DPP NO.

(JEE MAIN+ADVANCED)
Max Marks: Max Time:

For the below compounds, mention the number of replaceable

]
Hydrogen by deuterium DO–/D2O (prolonged treatment) :

TB
O

[II
NA
(a)
O
RA

(b)
IN

(c) O
CH

(d) O
SA

Page No. 1
 O

(e) O
O

(f) O
O

]
TB
(g) H3C CH2 C CH CH CH3
O

(h) HO O [II
A
O

(i) Ph C NH CH3
N
RA

HO CH3

(j)
OH
IN
CH

(k) CH3
SA

(l) O

Page No. 2
 ANSWERS

(a) 4
(b) 3
(c) 4
(d) 4
(e) 6
(f) 5
(g) 6
(h) 6

]
(i) 1

TB
(j) 3
(k) 4
(l) 2

[II
AN
RA
IN
CH
SA

Page No. 3
 H

C OH

8. Yes (shows G.I.)

9. No –
10. No –
OH O

11. Yes Ph OEt (shows G.I.)

]
TB
[II
AN
RA
IN
CH
SA

Page No. 4
 DPP NO. (JEE MAIN+ADVANCED)
Max Marks: Max Time:

1. What statement is correct for Keto-enol tautomerism ?

]
(A) Tautomerism is catalysed by acid and base

TB
(B) Tautomers are present in dynamic equilibrium state
(C) Generally keto form is more stable than enol form
(D) All

2. Tautomerism form of this compound is/are :

O O [II
A
C
H
N
RA

H H
O O O O
IN

H H

(A) (B)
CH

H
O O
SA

(C) (D)All of these

Page No. 1
3. Tautomer in following is/are triad system :
O

(A)CH3 COCH3 (B)CH3 CH2 NO2 (C) (D)HCN

4. In each of the following pairs which is more stable :

H

O O O O

]
C C C C

TB
(a) H3C CH2 CH3 H3C CH CH3

(I) (II)

[II
H

O O O O
A
(b)
N
(I) (II)
RA

O O
H

C CH3 C O
IN

H3C C H3C C

(c) O CH2

(I) (II)
CH
SA

Page No. 2
 OH
O

OH
(d) O

(I) (II)

O CH3
H

]
C CH2

TB
CH3 O O C
H3C CH2
C
C CH2
CH
(e) O H3C

(I)

[II
5. In each of the following sets of compounds write the decreasing
(II)
A
order of % enol content.
O
N
RA

(a) O O

(I) (II) (III)

IN
CH

(b) O O O O

(I) (II) (III) (IV)

SA

Page No. 3
 O O O O
O

(c) N

(I) (II) (III) (IV)

O
O O O

C
C C C
6. H3C CH3 D3 C CD3 H3C CH2 CH3
(I) (II) (III)

]
Among these give ease of enolization.

TB
7. How many H(Hydrogens) will be replaced by D (Deuterium) in given
compound when it is kept in mild basic medium for a long time.

O
[II
A
Deuterium exchanged product
N
8. In each of the following pairs which will have higher enol content :
O
RA

COO Et
H2C C

(a) COO Et and H3C CH3

O O
IN

COO Et
H2C C C

(b) COO Et and H3C CH2 OCH3

CH

O O O O

C C C C
SA

(c) H3C CH2 CH3

and H3C CH2 OCH3

Page No. 4
 O O O O

C C C C

(d) H3C CH2 CH3 and Ph CH2 Ph

9.
Number of deuterium (D) present in final product obtained on
prolong treatment with NaOD/D2 O

]
(A) 6 (B) 9 (C) 10 (D) 5

TB
10. The compound which will show tautomerism
OH O OH

(A) (B) O [II

(C) HO (D)None
A
11. The tautomerism having Keq more than 1.0
N
O OH

O O
RA

(A)
OH O O O
IN

(B)
O OH
CH

O O

(C)
SA

Page No. 5
 O OH

C
H2C CH3
(D) H3C CH3

12. Compound having maximum enol content among following.

O O O
O
O O

]
O

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

[II
N A
RA
IN
CH
SA

Page No. 6