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(JEE ADVANCED - 2019)
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Assignment - XII

Chemistry : Reaction Mechanism

Write the product of following reaction : 8.


OH OH

H2SO4
1. 
 TsCl LiAlH 4

Pyridine 0º
 (A)   (B)


H
HO 9. 

H2SO4 OH OH
2. 

CH3
HCl
OH OH 10. CH2  
H 2SO4
3. Ph 
Ph 
H
11. O 

OH

12. Br2
4. OH H
 OH 
CH 2Cl2

OMe

OH 13.  HBr 

H
 (1 equivalent)
5. O

O
O
14. H O
6. H 
3



CH2OH
TsCl
7. 
Pyridine 0º
 (A) 
80º
 (B)
OH (HPMT Solvent
2 Kalrashukla Classes : JEE - Advance

15.
H
 H2SO4

25. 

OH
H
16. 
 R OH

SOCl
HBr 26.  2
Pyridine, 

17. 
CCl

4

OH
H SO , 0ºC

2 4
 A  B
18. H O 2  HCl
OH
Cl

H (excess)
 
27. 
HBr OH

R O /h
 OH
19. 2 2

CH3


CH3 H

28.
C CH2 O
20. 
A HBr

(major) O


H ROH
 (A)   (B) H 2SO4
 A
 H 29.
21. (major)
O CH OH2
(major)


22. H2 H
OH   A  B HCl
30.  P
(major)
H 2SO4
 OH
23. 

OH

O HO
H O
31. 
3

24. Conc. H 2SO 4
 
Assignment - Chemistry 3

H CH3
OH H NaOH (Alc.)


32. H
37.

 Br

HBr Conc. H 2SO4


OH   38. Ph  
33.

OH
 Ph Ph
NMe3

34. OH


A CH3 H
(major) Br
H
D Alc. KOH
OH 39.  

H
H 2SO4
35.  A

(major)
OSO2CF3
CH3
CH OH
   40.  3

36. N(CH3)3OH  X Y  (30ºC)

91% 9%

ANSWERS KEY

1. 2.
6. 7. O
O O (B)

Ph
3.
Ph
8. 9.

Ome (B)
4. OMe O
OH
O
10. 11.
O
Cl
5.
O
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OH

12. 13. 28. 29.


O Br Br
HO

OH
30. Cl
14. 15.
OH

16. 17. 31.

Br

Br
18. O 19. 32.

33. OH
Br
20. 21. OR Br
O
(B)

22. 23. 34. 35.


O
(B)

36.

CH3
O 37. H
H H
24. 25.

38. 39.
R
Cl
Ph Ph

26. 27. OMe

40.