JEE MAIN, ADVANCED 2022

#1

DPP NO. (JEE MAIN+ADVANCED)

Max Marks: 52 Max Time: 90 Mins

Answer the following:

]
1. C6H5COOH + CH3MgI

TB
(A) C6H5COOMgI (C) Both A & B
(B) CH4 (D) None

Br

[II
NA
ether
+ Mg
RA

2. F
Br MgBr
IN

(A) (C)
MgBr
CH

F
SA

(B) (D) F

Page No. 1
3. The reactivity order of CH3MgBr with the following compounds is:
OH

H3C CH3
C

(I) (II) O

H3C C Cl

(III) CH3 – Cl
(IV) O

]
(A) I > IV > II > III (C) I > II > IV > III

TB
(B) II > I > IV > III (D) IV > II > I > III

[II
(i) Et2O
H3C CH CH2 + (CH3)2CHMgBr
(ii) H2O

4. O
CH3
NA
H3C CH CH2 HC

(A) H3C (CH2 )4 CH2 OH CH3

(C) OH
H3C CH CH2 CH3
H3C CH CH CH CH3
RA

(D) CH(CH3)2
(B) CH3

Cl CH2 C OEt + 2CH3MgI Followed Product

by H2O
IN

5. O
What is the product?
CH3
CH

H3C CH2 C OEt

HO CH2 C CH3

(C) O
(A) OH CH3
SA

CH3
Cl CH2 C CH3
Cl CH2 C OEt

(D) OH
(B) OH

Page No. 2
 Mg Y
2 H2C CH CH2 Cl X ( H2C CH CH2)2CH OH + H3C CH2 OH
6. Ether
In the above chemical reaction, Y may be:
(A) Ethyl formate (C) Isopropyl methanoate
(B) Methyl formate (D) Ethanoyl chloride

H2C CH2 I

CH2 C Cl
(i) Mg / Ether
Product
O

]
TB
7. F
The final product of the reaction is:

[II
O
H2C CH2 MgI

CH2 C Cl
NA
O
RA

(A) F (C) MgF

O
H2C CH2 MgI

CH2 C Cl
IN

O
CH

(B) MgF (D) F

SA

Page No. 3
8. Analyse the following reaction:
1 CH3MgX 1 CH3MgX 1 CH3MgX
HOCH2CH2COCH2CH2CO2Et P Q R if
a is EtO C CH2 CH2 C CH2 CH2OMgX

O O
CH3

b is EtO C CH2 CH2 C CH2 CH2OMgX

O OMgX
c is H3C C CH2 CH2 C CH2 CH2OMgX

O O
CH3

]
TB
d is H3C C CH2 CH2 C CH2 CH2OMgX

OMgX O
Which is incorrect?
(A)
(B)
P is a
Q is c
(C)
(D)
[II
R is not d
Q is b
NA
9. Match List–I & List–II and select the correct code:

List-I
+
RA

H3O
(a) RMgX + HCHO adduct n-carbon
+
H3O
(b) RMgX + (CH2)2O adduct n-carbon
+
H3O
(c) RMgX + CO2 adduct n-carbon
+
IN

H3O
(d) RMgX +Ph C N adduct n-carbon
CH

List-II
(i) Ketone
(ii) 1º Alcohol (n+1) carbon
(iii) Acid (n+1) carbon
SA

(iv) 1º Alcohol (n+1) carbon

Page No. 4
 Code i ii iii iv
A a d b c
B d a c b
C d b a c
D b a c d

10. Match List–I & List–II and select the correct code:
List-I List-II
(a) RMgI + Acetonitrile (CH3CN) (i) Alkanone

]
(b) RMgI + Carbon disulphide (ii) Ester

TB
(c) RMgI + Ethyl chloroformate (iii) 1º Alcohol
(d) RMgI + Oxirane (iv) Dithionic acid

Code
A
i
c
ii
b
iii
a
iv
d [II
NA
B a d b c
C c d b a
D a c d b
RA

O
IN

1 mole H3C Mg X
+ H2O
CH

O
SA

11.
The product is:

Page No. 5
 OH

OH
O

O O
(C)
(A)
O

]
TB
O
(B) (D) All of these

12. The reaction, [II

NA
Et2O
BrCH2CH2CH2Br + Mg Produce mainly:

(A) CH3CH2CH3 (C)

RA

(D) CH3CH=CH2
(B) BrMgCH2CH2CH2MgBr

13. The order of reactivity of alkyl halide in the reaction

R–X + Mg RMgX is:
IN

(A) RI > RBr > RCl (C) RBr > RCl > RI
(B) RCl > RBr > RI (D) RBr > RI > RCl
CH

Mg Mg (1 eq.)
Br CH2 C C CH2 Br BrMg CH2 C C CH2 MgBr Product
(excess) Et2O
14. Et2O

The major product is:

SA

(A) Br–Mg–CH2–C=C–CH2–Br (C) –(CH2–C=C–CH2) n

(B) Cyclobutyne (D) CH2=C=C=CH

Page No. 6
15. One conversion into Grignard followed by treatment with ethanol, how
many alkyl halides (excluding stereoisomers) would yield 2-methyl butane?
(A) 2 (C) 4
(B) 3 (D) 5

16. How many litres of methane would be produced when 0.595 g of

CH3MgBr is treated with excess of C4H9NH2?
(A) 0.8 litre (C) 0.112 litre
(B) 0.08 litre (D) 1.12 litre

]
17. How many litres of ethene would be produced when 2.62 g of vinyl

TB
magnesium bromide is treated with 224 ml of ethyne at STP?
(A) 0.224 litre (C) 0.448 litre
(B) 0.08 litre (D) 1.12 litre

MgBr OH
[II
N A
+ A

18.
RA

(B)
(A)
OH O Ph
IN
CH

(C) (D)
SA

Cl
1 equivalent Mg D2O
X Y
ether

19. Br

Page No. 7
 Y is:
Cl D

(C) D
(A) D
D

(D) None of these

(B) Br

20. Compounds are shown with the no. of RMgX required for complete
reaction, select the incorrect option:

]
(A) CH3COOC2H5 1

TB
(B) CH3COCl 2
(C) HOCH2COOC2H5 3
OH

[II
NA
CHO

(D) COOC2H5 4
RA

21. What will be the order of reactivity of the following carbonyl compounds
with Grignard’s reagent?
H H3C
IN

C O C O
(I) H (III) H3C
H Me3C
CH

C O C O
(II) H3C
(IV) Me3C
SA

(A) I > II > III > IV (C) II > I > IV > III
(B) IV > III > II > I (D) III > II > I > IV

Page No. 8
 (i) Mg
(R)-2-Bromooctane X
(ii) CO 2
+
22. (iii) H
X is:
C6H13 C6H13

H3C * COOH HOOC * CH3

(A) H (B) H
(C) A and B both (D) None of these

23. In which one of the following reaction products are not correctly
matched in?

]
+
H

TB
(A) RMgX + CO 2 Carboxylic acid

(B) RMgX + C 2H5OH Alkane

(C) RMgX + CH3CH2Cl Alkene

[II
RMgX + Ether
(D) Cl O

24. The number of moles of grignard reagent consumed per mole of the
A
compound is:
HO COOEt
N
RA

O
(A) 4 (C) 3
(B) 2 (D) 1
IN

25. Select the correct statement:

(A) 1,4-dibromobutane react with excess of magnesium in ether to
generate di-Grignard reagent.
CH

(B) 1,2-dichlorocyclohexane treated.

(C) Vicinal dihalides undergo dehalogenation to give alkene when
heated with Zn dust or Mg.
SA

(D) 1,3-dichloropropane by treatment with Zn dust or Mg forms

cyclopropane.

Page No. 9
 O

H3C C CH3 +
Br2 Mg H
H3C CH CH2 (X) (Major)
∆ Dry ether NH4Cl ∆
26.
End product of above reaction is:
OH
CH2
H2C CH CH2 C CH3

(A) H2C CH CH2 C CH3

(C) CH3
H2C CH CH2 CH CH2 OH
H2C CH CH C CH3

(B) CH3 (D) CH3

]
TB
OEt
MgBr + Followed Product
H C OEt +
H3O
OEt
27.
O

C
Ethyl ortho formate

CH3 [II CH O
NA
(C)
(A)
CH CH3
CH2CH O

(B) (D) HC O
RA

Br

1.Mg / ether
IN

+ Product(s)
2. H3C CH CH2 CH 3.H3O

28. OH O
Select the product from the following:
CH

H3C CH CH2 CH H3C CH CH2 CH

SA

I: II: OH O III: OH OH
(A) III (C) I, II
(B) I, III (D) II, III

Page No. 10
29. Order of rate of reaction of following compound with phenyl magnesium
bromide is:
O O O

(I) Me C Cl (II) Me C H (III) Me C O Et

(A) I > II > III (C) III > I > II

(B) II > III > I (D) II > I > III

30. Select the correct order of decreasing reactivity of the following

compounds towards the attack of Grignard reagent:
(I) Methyl benzoate (III) Benzoyl chloride

]
(II) Benzaldehyde (IV) Acetophenone

TB
(A) II > III > I > IV (C) III > II > IV > I
(B) I > II > III > IV (D) II > IV > I > III

[II
A
CH3MgX
O
NH4Cl
N
31.
Product is:
(A) Enantiomer (C) Meso
RA

(B) Diastereoisomer (D) Achiral

CH3MgBr
H3C C CH2 CH2 CH2 Cl A
IN

∆
32. O
A is:
CH

CH3 CH3

H3C C CH2 CH2 CH2 Cl

(C) O CH3
H3C CH3
(A)
SA

OH

H3C C CH2 CH2 CH2 CH3

O
(B) O
(D) H3C

Page No. 11
 O O
(i) CH3MgBr (one mole)
H3C C CH2 CH2 COCH2 CH3 + A
33. (ii) H3O
A formed in this reaction is:
OH O

H3C C CH2 CH2 COCH2 CH3

(A) CH3
O O

(B) H3C C CH2 CH2 C CH3

H3C O
O

]
(C)

TB
H3C
CH3 CH3

H3C C CH2 CH2 C CH3

(D) OH OH

[II
NA
34. Select the correct order of reactivity towards Grignard reagent for
nucleophilic attack:

O O O
RA

(A) R C O C R < R C H
Cl CH2 C H
H > 3C CH2 C H

(B) O O
O O
IN

H3C C O NO2 < H3C C O

(C)
CH

O O

(D) R C OR > R C NH2

SA

Page No. 12
35. In the reaction sequence:
O

(i) CH3MgBr / CuCl

+ (X) Major + (Y)
(ii) H2O / H

(X) & (Y) respectively are:

OH O H3C OH
H3C OH

CH3

]
, ,

TB
(A) CH3 (C) OH CH3
O H3C OH HO CH3 O

CH3

(B) CH3
,

(D)
[II ,

CH3 OH
NA
(2)
O OH
RA

O (3)
H RMgX (2 moles)
IN

H
S

C
CH

CH
36. (4)
Deprotonation will occur from the following positions:
SA

(A) 1, 2 (C) Any two positions

(B) 1, 3 (D) 1, 4

Page No. 13
 Br

Mg (i)14 CO 2 NaHCO3
(A) + (B) (C) gas
(ii) H / H 2O

37.
Product C is:
(A) CO (C) CO2
(B) 14CO2 (D) A mixture of 14CO2 and CO2

38. Which of the following is incorrect?

O O

CH3MgX
C H3C C OC2H5

]
(1 eq)
(A) Cl OC2H5

TB
O
OC2H5
C2H5MgX
H3C C OC2H5 H3C C OC2H5
(1 eq)
(B) OC2H5

(C) CH3MgX + C
S

S
H3O
+
H3C
S

C [II
SH
NA
O O
+
H3O
(D) CH3MgX + C O H3C C OH
RA

39. Which reaction gives 1º aromatic amine as major product?

Br

Mg / ether NH3
IN

(A)
Br

Mg / ether NH3
CH

(B) F
Br

Mg / ether NH3
SA

(C) F

Page No. 14
 Hg(OAc)2
Ph
(D) NH3 / NaBH4

O
+
H3O
CH3MgBr + CH2 CH C H
40. Product (1, 4 addition)
.

It is:
OH

H2C CH C H

(A) CH3
H2C CH CH CH3

]
TB
(B) OH
(C) CH3CH2CH2CHO
(D) None

[II
NA
O O
CH3MgBr(1 eq.)

O
RA

41.

OH OH

O O
IN

O
(A) (C)
CH

O
O O
SA

(D)
(B)

Page No. 15
 (i) Br 2
H2C C O C4 H8 O
(ii) CH 3MgBr
42. (2 equi)
O
CH3
O

(A) CH3
(C) H3C
O

(B) H3C CH3 (D) All of these

NH4Cl RMgX
RMgX + CH3CN (A) (B)
43. NH4Cl

]
(A) 10 ROH (C) 30 ROH

TB
(B) 20 ROH (D) Alkene

[II
CH3MgCl
H3C CH CH2 H2O

44. O
H3C CH CH2OH H3C CH CH3
NA
(A) CH3 (C) CH3
H3C CH CH2 CH3

(B) OH (D) HO CH2 CH2 CH2 CH2 OH

RA

45. The reaction of 1 mole each of p-hydroxy acetophenone and methyl

magnesium iodide will give:
O
IN

CH4 + IMgO C CH3

(A)
CH

H3C O C CH3

(B)
SA

OMgI

H3C C OH

(C) CH3

Page No. 16
 MgI

H3CO C CH3

(D)

r1
+ PhMgBr PhCH2CH2OH
46. (i) O
r2
+ PhMgBr PhCH2CH2CH2OH
(ii) O

]
(A) r2 > r 1 (C) r1 = r2

TB
(B) r1 > r2 (D) r1 = 2r2

47. How
given compound?
SH O
[II
many moles of Grignard reagent will be required by one mole of
NA
HO C OEt

C Cl
RA

H2C CH2 O

Cl
(A) 7 (C) 8
IN

(B) 6 (D) 5
CH

48. Consider the given organometallic compound:

(I) (CH3)2Hg (III) (CH3)2Mg
(II) (CH3)2Zn (IV) CH3Li
SA

The correct decreasing order of ionic character is:

(A) I > II > III > IV (C) I > III > II > IV
(B) II > I > III > IV (D) IV > III > II > I

Page No. 17
 (i) CH3MgBr
O + P
(ii) H3O

H3CHC CH C CH3

(i) CuI, CH3MgBr

+ Q
49. (ii) H3O
OH O

P is H3CHC CH C Me ,Q is H3C CH CH2 C CH3

(A) Me CH3
O OH

P is H3C CH CH2 C CH3 ,Q is H3CHC CH C Me

]
(B) CH3 Me

TB
P is H3C CH CH C(CH3)2 ,Q is H3C CH CH2 C CH3

(C) OH CH3 O
P is H3C CH CH2 C CH3 ,Q is H3C CH CH C(CH3)2

(D) CH3 O
[II OH
NA
For Q. No. 50 to 52
Consider the given reaction and answer the following questions:
COOCH3
RA

MeMgBr
Products
(excess)
IN

O OCH3

O SH
CH

50. No. of RMgX consumed in the reaction is:

(A) 4 (C) 6
SA

(B) 5 (D) 7

Page No. 18
51. How many product will be formed in given reaction (excluding stereo)?
(A) 2 (C) 4
(B) 3 (D) 5

52. Which of the following reaction will give the same Hydrocarbon formed
as one of the product in the above reaction?
(A) EtMgBr + Me OH (C) MeMgBr + Ph OH

(B) PhMgBr + Me OH (D) MeMgBr + H3C CHO

]
TB
[II
NA
RA
IN
CH
SA

Page No. 19
 ANSWERS

1. C 27. C

2. D 28. C

3. C 29. A

4. C 30. C

5. D 31. A
6. A 32. C

7. D 33. C

8. B 34. B

]
TB
9. B 35. B

10. D 36. A

11. A 37. C

12.

13.
C
A
38. B

39. B [II
NA
14. D 40. C

15. C 41. D
16. C 42. A
RA

17. C 43. C

18. A 44. B

19. D 45. A
IN

20. A 46. B

21. A 47. A
CH

22. C 48. D

23. C 49. C
SA

24. A 50. C

25. D 51. C
26. B 52. C

Page No. 20
 JEE ADVANCED, MAIN 2022

#2

DPP NO. (JEE MAIN+ADVANCED)

Max Marks: 48 30 Minutes Test

Passage: (Q1 to Q12)

]
An important route to synthesize unsymmetrical ether is Williamson ether

TB
synthesis. This reaction is an example of Nucleophilic substitution reaction
(SN2 Reaction). It involves the reaction generally between alkyl halide and
alkoxide ion. 1° Alkyl halide and 1° Alkoxide ion give the best yield of ether
during this reaction.

O CH3
[II
NA
1. Best method to prepare is the combination of:

KOH CH3I Cl
OH Na
(C) MeOH
RA

(A)
Na CH3I
OH

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

IN

NaH Me-I
H OH
CH

2.
Identify the final product:
SA

H OMe MeO H

(A) (B)

Page No. 1
 H OMe
(D) None of these
(C)

3. Identify product:
EtO- + Ph-CH2-Cl

(A) Ph O (C) H2C CH2

O
(B) Ph O (D) Ph

4. Which of the following is an appropriate set of reactants for the

]
preparation of 1-Methoxy-4-nitrobenzene?

TB
Br ONa

+ CH3Br

(A)
ONa
+ CH3ONa (C)
[II
O2N
NA
ONa

+ EtONa
+ CH3Br
(D) O2N
RA

(B) NO2

5. Suitable combination of reactant to prepare:

IN

O
Ph
CH

Br
ONa
(A) Ph +
ONa
SA

Br

(B) Ph +

Page No. 2
 –
O
Br
(C) Ph +

–
O
Br
(D) Ph +

CH3

H OK
EtBr
Product
H CH3

]
6. Et

TB
Correct stereochemical relationship between reactant and product will
be:
(A) Enantiomer (C) Structural Isomer
(B) Diastereomer (D) None of these

(A)
O
[II
7. Which of the following can’t be prepared by Williamson ether synthesis?
NA
(B) O

O
RA

(C)

(D)
IN

8. Incorrect statement regarding the Williamson ether synthesis is:

(A) Less hindered halide is used in this reaction.
CH

(B) Less hindered alkoxide ion is used in this reaction.

(C) Mechanism of reaction will be SN2.
(D) More hindered halide is used in this reaction.
SA

9. Which of the following ether is not synthesized by Williamson ether

synthesis?

Page No. 3
 O CH3 O

(A) (C)

O O

(B) (D)

]
10. RO-Na+ + R’-L ROR’ + Na+L-

TB
Rate of reaction will be maximum when L is:
(A) CF3SO3- (Triflate Ion)

(B)
(C)
H3C

Br- [II
SO 2- (p-Toluene sulphonate)
NA
(D) I-

11. Identify the products:

KH TsCl
A OH B
RA

C
IN

12. The best combination for the preparation of ether by Williamson’s

synthesis are:
CH

(A) (CH3)3CBr and CH3Ona (C) CH3Br and (CH3)3CONa

(B) (CH3)3CBr and CH3OH (D) CH3Br and (CH3)3COH
SA

Page No. 4
 ANSWERS

1. B
2. A
3. B
4. C
5. D
6. D

]
7. C

TB
8. D
9. CD
10. A

11. (A): OK; (B):

[II
OK; (C): OTs
NA
12. C
RA
IN
CH
SA

Page No. 5
 JEE ADVANCED, MAIN 2022

#3

DPP NO. (JEE MAIN+ADVANCED)

Max Marks: 28 20 Minutes Test

Identify the missing structure in each reaction:

]
Cl

TB
15 % NaOH

1. NO2
1600C

[II
NA
Cl

O2N NO2

H2O
RA

(A) Acid

2. NO2
Br
IN

NO2

CH3O-
CH
SA

3. NO2

Page No. 1
 Br

NO2

CH3O-

4. Br

Br

NO2

H3C CH2 NH2 –

(A) HO (B)

]
TB
5. NO2

F OH

[II
NA
– +
HO H
(A)
mesenheimer
complex
RA

NO2
6. NO2

KOH /
IN

7. NO2
CH
SA

Page No. 2
 NO2

KOH / ∆

Br

8. Br

CH3

KNH2
(A)

]
liq. NH 3 (major)

TB
9. Cl

OCH3

Cl [II
NA
KNH2
(B)
liq. NH3 (major)
10.

Br
RA

- +
CH3ONa
(A)
IN

11. NO2
CH

Energy profile diagram of given reaction is?

SA

Page No. 3
12. Most reactive towards SN–Ar

Br Br

NO2

(A) NO2 (C) NO2

Br
Br

]
TB
NO2

(B) NO2
(D)

[II NO2
NA
13. Steps involve in given reaction
RA

F OH

–
HO
IN

NO2 NO2
CH

(A) Addition-substitution (C) Elimination-Addition

(B) Addition-Elimination (D) Substitution-elimination
SA

14. Most reactive towards SN–Ar is

Page No. 4
 F Cl

(A) NO2 (B) NO2

Br I

]
TB
(C) NO2 (D) NO2

[II
NA
RA
IN
CH
SA

Page No. 5
 ANSWERS
OH OCH3

NO2

1. NO2 3. NO2

OH

]
OCH3

TB
O2N NO2
NO2

2.
NO2
(picric acid)
4.
[II
Br
NA
+
H2N CH2 CH3 HN CH2 CH3

NO2 NO2
RA

A= ,B=

5. Br Br
IN

F OH OH
CH

7. NO2
SA

+
N
– –
6. O O

Page No. 6
 NO2 OCH3

Br 10. NH2

8. OH
CH3

]
9. NH2

TB
Br OCH3

11.
[II
Intermediate is: NO2
NA
12. A
13. B
14. A
RA
IN
CH
SA

Page No. 7