ORGANIC CHEMISTRY

TARGET
DPP
DAILY PRACTICE PROBLEMS
Topic – Tautomerism JEE/NEET

‘Only One Option Correct’ Type Of Questions

Direction :Each question has four choices (a), (b), (c) and (d), out of which ONLY ONE option
is correct.

1. Which of the following can show tautomerism ?

(A) (B)

(C) (D) all of these

2. Which of the following can show tautomerism?

(A) (B)

(C) (D)

3. Which of the following can show Tautomerism ?

(A) (CH3)3 CNO (B) (CH3)2NH (C) R3CNO2 (D) RCH2NO2
4. Which will not show Tautomerism ?
(A) CH3CH2CH2CH2NO2 (B) (CH3)2CH–CH2NO2
(C) CH3CH–CH2CH3 (D) (CH3)3 C–NO2
|
NO

5. Which will not show tautomerism ?

(A) (B)

(C) (D)

6. Which of the following compound show tautomerism?

(A) (H3C)2CCl–CH=CH2 (B)

(C) (H3C)2C(NO2)–CH=CH–CHO (D) None of these

7. Tautomerism will be exhibited by :

(A) (CH3)2NH (B) (CH3)3CNO (C) R3CNO2 (D) RCH2NO2

8. Which of the following will not show tautomerism ?

(A) (B)

(C) (D)

9. Which of the following is not an example of tautomeric equilibrium ?

⊕ ⊝
(A) = − = ⇌ − = −
| |
H H
(B) − = − ⇌ − =
(C) > − = ⇌> = −
 (D) – − = ⇌− = −
| |

10. I. II. III.

Among these compounds which of following is the correct order of % enol content.
(A) I > II > III (B) III > II > I (C) II > III > I (D) I > III > II

11. Which of the following compound have higher enol content.

I. II.
(A) I (B) II (C) I = II (D) none of these

12. Which of the following compound have less enol content ?

(A) I (B) II (C) both (A) & (B) (D) none of these

13. Nitroethane can exhibit one of the following kind of isomerism :

(A) Metamerism (B) Optical activity
(C) Tautomerism (D) Position isomerism

14. Which among the following compounds will show tautomerism ?

(A) 2, 2-dimethyl propanal (B) 2, 2-dimethyl-1-nitropropane
(C) Acetyl acetone (D) Benzophenone

15. For which one of the following does the position of equilibrium lie to the left ?

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

16. Correct order of enolization is :

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

17. Which of the following can show tautomerism ?

(A) (B)

(C) (D) All

18. Which of the following compound have higher enol content?

I. II.
(A) II (B) I (C) I = II (D) none of these

19. Identify the compound that exhibits tautomerism.

(A) 2-Butene (B) Lactic acid (C) 2-Pentanone (D) Phenol

O
OH
* base
20. (A),
* = 14)
(C
unknown compound (A) is -
 O OH
O O
(A) * (B) *

OH OH
OH
(C) * (D) *
*

21. Which of the following compound does not undergo base-catalyzed exchange in H2O
even through it has an -hydrogen -
O
O

(A) (B)
O

(C) (D) both 2 and 3

O
22. Identify most stable enol form of terric acid
O
O
O
H
O CH 3

OH O
O O
(A) O (B) O
CH3 CH3
O OH
O O
OH O
(C) O (D) O
CH3 CH3
O OH

23. Tautomerism is not shown by -

(A) O O (B) CH NOH
 O
(C) O (D) O
O

24. Which of the following compounds can exhibit tautomerism?

CHO COCH3
(A) (B)

CHO CH3
(C) (D) CH3 C CH3
CH3

25. Keto-enol tautomerism is observed in -

O O
|| ||
(A) C6H5 – C – H (B) C6H5 – C – CH3

O O CH3
|| || |
(C) C6H5 – C – C6H5 (D) C6H5 – C – C – C6H5
|
CH3
26. The enolic form of acetone contains -
(A) 9  bonds, 1 bond and 2 lone pairs (B) 8  bonds, 2  bonds and 2 lone pairs
(C) 10  bonds, 1  bond and 1 lone pair (D) 9  bonds, 2  bonds and 1 lone pair

27. Which statement is incorrect about the following reaction ?

| ⊝/ ( )
− − − − ℎ ⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯
||
( +) O
(A) It undergoes racemisation
(B) It undergoes D-exchange at asymmetric C* atom
(C) Rate of racemisation is equal to rate of D-exchange
(D) The product is laevorotatory

‘More than One Options Correct’ Type Of Questions

Direction :Each question has four choices (a), (b), (c) and (d), out of which MORE THAN
ONE are correct.

28. Which can show Tautomerism?

O O
O
(A) (B)

OH OH
OH O
(C) (D)

29. Keto-enol tautomerism is observed in -

O O

(A) C6H5 C H (B) C6H5 C CH3

O O O
(C) C6H5 C C6H5 (D) C6H5 C CH2 C CH3

30. Which will show tautomerism -

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

31. In which of the following keto form is more dominating than enol form -
O

(A) (B)
O O

O
O

(C) (D)
O
O

32. Which can show tautomerism

 O O O O

(A) (B)

O O O O

(C) (D)

33. Tautomerism is exhibited by :

(A) (B)

(C) (D)

34. The correct statements(s) concerning the structures E,F and G is (are) :

(E) (F) (G)

(A) E,F, and G are resonating structures (B) E, F and E, G are tautomers
(C) F and G are geometrical isomers (D) F and G are diastereomers

‘Assertion-Reasoning’ Type Of Questions

Direction :Each question has 5 choices (A), (B), (C), (D) and (E) out of which ONLY ONE
is correct.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for
Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation
for Statement-1.
(C) Statement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.
(E) Statement-1 and Statement-2 both are False.
35. Statement-1 : Compound x tautomerises to enol form but Y does not
 (X) (Y)
Statement-2 : At bridgehead carbon bond cannot exist, due to geometrical reasons.

36. Statement-1 : The enol content of cyclopentan-1,2-dione is much higher than

butanedione.

Statement-2 : Enol form is stablised by intramolecular hydrogen bonding

and delocalisation due to which repulsion among > C = O group decreases.

37. Statement-1 : Metamers can also be chain or position isomers.

Statement-2 :The term tautomerism was introduced to explain the reactivity of a
substance according to two possible structures.

38. Statement-1 : C2H5O2N shows functional isomerims as well as tautomerism

Statement-2 : Nitroethane shows tautomerism due to presence of a-hydrogens and
functional isomerism with ethyl nitrite.

39. Statement-1 : Both ethyl acetoacetate and acetylacetone exhibit keto-enol tautomerism
but the mount of enolic form is much higher in acetylacetone than in acetoacetic ester.
Statement-2 : Keto group is a much better electron withdrawing group than an ester
group.

40. Statement-1 : Ethyl acetoacetate gives reddish violet colour on treatment with ferric
chloride.
Statement-2 : It exists predominantly in the keto-form

‘Compression’ Type Of Questions

#
Migration of acidic hydrogen from -carbon to electronegative atom which is bonded
with multiple bond is the cause of tautomers
 H O O H
R C C R R C C R
R R
The conversion of keto form in to an enol form is called enolisation which depends on
various factors like structural factor, temperature and nature of solvent.In general cases
the equilibrium lies well to the left. In certain cases, however, a larger amount of the enol
form is present.Enolic form predominates in -diketones, in molecules in which the
enolic double bond is m-conjugation with another double bond, in molecules that contain
two or three bulky aryl groups and highly fluroinated enols.

41. Which one of the following has max enol content -

(A) 2,3-heptanedione (B) 2,4-heptanedione
(C) 2,5-heptane dione (D) 2,6-heptanedione

42. Correct order of ease of enolisation is -

O O O O O O

(A) < < (B) < <

O O O O O O

(C) < < (D) < <

43. Which of the following shows maximum enol content -

O O
(A) CH3 C CH3 (B) Cl2CH C CH3
O O
(C) CF3 C CHF2 (D) CH3 C H

44. Following compounds show tautomerism except -

O CH3 O
(A) CH3 C CH3 CH3 (B) CH3 C C CH3
CH3
O O O
(C) CH3 C OH (D) CH3 C CH2 C OC2H5
 ANSWER KEY

1. D 2. D 3. D 4. D 5. D 6. A 7. D 8. C 9. A 10. B

11. A 12. B 13. C 14. C 15. A 16. A 17. D 18. B 19. C 20. B

21. D 22. C 23. A 24. B 25. B 26. A 27. D 28. A,D 29. B,D

30. A,B,D 31. A,B,C 32. A,B,C 33. A,C,D 34. B,C,D 35. A 36. A 37. D

38. A 39. A 40. A 41. B 42. A 43. C 44. C