute
(c) NaOH
phenol CO
andgives 2Ha yellow precipitate. The(d)
propionaldehyde expected
CO2Hcompound
phenol and acetoneis :
HNO 3 Base SOCl (1) Et 2NH
19135.. An(a)organic compound having the
(1) molecular
(b) formula
(2) C82 H0(3) O on being
1 heated
(4) with I 2 and
(a) CNaOH n PrCl
dilute
HO 6 H 5 CH 2 CH a
gives 2 OH
yellow precipitate. (b) CHcompound
The expected 3 CH
: H22 OH
is(2) Pd
C — (CH 2) 4— CO2H
product
(a) C6 H(4) in the above reaction is : (b) CH3
5 CH 2 CH 2 OH CH2OH
O O O
O
NO2 C — N — Et NH2 C — N — Et
CO2H C
(a)
(c) Et (d) (b) O
C Et
OCO2H O
O O
R O
NH2 R R NO2

HNO3 C — NO
NH2— Et C — NEt 2
1 1 4 . (c) H2 SO 4
https://t.me/studyzee
+ (d)
O
Cl
(ortho)
https://t.me/studyzee
NO
O
2
In the above reaction o/p ratio will be highest when :
Br
(a) R = CH 3 (b) R = CH 2 CH 3
 S — S
Cl 2
124. ( A), Product (A) of this reaction is :
HNO
NO2 NO 2 3 Zn(Hg)
125. (A) (B), Product
SH (B) of this reaction
NO2 is :
H 2SO 4 HCl
SH S — Cl
CH2 — Me CH2 — Me O C — Me CH2 — Me
(a) (b) (c) (d)

23.(a) NO2
(b)
NO2
NO(c)
NO2
(d)
NO2
O 2

NO2 NH2
C — Me
Me NO2
HNO 3 Zn(Hg)
125. (A) (B), Product (B) of this reaction is :
H 2SO 4 HCl
3 AlCl H 3O +
126. +HN = CH
CH2 — Me
Cl CH — ( A)
Me O
( B), Product (B) of this reaction is :
C — Me
2 CH2 — Me
NO2
(a) Me (b)
CH3 (c) (d)
NO2 NH2

(a)Me (b) NO
(c)2 No-reaction (d)

24.
126. +HN = CH
CHO
Cl
AlCl 3
( A)CHO
H 3O +
( B), Product (B) of this reaction is :
O C — Me

CH2CO H 2
Me CH3

EtOH (i) NaH (i) NaOH (i) SOCl 2

127. (a) (b) H+
; Product
(ii) H+
(ii) MeI (c) No-reaction (ii)(d)
AlCl 3
CHO O C — Me
End product of the aboveCHO
reaction is : 543
CH2CO O
H2

Me
EtOH (i) NaH (i) NaOH (i) SOCl 2
127. ; Product
H+
(ii) MeI (ii) H+ (ii) AlCl 3
(a) (b)
End product of the above reaction is :
O O O

(c) (d)

≈ –

25. https://t.me/studyzee
CH 3 Cl (2 mole) Ph N 2 Cl
128. Ph NH 2 (A) (B) (major)
Butter yellow 545
Product of the above reaction is :
NO2
Me N Me Me — N — Me
Br 2 (2 mole)
N == (NA)—(major)
Ph
https://t.me/studyzee
134. ; Product (A) will be :
Fe
(a) (b)
NO2 NO2 NO2 N == N — Ph NO2
Me
Me — N — Me Br Br Br
(a) (b) Me — N — N == N — Ph(d)
(c)
Br Br Br
(c) (d)
Br Br
N == N — Ph

26.129. p-Toluedine reacts with benzene diazonium chloride to form compound, which on boiling
with aq. H 2SO 4 give ......... products :
(a) 3
(i) HNO 3
(b) KMnO 4 SOCl 2
547
135. OH ( A2) (c)
( B) 4 (d) 5 (C) of this reaction is :
( C); Product
(ii) H 2SO 4
NO2 (Di- nitro O O
product)
H2 O OC(i)—NaNO
Cl + HCl 547
1 4103.0 . COCl
aq NH 3 (A) Br 2
2 (B)) ; Product (B) of this reaction is :
(A) ( B) (C
OH Pd H 2O (ii) H 3 PO(Paracetamol)
NO22
NO2
NO2 O O NO2
(a) Cl (b) (c) (d)
NO2 H
Product 2
NO2 (C) of the(A) O is :
above reaction
140. ( B) ; Product (B) of this reaction is NO
: 2
NO2Pd
O (Paracetamol)
NONO2 2 NO 2 NO2 NO2
Br O Br
Cl 2 O — C — CH 3
NO
OH OH NH2
(a) (b) (c) (d)
O
Br Br Br Br CBr— CH3
Fe
(a) OBr— C3 — CH 3 3 (b)
CH — NH—CH O reaction is : (d)
136. ( A)OH
HCl
(c)(B)
( B) ; Product OH of this NH 2
C — CH3
NO2 NH
(a)
2
(b) HN (c) NH2 (d) OH
CH3 CH3 CH3 CH3
N O N
NH2 O
27.
1 4 1 . (a) + O
HN
AlCl 3
Ohttps://t.me/studyzee
( A)
(b)
NH2
Zn(Hg)
( B)
H 3 PO 4
OH

( C) ;
O 2.2 equivalents HCl NH2
+ NH2 O
O AlCl 3 Zn(Hg) H 3 PO 4
141. (succinic 2.2 equivalents ( A) ( B) ( C) ;
HCl
anhydride)
CH
3 (C) of CHO3
Product the above reaction is :
N (succinic
anhydride)
NH O OH
2
Product (C) of the above reaction is :
(c) (d) None of these
548 O OH
O OH
(a) of the following 2-halo
1 4 3 . Which (b)nitrobenzene is most reactive
(c) (d) aromatic
towards nucleophilic
O OH
substitution ?
(a) F (b) Cl (c) Br (d) I
O
NO2 NO2 NO2 NO2

28. (b) O C
AlCl 3
1 4 2 . (a) + (c) Product ; (d)
O 82% yield
AlCl
142. + C H 3 Product ;
1 4 4 . Choose the best method to prepare
O given compound :
82% yield
CH3H
Product of the above Friedel-Craft reaction is :
CH3 CHreaction
Product of the above Friedel-Craft 3 is : https://t.me/studyzee O
O
C
CO2H C
(a) CO2H
(b)
(a) NO2 (b)
CO2H
(1) HNO
CO3+ HH
2SO 4 (1) Me3CCl AlCl 3
(a) 2 (b)
(c) (2) Me3CCl AlCl 3 (d) (2) HNO 3 H 2SO 4
(c) (d)
CH 3
|
(1) CH 3 —CH — CH 2 —Cl / AlCl 3 (1) HNO 3 H 2SO 4
(c) (d)
(2) HNO 3 H 2SO 4 (2) CH 3 CH CH 2 Cl AlCl 3
|
CH 3

29.
CH3
548
143. Which of the
HNOfollowing
3 2-halo nitrobenzene
H2 is most
KMnO 4 reactive
EtOHtowards nucleophilic aromatic
145. ( A) ( B) ( C) ( D)
substitution ? 4 (Para isomer) Pd,C
H 2SO H+ Benzocaine
F has been used as aClcomponent of appetite
Benzocaine I sunburn
Br suppressants, burn and
remedies. Benzocaine is :
NO2 NO2
https://t.me/studyzee
https://t.me/studyzee
O NO2 NO2
(a) (b) (c) (d)
CO2Et CO2Et C NH OEt

30.
144. Choose the best method to prepare given compound : C
(a) (b) CH3 (c) (d)
O
NH2 CH3 CH3
NH2 NH2
O — CH 3
HBr
146. ( A) ; Product (A) of this reaction is :
OH 86%
Br NO2OCH OH OCH — Br
 3 2 4 3 3
(a) (b)
(2) Me3CCl AlCl 3 (2) HNO 3 H 2SO 4
OCH3
HI(excess)
CH 3
147. |
Product.
OCH3 (1) CH 3 —CH— CH 2 —Cl / AlCl 3 (1) HNO 3 H 2SO 4
(c) (d)
Predict major product(2)ofHNO
the3 Habove (2) CH 3 CH CH 2 Cl AlCl 3
2SO 4 reaction is : |
CH 3 OH
OH I CH3
CH3
OH I O—I
(a) HNO 3 (b) H2 (c)4
KMnO EtOH (d)
145. OH ( A) I( B) ( C) ( D) OH
H 2SO 4 Pd,C H+
(Para isomer) Benzocaine
OH
Benzocaine has been used as a component of appetite suppressants, burn and sunburn
remedies. Benzocaine is :
O
HNO 2
148. (A) (Major) ; Product (A) is :
CO2HNO
Et 3 CO2Et C NH OEt
C OH
OH OH
(a) (b) (c) (d)
NO2 O
NH2
550
(a) (b)
NH2
(c) (d)
NH2
O — CH 3 NO2
31.
151.
146.
What is the product of theHBrfollowing reaction ?
NO
OH
( A) ; Product (A) of this reaction is :
86% CH3
1 4 9 . Arrange in their
Br decreasing order of OCH rate in SNAr. OH
H2SO 4 OCH2 — Br
3
OCH3 + C == CH2
(a)Cl Cl (b) Cl (c) Cl Cl(d)
OH Br OH CH
NO2 NO2 NO2
CH3 OCH3

(a) NO2
CHCH OCH3 (b) (CH3) 2CH
2
NO2 NO2 NO2
(i) (ii) (iii) (iv) (v)
OCH3
(a) i > ii > iv >CHiii3 > v (b) ii > i > iii > v > iv
|
(c) v > iii > i > ii > iv (d) v > iii > ii > i > iv
(c) CHCH (d) (CH ) 2CH OCH
32.
1 5 0 . Which one of the following compounds undergoes 3bromination
2 of its aromatic ring 3
https://t.me/studyzee
(electrophilic aromatic substitution) at the fastest rate ?
152. Which sequence represents the best synthesis of 4-isopropylbenzonitri551
le ?
(a) (b)
N
(CH
1. Air, V 2 53) 2
O , CH C∫∫ N
154. A, Product A is :
2. NH 3 ,
3. KOBr, H
4-Isopropylbenzonitrile
CO COOH
(c) 1 . Benzene +NH
(a) (d)
(a) NH(CH 3 ) 2 CHCl, AlCl 3 ;(b) 2 . Br 2 ,FeBr 3 ;
NH
3. KCN
(b) 1 . Benzene
CO + (CH 3 ) 2 CHCl, AlCl 3 ; 2 . HNO
NH2 3 ,H 2 SO 4
; 3. Fe, HCl,;
4 . NaOH 5 . NaNO 2O, HCl, H 2 O
O
(c) 1 . Benzene +(CH 3 ) 2 CHCl, AlCl 3 ; 2 . HNO 3 , H 2 SO 4 ; 3 . Fe, HCl ;
4 . NaNO COOH HCl 5 . KCN C
2
(c)
(d) 1 . Benzene + HNO 3 ,H 2 SO 4 ; (d) 2 . (CH 3 ) 2 CHCl, AlCl 3 ; 3 . Fe, HCl;
CONH
4 . NaNO 2 ,HCl,H
2 2 O; 5 . CuCN NH

33.
1 5 5 . WhatCHis3correct order of rate of nitration of the following compounds ?
+ 551
C 6 H 5 CH 3 Br
C6H 6 C 6 D 6 C 6 T6 C 6 H 5 Br 3 C6H 5 N R 3 C 6 H 5 NMe 2
A B 1. Mg Ether
C D E F G
153. +
1. Air, V2O 5A,
, Product A is :
1 5 4 . (a) G > A > B >2.CH>3OD > E > F A, Product
(b) A
G is
> :B > C > D >
(c) G > A > B =3.CKMnO
= D 4> OH
2. NH 3 ,
E3.>KOBr,
F
https://t.me/studyzee
(d) G > A > B > C =
A> F
D > E> F
4. H +
CO COOH
1 5 6 . (a)
COOH + COCl| NH
AlCl 3
[ X]
Na— Hg, HCl OH
(b) [ Y] ; Product Y is :
excess
OHCOCl
CO NH 2
CH3
(a) (b) O
(a) (b) C
COOHCOOH
(c) (d)
CONH2 NH
(c) (d)
34.
1 5 5 . (c)
What is correct order of rate of nitration of the
(d)following compounds ?

C6 H 5 CH 3 C6 H 6 C6 D 6 C6 T6 C6 H 5 Br 3 C6 H 5 N R 3 C6 H 5 NMe 2
+

157. Compound
A 8 is
A (CB7 H O) C
insoluble
D
in water,
E
dilute HClF & aqueous NaHCO
G 3 , but it dissolves
in dilute NaOH. When A is treated with Br 2 water it isconverted into a compound C7 H 5 OBr 3
(a) G >The
rapidly. A >structure
B > C > ofDA> isE: > F (b) G > B > C > D > A > F
(c) GOCH
> A 3> B = C = D > EOH > F (d) G OH
> A > B > C = D > EOH > F

COCl CH3
AlCl 3 Na— Hg, HCl
156. + | [ X] [ Y] ; Product Y is :
(a) (b) (c)
excess (d)
COCl
CH3
CH3

35.552
(a) (b)
552
https://t.me/studyzee
158. Give the product of the following reaction sequence :
158. Give the product of the following
1. HNO 3 H SOreaction
24 sequence :
2. H 2 dPC
(c) 1. HNO Product
(d)
3. NaNO 3 H SO24
2 HCl
2. H 2 dPC
4. CuCN
5. MeMgBr Product
157. Compound A (C 7 H 6. H 33.
O+NaNO
8 is insoluble
O) HCl dilute HCl
in2water, & aqueous NaHCO 3 , but it dissolves
4. CuCN
in dilute NaOH. When A is treated with Br water it isconverted into a compound C7 H 5 OBr 3
O 5. MeMgBr 2 CO2H
rapidly.CO 2H structure of A is :6. H O+
The OH
3
OCH3 OH OH OH
CO2H O CO2H OH
(a) (b) https://t.me/studyzee
CH3 (c) (d)
(a) (b) (c) (d)

36.
1 5 9 . Give the product of the following reaction sequence:
(a) (b) (c) CH3 (d)
1. HNO 3 H SO24
2. Br 2 FeBr
Product
3
CH3
159. Give the product of the following
3. H 2 Pd C reaction sequence:
4. Cl 2 FeBr 3
5. NaNO 2 HCl
1. HNO 3 H SO24
6. KI 2. Br FeBr
2 3
Cl Product I Br
3. H 2I Pd C
4. Cl 2 FeBr 3
Br Br 5. NaNO 2 HCl
Cl Cl Cl
6. KI
(a) (b) (c) (d)
I Cl I Br
I I Br
Br Cl
160. Br formed in the
Which represents an intermediate Clreaction of toluene and chlorine at elevated Cl
temperature in sunlight ?
(a) H (b) H
(c) (d)
(a) I CH3 (b) Br CH3 I
Cl https://t.me/studyzee
Cl
37.
160. Which represents an intermediate formed in the reaction of toluene and chlorine at elevated
temperature in sunlight ?
(c) H CH2 (d) H CH2
(a) CH3 (b) CH3
1 6 1 . The decreasing order of reactivity of m-nitrobromobenzeneCl(I), 2, 4, 6- trinitrobromo-benzene
Cl
(II), p-nitrobromobenzene (III), and 2,4-dinitrobromobenzene (IV), towards OH ions is :
(a) I > II > III > IV (b) II > IV > III > I
(c) CH (d) CH2
(c) IV > II > III > I2 (d) II > IV > I > III
162. Which one of the following compounds is most reactive for ArS 2 reaction ?
161. The decreasing order of reactivity of m-nitrobromobenzeneN (I), 2, 4, 6- trinitrobromo-benzene
Cl Cl Cl Cl
(II), p-nitrobromobenzene (III), and 2,4-dinitrobromobenzene (IV), towards OH ions is :
(a) I > II > III > IV (b) II >NO
IV2 > III > I NO2
(a) (b) (c) (d)
(c) IV > II > III > I NO2 (d) II > IV > I > III
162. Which one of the following compounds is mostNO
reactive for ArSN 2 reaction ?
 OH OH OH
OH
Br Br Br Br SO3H Br Br
(a) (b) (c) (d)
Br
SO3H Br
Br
169. Consider the following sequence of reactions : 557 557
COOH
(a)
(a)I >I >II II
> > III III
> IV> IV(b) (b)
IV >IVIII>> III
II >
> I (c) III(c) > IIII> >IV I>>II IVZn
(d) IIII > (d)
III >II I>> III
IV > 557
SOClII2 > I 1. AlCl 3
>— Hg I > IV
117777. . Which ofof
thethefollowing is the major product A
from sulfonation B of conc.
-tetralone ? C
Which following isCH
the
Cmajor
H product from
2. H Osulfonation
+ of -tetralone
HCl, heat ?
(a) I > II > III > IV (b) 2IV O>6 5III > II > I (c)3 III > I > IV > II (d) II > III > I > IV
O
The endofproduct
1 7 7 . Which (C) is : is the major product from sulfonation of -tetralone ?
the following
O OH2 SO 4 H2 SO 4
heat
heat
(a) O H2(b)
SO O
SO3H O 4 O
SO3H O heat O
C6 H 5 HO3S C6 H 5
HO3S
(a) SO3H OO (b) O
(a) (b) HO S
3
(c) O (d) O
(a) (b)
O O
(c) (d)
O O 559
38.
185.
(c)HO3S
Two aromatic compounds P and Q give productSO
(c) HO3S
R.3H
(d)
(d)

178. Which of the following procedures would be best for the preparation of phenyl benzyl ether ?
SO3H
C6 HOCH
HO
5 2C6 H
S 5
178. Which of the following
3 Reagent(s) procedures would be best for the preparation of phenyl benzyl ether ?
P C HQCl + C H CH O ( ) Na( + )
(a) (b) C6 H 5 O ( )SO Na3( +H) + C6 H 5 CH 2 Cl
6 5 6 5 2
C6 HOCH 5 2C6 H 5
1 7 8 . (c)
Which
2C6 Hof5 Cl
the following
+ Na 2O
procedures would be
(d) best
2C 6 H for
5
the
MgBr preparation
+ CH 2 O of phenyl benzyl ether ?
(a) C6 H 5 Cl + C6 H 5 CH 2 O ( ) Na( + ) (b) C6 H 5 O ( ) Na( + ) + C6 H 5 CH 2 Cl
39. Reactant
C
1 7 9 . Which 6 HOCH
of5theP,2following
QC6and
(c) 2C6 H 5 Cl + Na 2 O
(a) C6 H 5CH
H reagent
5 proceduresusedwould
Cl 3+ C6 H 5 CH 2 O ( ) Na(C
P
in above
Q+H) – ∫C
2
reaction
be best
∫ CH –CH
are : the following reaction ?
for achieving
(d) 2C 6H 5 MgBr
(b)3 C36 H 5 O ( ) Na
+( +CH
) 2O
Reagent + C6 H 5 CH 2 Cl
1 7 9 . Which of the following
(c) 2C H Cl
?
Na O
https://t.me/studyzee
procedures would be best for achieving the following reaction ?
CH (d) 2C H MgBr
Br(a)
+
6 5 — C —2Cl Br 3 6 5 AlCl 3 2 O
+ CH
CH3 CH2– ∫C∫ CH –CH3 3
1 7 9 . Which of the following ? procedures would be best for achieving the following reaction ?
(a) (i) KOH and heat O (ii) CH 3 C ∫ ∫ C — Br
Br (i) KMnO CH
(b) 3 heat (ii)BrCH 3 C ∫ ∫ C( C)H 2–( + )∫C∫ CHexcess –CHH 3 2O3
4 and Cl Na (iii)
CH3
(b) — C — ?H ( ) AlCl 3
(c)
(a)(i)(i)NBS
KOH in CCl and heat
and4 heat (ii) (ii)
CHCH 3 C3 C
∫ ∫ ∫C∫ C— Na( + )
Br
Br Br ( ) ( +)
(b)(i)(i)Mg
(d) KMnO
in ether 4 Oand heat
(ii) CH 3(ii)
C ∫ ∫CHCBr3 C ∫ ∫ C
(iii) Na
excess (iii)
H 3 P
Oexcess 4 H 2O
(a) (i)
1 8 0 . Which KOH
of NBS and heat
the following (ii) CH 3would
procedures C ∫ ∫ C —best Br ( ) achieving( +)
(c) (i) in CCl 4 and heat (ii) CH 3be C ∫ ∫ ( C)for Na
( + )
the following reaction ?
(b) (i) KMnO 4 and heatO (ii) N CH 3 CCO ∫ ∫ CH
C
H 3 Na (iii) excess H 2 O
(d) (i) MgCH in3 ether (ii) 2CH 3 C ∫ ∫ CBr 2 (iii) excess H 3 P O 4
(c) (i) NBS in CCl?4 and heat (ii) CH 3 C ∫ ∫ C( ) Na( + )
40.
(c)
1 8 0 . ClWhich of the following procedures C == OBrwould be best for achieving AlCl
the3 following reaction ?
558(d) (i) Mg in ether (ii) CH 3C ∫ ∫ CBr Cl
(iii) excess H 3 P O 4
CH3 O2 N CO2H
(a) (i) Brof FeBr
2 +the (ii) KMnO and heatbe (iii) HNO and H 2 SO 4the following reaction ?
1 81 1
80. . Phenol
Which reacts following
3
with procedures
?acetone Clin 4thewould presence best offorconc.
3 achieving
sulphuric acid to form a C15 16 HO 2
(b) (i) KMnO 4 and heat (ii) Br 2 + FeBr (iii) HNO 3 and H 2 SO 4
OCl N Ocompounds
3
product.
Cl WhichCH of the following CO H is this product ?
Br
(c) (i) NBS in CCl34 and heat (ii) KMnO
2 2
4 and heat (iii) HNO 3 and H 2 SO 4
(d) O–Cin H 5 and ?heat (ii) Cl ZnCl 2
(d) Br 26 +CCl
(a)(i)(i)NBS FeBr
4 3 — C2 and
(ii)NaNO
KMnO heat CH
4 and heat (iii)3HNO 3 and H 2 SO 4
Cl
(a) Cl Br (b) HO OH
(b) (i)
O–C KMnO 4 and heat (ii) Br 2 + FeBr 3 (iii) HNO 3 and H 2 SO 4
6H 5
186. (a)
(c)
Which Br
(i) of
NBS2 +in
the FeBr
CCl 34 and
following H(ii)
C 6heat KMnO
(ii) KMnO
compounds 4 and
4 and
has aheat
heat(iii)
single(iii)
set HNO
HNO
of and
andHH22SO
structurally
33 SO44
equivalent hydrogen
6
atoms
(b)
(d) (i) ?KMnO
NBS in4CCl and heatheat
4 and (ii)(ii)
Br NaNO
2 + FeBr
2 and
3 heat(iii) HNO 3 and H 2 SO 4
O
(c) (i) NBS in CCl 4 and heat (ii) KMnO 4 and heat (iii) HNO 3 andOH 2 SO 4
(c) C6 H 5
(d) (i) NBS in CClH4 — C ∫heat
and ∫ C— (ii)CH 2 —2
NaNO CH 2 —
and C(d)
heat ∫∫ C— H
C6 H 5
41. I II O III IV V

(a) I and II O
(b) I and IV
(d) I, II and III (c) I and V
182. Heating benzene in ahttps://t.me/studyzee
large excess of 80% D 2 S
O in4D 2 O results in what product ?
187. Which of the following compounds would not be considered aromatic in its behaviour?
(a) C6 H 5 SO 3 D (b) C6 H 5 OD (c) C6 H 5 D (d) C6 D 6

42. A(a)
183. (b) in benzene is stirred
solution of cyclohexene (c) (d)
at 0°C while concentrated sulphuric acid is
added. NAfter washing away https://t.me/studyzee
the acid and removing N the excess benzene, what product is
1 8 8 . isolated?
A C 8 H 10 hydrocarbon si nitrated by HNO 3 and sulphuric acid. Two, and only tw o,
C H 9 NO 2 isomers are obtained. Which of the following fits this evidence ?
(a)8 cyclohexylbenzene
(a) ethyl benzene
https://t.me/studyzee
(b) ortho-xylene
(b) 1-cyclohexylcyclohexene
(c) meta-xylene
563
563
(d) para-xylene
220033 .. (c)
Thetrans-1,2-diphenylcyclohexane
The compound
compound formed
formed on heating
on heating chlorobenzene
chlorobenzene (d)
with1,1-diphenylcyclohexane
with chloral ni chhe
tloral ni he
presence t of presence of

43.Indentify
189.
184.
Which of the
concentrated
concentrated
(a)
(a)Freon
(a) Freon
—N ==
the benzylic halide T.
following
sulphuric
sulphuric
the reagentsS and
is benzene
acid,acid,
(b) DDT
O
: is :
(b)(b)
DDT— OCH 3(c) Gammexene
ring substituents is deactivating but ortho-para directing ?
in thescheme below in which R isconverted to the nitriteV via
(d) Hexachloroethane
(c) Gammexene
(c) — COCH 3 (d) Hexachloroethane
(d) — NO 2
204. Predict the product of the following reaction.
204. Predict the product of the following reaction.
O

1.
CHO2 — Br CH2 —CN
/AlCl3
1. Cl
(S) /AlCl3 ( )
(R) 2. Zn(Hg), HCl Cl
3. Br2, FeBr 3
2. Zn(Hg), HCl
O O 3. Br2, FeBr 3
O O
R, S and O
respectively are : AcO
2O
(a) (b)
R S
Br Ac2O
(a) Br https://t.me/studyzee
(b)
O
H — C— Br
(a) Br
Cl (AlCl 3 ) HCN
(c) (d) O
Br O Br
205. Predict the major product of the following reaction sequence.
CH2Br
44.(b) (c)
Br Cl 2 AlCl 3
A
1. Fe HCl
,
Cl —C —
B C
Br2 FeBr
(d)
3
D
NaOH
Br(AlCl 3 )
E
HCN
205. Predict the major product
2. NaOHof the following reaction sequence.
O CH Br
H 2 SO , NaNO
4 2 H3 P
O 2
H22 O
NO2 F H2 O
G
Cl 2 AlCl 3 1. Fe HCl
, Br2 FeBr 3 NaOH
A 2. NaOH Br
B C Br
D E
Cl
Cl Cl —C Cl—
(c)
(a) (b) (c) (d)( AlCl )
H 2 SO ,3NaNO
KCN
H3 P
O
4 2 2
NO2 F G
H2 O Br H2 O
Br Cl O CH2Br
206. Cl of the following reactionBr:
Give the major product ClO Br OCl
— C —(b)
Cl O CH Br
(d)
(a)
564 (c) 2 (AlCl 3 ) (d) KCN
NHPh Br
Br Cl
NHCOPh CH 3Cl , AlCl 3
NHCOPh
O
206. Give
(c) the major product
O of the following reaction : (d) O O
O

45. (a)
H3 C
CH3
O
NHPh
(b)
NHPh
NHPh
CH3
CH 3Cl , AlCl 3
H3 C

CH3
Br 2 O Sn HCl NaNO 2 + HCl H 3 PO 2 KMnO 4
207. ( A) ( B) (O
C) ( D) ( E)
Fe HOs
NHPh NHPh
(a) (b)
NO2
H3 C ( E is
Product ) :
CO2H https://t.me/studyzee
CO2H CH3 CO2H CO2H

https://t.me/studyzee Br
(a) (b) (c) (d)
Br

Br CO2H

46. F
NO2
O

208.
NH2–NH https://t.me/studyzee
A 2
B ; Products;
H+ ,

NO2
Incorrect statements regarding above reaction is
(a) Product A is 2, 4-DNP
 1. Each of the six compounds shown at the bottom of the page has two aromatic (benzene)
rings. In each case the two rings are different and are labeled A & B. I f an electrophi l ic
substitution, such as nitration or bromination, is carried out on each compound,
then identify which ring (A or B) will be preferentially attacked, and indicate the orientation
of the substitution (ortho/para, meta or all sites).
Compoun d Reactivity Substitution Compoun d Reactivity Substitution
A ortho/para A ortho/para
1. B meta 2. B meta
all sites all sites
A ortho/para A ortho/para
3. B meta 4. B meta
all sites all sites
A ortho/para A ortho/para
5. B meta 6. B meta
all sites all sites

Compoun d Compoun d

CH3
O
B | 581 B
F. The1 .cumulative effect of their fluorine activate the rings N
2 . of penta and hexa fluorobenzene
S
toward nucleophilic Aaromatics ubstitution. W hat iscompound X in the following synthesis?
OA

||
||
F O
F F
HOCH 2CH 2OH K 2CO 3 CH3
( A) ( X) (C8 H 4 F4 O 2 ) O
NaOH,
F F O N
B
3. F 4. A B
F O F
A
F O – CH = CH 2 F O – CH2 – CHON

||
O
(a) (b) CH3
F OH F H
CH3 O CH3
F O F
| B || CH3
F F
5. N 6.
F F O A
AO B
(c) O (d) CH3
582 F O F O

47. F F

582
G. Which is the best route for the synthesis of CH3O NO2 Strating from benzen of ?
Subjective Problems
NO2

Subjective Problems
(a)
Br 2
FeBr 3
HNO 3
H 2SO 4
HNO 3
H 2SO 4
NaOCH 3
CH 3OH
1.
HNO 3 HNO 3 Br 2 NaOCH 3

1.
(b)
H 2SO 4 H 2SO 4 FeBr 3 https://t.me/studyzee
CH OH OH 3

OH HNO 3 Br 2 HNO 3 NaOCH 3

(c) OH (mild - basic
H 2SO 4 FeBr 3 H 2SO 4 CH 3OH
. condition)
OH HNOdil HNO3 Br 2A + BNaOCH 3
(1) Sn|HCl
C D
(d) 3 (2) NaNO 2HNO
/HCl3 (mild - basic
H 2SO 4 More
FeBr 3
Less
CH 3OH H 2SO 4
condition)
dil.HNO3 volatile volatile (1) Sn|HCl

48. A + B C D
(2) NaNO 2/HCl
18. Identify bond
Double product (A)More
and write
equivalent LessDits
of is :structure.
volatile volatile
2. How many isomers 'x' of C 8 H 10 when reacts with hot alkaline KMnO 4 give only aromatic
Ph
dicarboxylic
Double bondacid
| ? How many
equivalent of D isisomers
: 'y' of C 4 H 8 when reacts with hot alkaline KMnO 4 give
H+
2 . carbondioxide
How manyPh —isomers
CH? 'x' of C 8 H 10 (when
A) reacts with hot alkaline KMnO 4 give only aromatic
AlCl 3
|
dicarboxylic
Sum of x+ y=acid
? ? How many isomers'y' of C4 H 8 when reacts with hot alkaline KMnO 4 give
Ph
49. carbondioxide
3 . How many groups
Sum of x+ y= ?
582
? are o p director in the electrophilic aromatic substitution ?

3 . (i)
How—NHmany groups are o(ii)p director
—COH in the electrophilic
(iii) —Naromatic
== O substitution
(iv) ?—COOH
2
O O
(i) —NH 2 (ii) —COH || (iii) —N == O (iv) —COOH||
(v) —OMe (vi) —O —OC— Me (vii) —Et (viii) —O C— NH — Me
Subjective Problems
(ix) —N == NH 2
(v) —OMe
(x) —SO 3 H ||
(vi) —O — C— Me (vii) —Et
||
(viii) — C— NH — Me
(ix) —N == NH 2 (x) —SO 3 H

50.
1.
https://t.me/studyzee
OH
OH
(mild
S Y N T HE SI Z I NG T HE M AT- basic
E RIA L 705
condition)
dil.HNO3 (1) Sn|HCl
A + B C D
15.52 e widely used antioxidant and food preservative
(2) called
NaNOBHA (butylated hydroxyanisole) is actually a mixtur e of 2-tert-butyl-
2/HCl
More Less
4-methoxyphenol and 3-tert-butyl-4-methoxyphenol. BHA is synthesiz ed from p-methoxyphenol and 2-methylpropene. (a) Suggest how
volatile volatile
this is done. (b) Another widely used antio xidant is BHT (butylated hy droxytoluene). BHT is actually 2,6-di- tert-butyl-4-methylphenol,
and the raw materials used in its pr oduction are p-cresol and 2-methylpropene. What reaction is used here?
Double bond equivalent of D is :
2. How many isomers 'x' of C8 H 10 when reacts with hot alkaline KMnO 4 give only aromatic
S Y N Tdicarboxylic
HE SI Z IacidNG? How TH many
E M isomersAT E 'y' RIof
A CL4 H 8 when reacts with hot alkaline KMnO 4 give

51.
carbondioxide
15.53 2-Methylnaphthalene can?
be synthesiz ed from toluene through the following sequence of reactions. Write the structure of each
intermediate.Sum of x+ y= ?
3 . How many groups O O are O
o p director in the electrophilic aromatic substitution ?
H2NNH2, KOH
Toluene + AlCl3
A (C11H12O3) heat
B (C11H14O2)
(i) —NH 2 (ii) —COH (iii) —N == O (iv)
—COOH
SOCl 2
O AlCl3 NaBH O
C (C11H13ClO) || D (C11H12O) E (C11H14O) 4
||
(v) —OMe (vi) —O — C— Me (vii) —Et (viii) — C— NH — Me
(ix) —N == NH 2 (x)H SO
2
H H ) NBS G (C11H12Br) NaOEt
—SOF3(C4
11 12
heat light EtOH,
heat

https://t.me/studyzee
52.
the https://t.me/studyzee
15.54 For each of the following questions, please pr ovide a route that could reasonably be expected to conv ert the starting material into
nal product. In each case, more than one
solve the problem.
reaction is required, and reactions you have learned in previous chapters may be needed to

(a)

NO2

(b)
O
Br
 S Y N T HE SI Z I NG T HE M AT E RIA L 705

15.52 e widely used antioxidant and food preservative called BHA (butylated hydroxyanisole) is actually a mixtur e of 2-tert-butyl-
4-methoxyphenol and 3-tert-butyl-4-methoxyphenol. BHA is synthesiz ed from p-methoxyphenol and 2-methylpropene. (a) Suggest how
this is done. (b) Another widely used antio xidant is BHT (butylated hy droxytoluene). BHT is actually 2,6-di- tert-butyl-4-methylphenol,
and the raw materials used in its pr oduction are p-cresol and 2-methylpropene. What reaction is used here?

S Y N T HE SI Z I NG TH E M AT E RI A L
15.53 2-Methylnaphthalene can be synthesiz ed from toluene through the following sequence of reactions. Write the structure of each
intermediate.

O O O
H2NNH2, KOH
Toluene + AlCl3
A (C11H12O3) heat
B (C11H14O2)

SOCl2 AlCl3 NaBH4

C (C11H13ClO) D (C11H12O) E (C11H14O)

H2SO4 NBS NaOEt

F (C11H12) G (C11H12Br)
heat light EtOH,
heat

15.54 For each of the following questions, please provide a route that could reasonably be expected to conv ert the starting material into
the nal product. In each case, more than one reaction is required, and reactions you have learned in previous chapters may be needed to
solve the problem.

(a)

NO2

(b)
O
Br

(c)

15.55 For each of the following, identify the product (represented by A, B, and C) that would be formed thr ough the indicated
sequence of steps from the given starting material.

(1) Cl
AlCl3 (1) ,∆
(a) A (c)
(2) HNO 3, H2SO4 C
(3) O 3 (2) H 2, Pd/C
(4) Me 2S (3) Br 2, FeBr 3
(5) NaBH 4; H3O+

(b) (1) KMnO 4, HO–

(2) LiAIH 4 in Et2O
(3) H 2O/H2SO4 B
(4) KOt-Bu, t-BuOH
(5) NaH, Mel