Chemistry

TARGET : JEE (Main + Advanced)

ENTHUSIAST COURSE
(SESSION : 2021-22)

RACE (BOOKLET) # 21 to 35
ORGANIC

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 JEE (Main + Advanced) 2022
JEE (Main + Advanced)
ENTHUSIAST 2022
COURSE
ENTHUSIAST COURSE
RACE # 21 ORGANIC CHEMISTRY
M.M. : 33 TIME : 20 Min.

1. 
:

-I 
- II [4, –1]

O3
(A) X 
Zn / H2O
 CH3  CH2CHO (P)

O
H
O3 O+ O
(B) X   + (Q) Ph – CH = CH – CH3
ZnH2O
H
O

O3
(C) X 
Zn / H O
 PhCHO + CH CHO
3 (R)
2

O
O3
(D) X 
Zn / H2O
 (S) CH3 – CH2 – CH = CH – CH2 – CH3
O

2. : 
2 
Br 2  [3, –1]
: 
(A)     
(B)     
(C) 
(D)   

CH3
O
3. CH 3 – CH = CH – C – CH = CH – CH3  3
Zn  H O

2
 [3, –1]



(A) 2 (B) 3 (C)  (D) 1

OC / R # 21-35 (Book) H-1/41

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ENTHUSIAST COURSE

CH3

 
O3
CH3 
4. [3, –1]
Zn / H2O / 


:

O O CHO
CH2
(A) CHO (B) CH3 – C – C – CH3 (C) CH3 – C – C – H (D)
CHO
CHO O O

3 O
5. A 
Zn
2CH3 – CHO + CO2 [3, –1]


A 
:
(A) CH2 = CH – CH = CH – CH3 (B) CH3 – CH = C = C = CH – CH3
(C) CH3 – CH = CH – CH = CH2 (D) CH3 – CH = C = CH – CH3
6.  [4, –1]

O 3

Zn / H O

2

O CHO
CH2
(A) HCHO (B) CH3 – C – CH3 (C) CH3 – C – CHO (D)
O CHO

O3 O
7. X 
Zn / H2O
 H + O+ CHO [3, –1]
H
O

‘X’ 

(A) (B)

(C) (D)

8. [A] 
HCHO 
CH3 – C – CHO 
A
O

: [3, –1]
(A) 3 (B) 4 (C) 2 (D) 5

H-2/41 OC / R # 21-35 (Book)

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ENTHUSIAST COURSE

 O
(1) O3
9. X  + HCHO [3, –1]
C10H12 ( 2) Zn / H2O O
O
X 
:

CH 2 CH 2 CH2 CH2
CH 2
(A) O (B) (C) (D)
CH2 O CH2
CH2

10. 

3 O O 3
(1) 
Zn / H O
 (2) 
Zn / H O
 [4, –1]
2 2

O3 O3 O3
(3)   (4)   (5)  
Zn / H2O Zn / H2O Zn / H2O

FILL THE ANSWER HERE

1. 2. 3. 4.

5. 6. 7. 8.

9. 10.

OC / R # 21-35 (Book) H-3/41

 JEE (Main + Advanced) 2022
JEE (Main + Advanced)
ENTHUSIAST 2022
COURSE
ENTHUSIAST COURSE
RACE # 22 ORGANIC CHEMISTRY
M.M. : 39 TIME : 30 Min.

1. 
-I 
-II [8, –0]
  
H 2 (1 eq.)
(A) Ni (P)     

H –Pd
(Q) 
Br2 /     
2
(B) CH3–C C–CH3 BaSO
4

Alk. KMnO4
(C) 0º C (R)  

Me
H Cl NaI
(D) Acetone (S)     
H Cl
Me

(T)      

2. : HI 
[3, –1]
: HI
(A)       
(B)    
(C) 
(D) 
3. 
'Q'  [3, –1]
Cl
Mg (i) CO2
1 eq.
P + Q
(ii) H

Br
O CH3
COOH COOH COOH C

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

COOH Br Cl Cl
4.           
 [3, –1]
CH=N–NH–C–NH2 N–NH–C–NH2
(A) O (B) O

CH=N–C–NH–NH2 CH=N–NH–C–NH2
(C) O (D) O

H-4/41 OC / R # 21-35 (Book)

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ENTHUSIAST COURSE

NO2

5. Na in
X Y . Y  [3, –1]
liq. NH3 LAH

NH2 NH2 NO2 NH2

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

6.  [3, –1]

(1) H /Pd-BaSO (1) Li / N H3
(A) CH3—C C—CH3 (2) Br2 /CCl 4 (B) C2H5—C C—C2H5
(2) Br2 /CCl4
2 4

O
(1) H 2/Pd-BaSO 4 Al(OCHMe2)3
(C) CH3—C C—CH3 (D) CH3—CH
(2) dil. KMnO 4
(1) (2) (3)
7. H2N–NH–C–NH2 ; [X]  [4, –1]
[X] O
(A) [X] 
(semicarbazone) 
(1)
(B) N 
(C) [X] 
(D) [X] 
8 
9 

Keq 
  
Keq
O
HCHO > R–CHO > R – C – R 
CCl3–CHO, CF3–CHO, HCHO,

O O O

Ph – C – C – C – Ph , O, O      

O
O

Keq >1 

8. 
Keq  [3, –1]

(1) C6H5COCH3 (2) (3) (4)

(A) 3 > 2 > 1 > 4 (B) 2 > 1 > 3 > 4 (C) 3 > 1 > 2 > 4 (D) 4 > 2 > 1 > 3

OC / R # 21-35 (Book) H-5/41

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OH OH
| |
9. CCl3 + H2 O  CCl 
3 C  OH X , + H2O CH3  C  OH Y [3, –1]
| |
H CH 3

X 
Y 
(A) X = 0.2 %, Y = 99.95 (B) X = 99.9%, Y = 0.2%
(C) X = 0.2%, Y = 0.2% (D) X = 99.9%, Y = 99.9%
10. 
2º  [4, –1]
O O
LAH (i) LAH
(a) R—C—R (b) CH3—CH2—C—NH2
(ii) NaNO2/HCl

O
(i) CH3MgX(excess)
(c) H—C—OR +
(d) H3C—HC—CH2 (i) RMgX
+
(ii) H (ii) H
O
O
dil. H2SO4 CH3MgX (excess)
(e) H3C—HC = CH2 (f) CH3—C—Cl +
H

FILL THE ANSWER HERE

1. 2. 3. 4.

5. 6. 7. 8.

9. 10.

H-6/41 OC / R # 21-35 (Book)

 JEE (Main + Advanced) 2022
JEE (Main + Advanced)
ENTHUSIAST 2022
COURSE
ENTHUSIAST COURSE
RACE # 23 ORGANIC CHEMISTRY
M.M. : 41 TIME : 35 Min.
1. - I 
- II [4, –1]
 
(i) RCO3H
(P)  +
(1) 
(ii) H3O
(i) OsO4
(Q)  (2) 
(ii) H O+
3
–
(R) CH3–CH–CH2–CH3 EtO / (3) 
Br
O
(S) CH3–CH2O–C–CH3 (4) 
Code :
P Q R S
(A) 4 2 1 3
(B) 4 3 2 1
(C) 4 1 2 3
(D) 4 3 1 2
2. : CHCl3 
 CHF3  [3, –1]
: CCl 3 
(back bonding)
(A)       
(B)    
(C) 
(D) 
3.      O
3
/ H2O           
COOH
 [3, –1]
COOH

(A) (B) (C) H2C = CH2 (D)

1. O3
4. 2. H2O
 [3, –1]

O O O O O O O O

(A) HO OH (B) H OH (C) H H (D) HO OH

OC / R # 21-35 (Book) H-7/41

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ENTHUSIAST COURSE

Cl
1. Alcoholic KOH D2O
5. X Y.
2. NBS , 3. Mg(D.E) O3/Zn


Y  [3, –1]
(A) O = CH–CH2 – CH2–CH2–CH2–CH=O (B) O = CH– CH –CH2–CH2–CH2 – CH=O
D
(C) O = CH–CH2– CH –CH2–CH2–CH=O (D) O = CH– CH –CH2–CH2– CH –CH=O
D D D

6.  [3, –1]

O
O O O
H—C—H ; CH3—C—C2H5 ; + CHO
I II |
(2 mole) (1 mole) O CHO
(1 mole) (1 mole)

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

7.

 [4, –1]

(A) H3O+ ; 

H2SO4/ (B) O3 / Zn ; LAH ; 
H2SO4 / 

(C) O3 / Zn ; H2(Ni) ; 

H3PO4 /  (D) B2H6 + H2O2 + NaOH ; Al2O3

08  09 
 
Me
Me Me
(I) (II) (III) (IV)
Me
Me Me Me
Me
Me Me
(V) (VI) (VII) (VIII)
Me
Me Me Me Me

Me Me

(IX) (X)
Me

8.     Zn


 
       
 [4, –1]
(A) (V) (B) (I) (C) (III) (D) (VI)
H-8/41 OC / R # 21-35 (Book)
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9. 
Zn 
 [4, –1]
(A) (III) (B) (IX) (C) (X) (D) (VII)
10.  [9, –3]

(i) O3 (i) O
3
(i) CH2=CH2 
(ii) Zn / H 2O
 (ii) CH3–CH=CH–CH3 
(ii) Zn / H 2O


(i) O
3
(iii) CH3–CH=CH2 
(ii) Zn / H 2O


FILL THE ANSWER HERE

1. 2. 3. 4.
5. 6. 7. 8.

9.

10(i). 10(ii).
10(iii).

OC / R # 21-35 (Book) H-9/41

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JEE (Main + Advanced)
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ENTHUSIAST COURSE
RACE # 24 ORGANIC CHEMISTRY
M.M. : 34 TIME : 30 Min.
1. - I - II [4, –1]
(P) CH3–CH2–CCH (1) 
ZnCl2 + HCl 
O
(Q) (2) 

(R) OH (3) NaOH + I2 

O
(S) (4) 
Code :
P Q R S
(A) 4 3 1 2
(B) 4 1 3 2
(C) 3 2 4 1
(D) 3 4 2 1
O –
Ag(NH 3)+2OH
2. X,X  [3, –1]
CH=O
–
HO HO CO 2 O
(A) (B) (C) (D)
CO 2H CH=O –
CH=O CO2

3. A (C7H15Br) – B + C ( 
 C7H14) [3, –1]
OMe/
H2(Ni)

3-  

A 
Br

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

Br Br Br

4. SN1  [3, –1]

Cl
H3C—O—CH2— Cl H3 C—N—CH2— Cl CH 2—Cl
(P) H
(Q) (R) (S)

(A) P > Q > R > S (B) R > Q > P > Q (C) Q > P > R > S (D) Q > P > S > R

H-10/41 OC / R # 21-35 (Book)

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PhCO H 
3 H3O PI3 , 
5. CH2 = CH2    A  B 
(2 eq )
C [3, –1]

C 

(A) CH 2  CH 2 (B) CH2=CH2 (C) (D) CH 2  CH 2

| | | |
OH I I I

6.  [4, –1]

CH3
Br H NaI CF3CO3H
A B
Br H 
CH3

(A) B (B) B 

(C) A  (D) B 
7.  [3, –1]

O O
CH3–CH2–C CH3–CH2—C
OH H

(A) (i) LiAlH4 , PBr3 , DMSO /NaHCO3 / (B) (i) R'–OH/H+ (ii) DI-BALH

(C) (i) Ca(OH)2 (ii) (HCOO)2Ca/  (D) (i) LiAlH4 (ii) Cu/300°C


08  09 

alc.KOH
PhCH – CH3 B
Cl aq. O3/Zn
KOH
A C + D
1.CH3MgX
C 2.H+ A

8.  [3, –1]

(A) C  D 
(B) A 
(C) B , 
(D) A , 3º 
9.  [3, –1]
(A) C D 
(B) A B 
(C) C A 
(D) 
OC / R # 21-35 (Book) H-11/41
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10.   

CH3–CHO   

[4, –1]

(i) Cu/573 K (ii)  

(iii) Na/LiqNH3 (iv)  

(v) NaOH/I2 (vi) (vii) H/KMnO4/ (viii) H2/Pd

(ix) H/K2Cr2O7/ (x) OH¯/

FILL THE ANSWER HERE

1. 2. 3. 4.
5. 6. 7. 8.

9. 10.

H-12/41 OC / R # 21-35 (Book)

 JEE (Main + Advanced) 2022
JEE (Main + Advanced)
ENTHUSIAST 2022
COURSE
ENTHUSIAST COURSE
RACE # 25 ORGANIC CHEMISTRY
M.M. : 30 TIME : 35 Min.
1. - I - II [4, –1]
 
–
(P) (1) (i) SOCl2 , (ii) (CH3)2Cd , (iii) OH /

–
(Q) (2) (i) SeO2 , (ii) OH , (iii) H+/
CO2H

O
O C – –
(R) CH3–CH = O  (3) (i) O3/Zn, H2O, (ii) OH /, (iii) N2H4 + OH /
C O
O
–
(S) PhCO2H  Ph– C = CH – C –Ph (4) (i) O3/Zn, H2O, (ii) OH /, (iii) NaOH+I2;H+
CH3 O
Code :
P Q R S
(A) 3 4 1 2
(B) 3 2 1 4
(C) 3 4 2 1
(D) 3 2 1 4
Cl2(hv) aq.NaOH
(1 eq.)
X1 Y1
CH3
Cl2(hv) aq.NaOH
2. X2 Y2
(2 eq.)
Cl2(hv) aq.NaOH
(3 eq.) X3 Y3

Y1 
R
Y2
1

Y1 
R
Y3
2

R1 
R2  [4, –1]
(A) PCC (CH2Cl2) ; PCC (H2O) (B) PCC (H2O) ; PCC (CH2Cl2)
(C) 
PCC (CH2Cl2) (D) 
PCC (H2O)

H-13/42 Organic / R # 21-35_(Booklet)

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3.  [4, –1]

O O

(i) LiAlH4
(ii) H3O+

C
O OCH3

CH2OH CH2OH CHO CHO

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

CH2OH CHO CHO COOH

4.  
(A)    
3 
H
2   
1-

-4-
 
  (A)         
:   
O O O O O O
|| || || || || ||
H–C–H , H–C–CH2–C–C–CH3 , CH3–C–CH2–C–H

(A)  [3, –1]

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

5. [4, –1]
O O
Pd/BaSO4 C–H Na
(A) Me–CC–CH2 – C –Cl H2 (B) Me – C  C – Me liq. NH 3

Me Br
Me H Br2
OsO4
(C) (D) CCl4
H OH
Br
OH

6. 
 [3, –1]

OMe
+

(A) Me (B) Et (C) H (D) OMe

H-14/42 Organic / R # 21-35_(Booklet)

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7.  [4, –1]

CH3
(1) CO2
(a) H3C MgBr +
(2) H3O
CH3

O
(1) CH3CH2MgBr
(b)
(2) H2O

CHO
(1) C6H 5MgBr
(c) (2) H 2O

(1) CH3MgCl
(excess)
(d) COOCH2CH3 (2) H2O

MgBr (1) CH2=O

(e) (2) H2O

O
(1) CH3MgBr
(f) (2) H2O

O (1) CH3MgBr
(g) (2) H2O

O (1) (CH3)2CuLi
(h) (2) H 2O
C6H5


08  09 

C4H8O 
 2,4-


H2SO4 
P 
Q 
P 
Q 


8. P  [3, –1]

(A) 
(B) 

(C) 
(D) 

9. Q  [3, –1]

(A) 
(B) 

(C)  CH3MgBr 

CH3–CH3  (D) 

H-15/42 Organic / R # 21-35_(Booklet)

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Me Me
10. CH3– CH –CH=CH–CH=CH– CH –CH3 [4, –1]

X 
A 

X 
B 

(A + B) 

FILL THE ANSWER HERE

1. 2. 3. 4.
5. 6. 7.

8. 9. 10.

H-16/42 Organic / R # 21-35_(Booklet)

 JEE (Main + Advanced) 2022
JEE (Main + Advanced)
ENTHUSIAST 2022
COURSE
ENTHUSIAST COURSE
RACE # 26 ORGANIC CHEMISTRY
M.M. : 37 TIME : 30 Min.

1. 
-I 
-II (      
)
[8, –0]
NaOH
(A) CH3–CHO 
  (P)  NaHCO3


CO2 

(B) Ph–CHO 


 
(i)NaOH
(Q) 
SAE  
(ii)H N

(1) (MeCO) O ,MeCOONa / 

(C) Ph–CHO
2
(2) H3O  / 
   (R)  


(1) NaOH / I
(D) CH3–CHO 

2
  (S) 
(2) H

(T) 

2.
O3

H2O
Lime
 A + B 
Water
  [4, –1]
Excess

+C
-1 : 
"C" 
-1,5-
-2 : A  C R.D.S. 
(A) 
-1 
-2 
-2, -1
(B) 
-1 
-2 
-2, -1 
(C) 
-1 
-2 
(D) 
-1 -2 
O
CCH
X , X 
2 dil. H SO
4 
3. 
HgSO4
 
(i) I2 / NaOH
  [3, –1]

(ii) H

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

Z , Z 
O3/Zn —
4. X 1. OH
+ Y - [3, –1]
2. H

CH2 CH 2CO 2H CH2 CH2

(A) O (B) (C) C=O (D) O
CH2 OH O
O

OC / R # 21-35 (Book) H-17/41

 JEE (Main + Advanced) 2022
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– Ac 2O SOCl2
5. PhCH = O + CH3CH = O OH
X AcONa
Y Z NH3
W ; W  [3, –1]

(A) PhCH = CH – C – NH2 (B) PhCH = CH – CH = CH – C – NH2

O O
(C) CH3CH = CH – C – NHPh (D) PhCH = CH – CH = CH – C – Cl
O O
–
O3 OH
6. X Y Z [3, –1]
Zn I2 + NaOH
+
H


:
C – CH3
(A) X  H3C–C–(CH2)4 – C — CH3 (B) Y 
O
O O
O

OH
(C) Z  (D) X  Y 

7. 
NaOH + CaO,   [3, –1]
O
O O O O
C–OH C–OH
H H OH H
O
Cl
(I) O H
(II)
(III)

(A) I > II > III (B) III > II > I (C) II > III > I (D) III > I > II

08  09 
X (C5 H10 O)          
Y (C5H12O) 
X MnO2 
Z (C5H10O)

8. 
X 
- [3, –1]
(A) 1-
-3- (B) 4-
-2-
(C) 3-
-2-
-1- (D) 2-
-2-
-1-
9. Y  [3, –1]
(A) 
(B) (cerric) 
(C) 
FeCl3 
(D) 

H-18/41 OC / R # 21-35 (Book)

 JEE (Main + Advanced) 2022
ENTHUSIAST COURSE

10. 
CO2 
: [4, –1]

O O
O
O C – OH
C – OH
C – OH
(i) (ii) (iii)
C – OH
O

O O
(iv) O2N – CH2 – C – OH (v) CH 2 – CH 2 – CH 2 – C – OH
OH

FILL THE ANSWER HERE

1. 2. 3. 4.

5. 6. 7. 8.

9. 10.

OC / R # 21-35 (Book) H-19/41

 JEE (Main + Advanced) 2022
JEE (Main + Advanced)
ENTHUSIAST 2022
COURSE
ENTHUSIAST COURSE
RACE # 27 ORGANIC CHEMISTRY
M.M. : 38 TIME : 30 Min.
1. 
-I 
- II [8, 0]
CH=CH–CO2H
(A) (P) NaHCO3 

CH=CH–CH3

(B) (Q) NaOH 

HO

(C) (R) HBr 



(D) CH 2 = CH–CH–CO 2H (S) 

CH3
(T) 
2. 
'X' 
C4H8O3 
NaHCO3 
CO2 
'X' ,
LiAlH4 
'X'  [3, –1]
(A) CH3CH2CHCOOH (B) CH3CHCOOH (C) CH3CHCOOH (D) CH3CHCH2COOH
| | | |
OH Me CH2OH OH
3. 
I2 
NaOH  
[3, –1]
(A) CH3CH2(CHOH) CH2CH3 (B) C6H5CH2CH2OH
CH3
(C) CH3 (D) PhCHOHCH3
OH
4. 
H+  [3, –1]
OH
(A) (B) CO2H
CO2H
OH
CO2H
(C) (D)
CO2H
OH CO2H

5.     [3, –1]

(A)  (B)  (C)  (D) 

H-20/41 OC / R # 21-35 (Book)

 JEE (Main + Advanced) 2022
ENTHUSIAST COURSE

6.  [3, –1]

O O
(i) LiAlH 4 NaOH
(A) Ph – C – CH3 + (B) Ph – C – NH2 Br 2
(ii) H 3O

O O
P4O10 SOCl2 NH3
(C) Ph – C – NH2 (D) Ph – C – O – H

7.  [4, –1]

(A) (B) CH2=O (C) (D) CO2

  

08  09 
 
i) CH3MgBr – (1) O
(P) t-BuO
(i) t-BuOH
(Q) 3
(R) + (S)
ii) H2O (2) H2O/Zn
iii) HBr Major
O

(ii) (R) + 

 

(iii) (S) + NaOH + I2  [T] + [U] 


HgSO 4
(iv) (U) + Ag [V] [W]
dil. H2SO4

8.  (X)

 [3, –1]
–
OH –
[R] + [W] H-COO + (X)
(4 : 1)


OH H H
HO O O
(A) C2 H 5OH (B) (C) CH3COOH (D)
HO OH O O H
H

9.      [3, –1]

Br
(A) P, (B) Q,

(C) R, CH3 – CH2 – CH = O (D) S, H – CHO

OC / R # 21-35 (Book) H-21/41

 JEE (Main + Advanced) 2022
ENTHUSIAST COURSE

10.  [4, –1]

OH

   
Conc.
(i) (1)NBS
(ii) 
H 2SO 4 / 
(2) AlcoKOH / 

O
COOH
Cl
(iii)  
Aq.

KOH
(iv) 
  
OH

(v) 
  
COOH
O

FILL THE ANSWER HERE

1. 2. 3. 4.

5. 6. 7. 8.

9. 10.

H-22/41 OC / R # 21-35 (Book)

 JEE (Main + Advanced) 2022
JEE (Main + Advanced)
ENTHUSIAST 2022
COURSE
ENTHUSIAST COURSE
RACE # 28 ORGANIC CHEMISTRY
M.M. : 32 TIME : 30 Min.

Q.1   [25, 0]

2 Conc . H SO
(1) EtCOCl + EtCOONa  (2) EtCOOH + EtCOOH    4 


(3) 
 (4) 



H 3O NaOH
(5) Me  C  O  C  Me   (6) 
|| ||
O O

(7) Me  C  OMe  EtONa  (8) + MeNH2 

||
O

(9) Ph  C  NH2  Me2 NH  (10) 

||
O
Py
(11) Me  C  Cl  ROH   (12) MeCOCl + EtOK 
||
O
(13)MeCOCl + NH3  (14) Ph – NH2 + MeCOCl 

(15)Ph – NH2 + PhCOCl  (16) PhOH + PhCOCl 

(17)RNH2 + PhSO2Cl  (18) R2NH + PhSO2Cl 

SO2Cl

(19)ROH + KCN  (20) ROH +  X KCN


Me
(Ts – Cl)

(21) 
 (22) NH 3
 


P2O5
(23) Me  C  NH 2 NaOH
 (24) Me – C – NH2 
|| 
O O

PCl5
(25) Me – C – NH2 
O

OC / R # 21-35 (Book) H-23/41

 JEE (Main + Advanced) 2022
ENTHUSIAST COURSE

Q.2 
[4, –1]

OH OCH3
(a) O (b) (c) (d)
OCH3 OCH3
O

C CH
(e) (f) (g) HCO2H (h)

Q.3.  [3, –1]


H3O
CH2(COOEt)2 + (CH2)3Br2 NaO
 Et
 I   II
EtOH 
I 
II

H-24/41 OC / R # 21-35 (Book)

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RACE # 29 ORGANIC CHEMISTRY
M.M. : 25 TIME : 30 Min.
Q.1    [25]
Anhydrous
(1) + 
AlCl3
 (2) + Anhydrous
 
AlCl3

Anhydrous Anhydrous
(3) + 
AlCl3
 (4) + 
AlCl3


Anhydrous Anhydrous
(5) + 
AlCl3
 (6) + PhCH2Cl 
AlCl3


Anhydrous Anhydrous
(7) + CH2Cl2 
AlCl3
 (8) + CH2Cl2 
AlCl3


Anhydrous Anhydrous
(9) 
AlCl3
 (10) + Me  C  Cl 
AlCl3

||
O
Me Me
| Anhydrous
| Anhydrous
(11) + Me  C  C  Cl 
AlCl3
 (12) + Me  C — C  Cl 
AlCl3

| || | ||
H O Me O

Anhydrous Anhydrous
(13) 
AlCl3
 (14) + Me  C  O  C  Me 
AlCl3

|| ||
O O

Anhydrous Anhydrous
(15) + 
AlCl3
 (16) + 
AlCl3


(17) + C – C = C conc
 . H 2SO4
 (18) + C – C – C – OH conc
 . H 2SO4



H
(19) + HNO3 H2SO4 (20) + HNO2 
 Q
HCl + ZnCl2
(21) + CO HCl + ZnCl2 (22) HCN
(2) H3O

(23) + Cl2 (24) + Cl2 FeCl3

h
(25) + Cl2
(excess)

OC / R # 21-35 (Book) H-25/41

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1. 
-I 
-II [8, 0]
+ –
NH2 N2Cl

(A) pH=6.5 (P) 

(B) HNO3
(Q) 
H2SO4

NO2

(C) aq. KOH

(R) 

Cl

O
O–C–Me

(S) 
AlCl3
(D)

OH OH
2. 
1 : (i) PhCO H


3
 [3, –1]
(ii) H3O


 2 : 
Anti 
(A) -1 
-2 
-2, -1
(B) -1 
-2 
-2, -1 
(C) -1 
-2 
(D) -1 -2 
3.    [3, –1]
(A) C6H6 = C6D6 = C6T6 (B) C6H6 > C6D6 > C6T6
(C) C6H6 = C6D6 > C6T6 (D) C6H6 < C6D6 < C6T6
4.   [3, –1]
+
C6H5CH3 C6H6 C6D6 C6 T6 C6H5Br C6H5NR3 C6H5NMe2
A B C D E F G
(A) G > A > B > C > D > E > E (B) G > B > C > D > A > F
(C) G > A > B = C = D > E > F (D) G > A > B > C = D > E > F

H-26/41 OC / R # 21-35 (Book)

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5.  [3, –1]

CH3
H3C CH3
CH 3 CH3 CH3 C

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

H3C
CH3 C C
H3C CH3 H3C CH 3
CH3 CH3

6.  [4, –1]

O
C–Me –
O O NH2–NH2/OH O O
Zn–Hg
(A) HCl (B)
H
C CH3
OH OH O

O O
(i) SeO2
O
N2H4
(C) (ii) MnO2 / C–H (D) H2O2

7.  [4, –1]

NO2 NO2 O


KMnO4 1. KMnO4 ,
(A) O (B)
500ºC 2. CH2OH
O CH2OH

Me Me

Cr2O3 Na
(C) Al2O3 /
(D) Liq. NH3
Me Me
8.  [4, –1]
(A) CH3COCl > (CH3CO)2O > CH3COOEt > CH3CONH2 (
)

(B) CH3–CH2–COOH > > (

)

(C) > > (

)

(D) > > Ph–CH2–COOH (

)

OC / R # 21-35 (Book) H-27/41

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9.  [4, –1]

+
H3 O
(a) + CO + HCl + AlCl3 (b) + HCN + HCl + ZnCl2
(anhydrous)

CH3 CH3 CH3

Chromic (i) SeO2 (i) Cl2 / hv (2 eq.)

(c) Anhydride (d) (ii) MnO2 (e) (ii) steam

10. 
  [4, –1]
O O
(a) –Me (b) –F (c) –NH– C –R (d) – C –NH–R (e) –CN
O O
(f) – C –H (g) –NO2 (h) –Br (i) –CF3 (j) –O– C –CH3
O
(k) – C –OCH3

FILL THE ANSWER HERE

1. 2. 3. 4.

5. 6. 7. 8.

9. 10.
H-28/41 OC / R # 21-35 (Book)
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COOPh

Cl2 / AlCl3
1. [3,–1]

 
COOPh COOPh OCOPh OCOPh

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

Cl Cl
Cl Cl
2. 2 :1  

(A)  
Analgesic (B)  [3,–1]
(C)  (D) 
3.      [3,–1]

H2SO4 (i) m-CPBA Red P + HI

(P) +
(Q) (R)
OH (ii) H3O

  

(A) (R)     6  
(B) (P)       
(C) (Q), CH3MgBr     
(D) (Q) , Na       
4. H–
3º : 2º : 1º = 6 : 4 : 1 

Cl
Cl2
[3,–1]
hv

(A) 3/31 (B) 6/31 (C) 16/31 (D) 16/29

5.  
CH3
H3C CH3
CH 3 CH3 CH3 C

(A) (B) (C) (D) [3,–1]

H3C
CH3 C C
H3C CH3 H3C CH3
CH3 CH3

OC / R # 21-35 (Book) H-29/41

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6.  H
3
O    

: 

CH=CH2 CH=CH2 CH=CH2 CH=CH2

[3,–1]
O NO2 CH3
I II III IV

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

Mg 1. CO2
7. Br A + B [3,–1]
THF 1. H
LiAlH4

C
C      
(A)    5    
(B)  Ph—CHO 
(C)  Ph—CH2—OH 
(D)  PCl3     
8.      
OH
(1) NaOH
+ CHCl3 [3,–1]
(2) H +

OH OH OH OH
OHC CHO CHO
(A) (B) (C) (D)
CHO
CHO

9. 
1-
-3-            
Br

[3,–1]
1-
-3- 
O O
Br2 Cl Zn(Hg) Cl Br2 Zn(Hg)
(A) (B)
FeBr3 AlCl3 HCl AlCl3 FeBr3 HCl

O
Br2 Br2 Cl
Cl Zn(Hg)
(C) (D) FeBr3 AlCl3
AlCl3 HCl FeBr3

H-30/41 OC / R # 21-35 (Book)

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Alc. KOH
10. [4,–1]
H3C
Br
 

FILL THE ANSWER HERE

1. 2. 3. 4.
5. 6. 7. 8.

9. 10.

OC / R # 21-35 (Book) H-31/41

 JEE (Main + Advanced) 2022
JEE (Main + Advanced)
ENTHUSIAST 2022
COURSE
ENTHUSIAST COURSE
RACE # 32 ORGANIC CHEMISTRY
M.M. : 34 TIME : 30 Min.

1.        [3,–1]

Cl
Cl
NaOMe / MeOH
O2N NO2

OMe Cl
MeO MeO
(A) (B)
O2N NO2 O2N NH2

Cl OMe
MeO Cl
(C) (D)
O2N NO2 O2 N NO2

2. 
C=N – NH–  [3,–1]

(A) C6H5NHNH2 (B) (CH3)3N (C) C6H5NHC6H5 (D) 

3.          [3,–1]

+ +
O
:

O O O :–
:–
–
(A) (B) – (C) (D)
+
+

NHMe

4. + NaNO2 + HCl   

(P), [3,–1]

P 
NHMe Me–N–N=O NHMe NHMe
NO
(A) (B) (C) (D)
NO
N=O

H-32/41 OC / R # 21-35 (Book)

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CH3

3 CrO in 2 4 (i)N H
5. 
 (P) 
  (Q) [3,–1]
(CH 3CO)2 O (ii) OH , 

    

(A) (P),    (B) (Q), o- 
(C) (Q),     (D) (P),   
6.            [3,–1]
O O
O
C–H  C–H

(A) (i) , H+ (ii) LiAlH4 (iii) H3O

+
(B) P/HI
HO OH
–
(C) (i) , H+ (ii) NH2–NH2/OH/ (iii) H3O
+
(D) Zn–Hg/HCl
HO OH
7. 
'X' 
    [4,–1]

Cl2
hv
'X'

8.     

+ (i) LiAlH4
H 3O
(i) R – C – O – R' (ii) R – C – O – C – R' (ii) H O [4,–1]
2
O O O
+
H3O + – H3O+
(iii) R – C  N (iv) R – N C

O O
(i) NaOI R' – CO3H
(v) R – C – CH3 (vi) R – C – H
(ii) H+

O
O HIO4
(vii) R – C PCC (viii)
H O

OC / R # 21-35 (Book) H-33/41

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9.      

H 2
SO 4 
         

  [4,–1]

OH CH3
(i) (ii) (iii) HO H (iv)
OH
OH CHMe2
CH2OH OH
OH
(v) H CH3 (vi) (vii)
CH2CH3
10.            [3,–1]

O
O O
CH3
(a) CH3–CH2–CHO (b) CH3–C–CH3 (c) CH3–C–H (d)
O
O O C
H
(e) CH3–C–C–OH (f) (g) HC  C–CH3 (h) CH3–CH2–OH

FILL THE ANSWER HERE

1. 2. 3. 4.
5. 6. 7.

8. 9.

10.

H-34/41 OC / R # 21-35 (Book)

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JEE (Main + Advanced)
ENTHUSIAST 2022
COURSE
ENTHUSIAST COURSE
RACE # 33 ORGANIC CHEMISTRY
M.M. : 37 TIME : 30 Min.
1.  [8, 0]

-I -II
 
Kolbes electrolysis
(A) CH3 – COOK   (P) 
NaOH  CaO
(B) CH3–COONa   (Q) 
Na
(C) CH3–Cl 
dry ether
 (R) 

Ph
(D) H / Δ

 (S) 
OH


(T) CO2
2. :  
: C–H 
C–D  [3, –1]
(A)     
(B)   
(C) 
(D)  

Cl CH2OH
+
Cl2 / Fe CH3–CO–Cl CH2OH (i) Mg(D.E) H3 O
3. X Y + Z (ii) CO (xs) W P , P  [3, –1]
+ AlCl3 H 2

CO2 H CO2H COCH3

COCH3 COCH3
(A) (B) (C) (D)
HO2C CO2H
CO2H CO2H

4. (i) 
+ Na  A + H2 [3, –1]
(ii) 2A + FeCl2  B + 2NaCl. B 

+
– – Na
2+
(A) (B) Fe (C) (D)
–

OC / R # 21-35 (Book) H-35/41

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5. 
HCl 
      
(A) o-
p-
(B) o 
p 
(C) o 
p 
(D) o 
m- [3, –1]
6.      [4, –1]
(A) 
> 
> 
> 
> 
(B) p-> p-> 
> 
(C) > 
> 
> 
(D) p-
> p-
> 2-
4-
> 2,4-
7.  [4, –1]
CF3
CH3 CHF2 CF3
(A) , , , % 
+ + + +
N(CH3)3 CH2N(CH 3)3 CH2–CH2N(CH3)3 NMe3
(B) , , ,

% 
OEt CH2–OCH3 C–OCH3 C–OCH3
(C) , , O , O % 

(D) 
Paragraph for question nos. 8 to 10
(F) (G)
Br2 h NBS 
Monobromination

(C) + (D) + (E) (Alkene)

Major
Disproportionate
Products.
Na Et2O

NaOH (i)AgOH
(J) C–OH (A) + (B)
O (ii)Br2, CCl4,  Major Minor
(X)
Kolbe
Electrolysis Na, EtOH, liq NH3

Na, liq NH3

(K) + (L) (H)
Major Minor EtOH
FeSO4 H2O2

(I)
 [3, –1]

H-36/41 OC / R # 21-35 (Book)

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8. 
(A) G 
(B) F  3° 
(C) 
A, C, F, H, I 
(D) ( A  L) 
9.  [3, –1]
(A) X to A, B (B) H to I (C) A to C, D, E (D) X to J
10.  [3, –1]
(A)  (B) 
(C) 
(D) 

FILL THE ANSWER HERE

1. 2. 3. 4.

5. 6. 7. 8.

9. 10.

OC / R # 21-35 (Book) H-37/41

 JEE (Main + Advanced) 2022
JEE (Main + Advanced) 2022
ENTHUSIAST COURSE
ENTHUSIAST COURSE
RACE # 34 ORGANIC CHEMISTRY
M.M. : 37 TIME : 30 Min.
1. 
-I 
- II [8,0]
CH2–CH2–CO2H
(A) (P) 
CH2–CH2–CO2H
CH2–CO2H
(B) (Q) 
CH2–CO2H

O O
(C) (R) 
OH
O
(D) P4O 10 (S)       
NH2

(T) 
2. PhNHNH2 (
) 
[3,–1]

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

3. (A) C8H9Br 
AgNO3  
A   
 B C8H6O4 
B    
A  [3, –1]
Br
CH2—Br
Br
(A) (B) (C) (D)
Br CH3
4.  [3, –1]
(A)  (B) 
(C)   (D) 
5. -I  
-II  [3, –1]
O
(P) H3C H (1) +ve 
OH

(Q) (2) +ve 

NH2

(R) (3) +ve  

O
(S) H3C (4) +ve 
CH 3
H-38/41 OC / R # 21-35 (Book)
 JEE (Main + Advanced) 2022
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Code :
P Q R S
(A) 1 3 2 4
(B) 4 2 3 1
(C) 1 2 3 4
(D) 4 3 2 1
6.   
P   [4, –1]
(i) HIO4
-D-
+ P + Q + R + CH3OH
(ii) H3O
Q 
R 
(A)   
(B) NaHCO3   
(C)
HIO4  
(D) 
-1,3-
  
7.   [4, –1]

(A)  , (CHCl3 + KOH) 

NH
(B) 
Ph–NH–NH2   
(C)  
0-5ºC  (NaNO2 + HCl)   
(D)  

08  10 


8.  [3, –1]

(A) P > Q > R (B) Q > R > P (C) R > Q > P (D) R > P > Q
9.  [3, –1]
(A) QR  (B) PQ  PR 
(C) P, Q 
R, 
(D) Ph–C–NHCH3 , P 
O
10.  [3, –1]
(A) P (B) Q (C) R (D) 
FILL THE ANSWER HERE
1. 2. 3. 4.

5. 6. 7. 8.
9. 10.

OC / R # 21-35 (Book) H-39/41

 JEE (Main + Advanced) 2022
JEE (Main + Advanced)
ENTHUSIAST 2022
COURSE
ENTHUSIAST COURSE
RACE # 35 ORGANIC CHEMISTRY
M.M. : 39 TIME : 30 Min.

1. 
-I         
- II [8, 0]

(i) Hg(OAc) 2 / H 2O
(A) CH2 =C–CH2–CH2–CH3 – (P) 
(ii) NaBH4 / OH
Et
CH 3 –
(i) B2H6 (THF), (ii) H2O2 + OH
(B) CH2=C–CH (iii) KMnO4
(Q) 
Et CH3

(C) CH2=C–CH2 –CH2–CH3 Reductive

Ozonolysis
(R) 
3-
KMnO4
Et 

CH3
(D) CH2=C–CH Reductive (S)  
2-
-3-
KMnO4
Ozonolysis
Et CH3

(T) 
NaHCO3 
CO2 


2. [3, –1]

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

3.    

[3, –1] 

(A) BuLi (B) LiAlH4 (C) HNO3 (D) AlCl3

4.    [3, –1]

(A)  (B)  (C) 

(D) 

5. 
H-   [3, –1]

(A)  (B)  (C) 

6,6 (D) 

6.  [4, –1]

(A) 
-S (B) 
-6,6 (C)  (D) 
-6

7.     [3, –1]

(A)  (B) 

(C) 
(D) 

H-40/41 OC / R # 21-35 (Book)

 JEE (Main + Advanced) 2022
ENTHUSIAST COURSE

8.  [4, 0]
+
H3 O
(a) + CO + HCl + AlCl3 (b) + HCN + HCl + ZnCl2
(anhydrous)

CH3 CH3

Chromic (i) SeO2

(c) Anhydride (d) (ii) MnO2

CH3

(i) Cl2 / hv (2 eq.)

(e) (ii) steam

9. 
[4, 0]
O O O OH
(i) CH3–C–CH3 (ii) CH3–C–H (iii) (iv)
O O

(v) (vi) CH3–CH2–OH

O
10.  [4, 0]
(i)  (ii)  (iii)  (iv) 
(v) 
-66 (vi)  (vii) 
-6

FILL THE ANSWER HERE

1. 2. 3. 4.

5. 6. 7.

8. 9.

10.

OC / R # 21-35 (Book) H-41/41