ASSIGNMENT

ORGANIC CHEMISTRY
Date : 29.07.2013 Topic : Tautomerism Batch : Umang (UP)

Single Choice Type

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) CH3 –CH2CH3 (D) (CH3)3C–NO2

5. Which will not show Tautomerism ?

(A) (B)

(C) (D)

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6. Which of the following compound show tautomerism ?

C=O
(A) (H3C)2CCl–CH=CH2 (B)
H
(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)

(B)
(C)
(D)

10. Which of the following will have highest percentage of enol content ?

O O O
|| || ||
(A) C 6 H 5  C  CH 2  C  OC 2 H 5 (B) CH 3  C  O  C 2 H 5

O O O O
|| || || ||
(C) CH 3  C  CH 2  C  OCH 3 (D) CH 3  C  CH 2  C  CH 3

11. 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

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

O O

I II

NO2 OCH3
(A) I (B) II (C) I = II (D) none of these

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

I II
N O N
| | O
H H
(A) I (B) II (C) both (A) & (B) (D) none of these

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

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

15. Which among the following compounds will show tautomerism ?

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

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

(A)

OH OH
| |
(B)

(C)

(D)

17. Which among the following compounds will give maximum enol content in solution ?
O O
|| ||
(A) C6H5– C –CH2––CH3 (B) CH3– C –CH2––CH3
O O
|| ||
(C) CH3– C –CH2–CH2–CH3 (D) CH3– C –CH2–COOC2H5

18. Correct order of enolization is :

(A) CH3COCH3 < C3COCH2COOC2H5 < COCH2COOC2H5 < CH3COCH2CHO
(B) CH3COCH2COOC2H5 < COCH2COOC2H5 < CH3COCH2CHO < CH3COCH3
(C) COCH2COOC2H5 < CH3COCH2CHO < CH3COCH3 < CH3COCH2COOC2H5
(D) CH3COCH2CHO < CH3COCH3 < CH3COCH2COOC2H5 < COCH2COOC2H5

19. Which of the following can show tautomerism ?

O
CH3
(A) O (B)
CH3

(C) (D) All

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

O O
|| ||
C C
I CH3 II CH3
OH
OH
(A) II (B) I (C) I = II (D) none of these

21. Identify the compound that exhibits tautomerism. [AIEEE 2011, 4/120]
(A) 2-Butene (B) Lactic acid (C) 2-Pentanone (D) Phenol

Multiple Choice Type

22. Tautomerism is exhibited by : [JEE-98]

(A) (B)

(C) (D)

23. The correct statements(s) concerning the structures E,F and G is (are) : [JEE-08, 4/163]

(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

DIRECTIONS :
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.

24. Statement-1 : Compound x tautomerises to enol form but Y does not

Statement-2 : At bridgehead carbon  bond cannot exist, due to geometrical reasons.

25. 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.

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26. 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.

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

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

28. Statement-1 : Both ethyl acetoacetate and acetylacetone exhibit keto-enol tautomerism but the amount
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.

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

True/ False Type

30. Resonance and tautomerism refer to one and the same phenomenon.

Column Match Type

31. Match the following :

Compound Enol percentage

O

(A) (p) 99.99

(B) CH3–CO–CH2–COOC2H5 (q) 7.5

O

(C) (r) 96

(D) C6H5 – CO – CH2 – COC6H5 (s) 1.2

Subjective Type
32. Which of the following will show tautomerism.
(a) Butanal (b) Butanone (c) Cyclohexanone (d) Ph — C — Ph
||
O

(e) D3C — C — CD3 (f) (g) CH2=CH—OH (h) HO—CH=CH—OH

||
O

33. Write tautomer of the following compounds

(i) CH3 – CH = NH (ii) (iii) CH3 – CH – NO2 (iv) CH3  C  CH2  C  CH3
|| ||
CH 3 O O

34. Monocarbonyl compounds have very small percentage enol form at equilibrium. Explain.

35. If is added to NaOH solution. Acid base reaction takes place and

snatches H from compound. Which carbon will loose H+ most easily and why ?

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 ANSWER KEY
Single Choice Type
1. (D) 2. (D) 3. (D) 4. (D) 5. (D) 6. (A) 7. (D)

8. (C) 9. (A) 10. (D) 11. (B) 12. (A) 13. (B) 14. (C)

15. (C) 16. (A) 17. (D) 18. (A) 19. (D) 20. (B) 21. (C)

Multiple Choice Type

22. (ACD) 23. (BCD)

Assertion / Reasoning Type

24. (A) 25. (A) 26. (D) 27. (A) 28. (A) 29. (A)

True/ False Type

30. False

Column Match Type

31. (A) - s ; (B) - q ; (C) - p ; (D) - r

Subjective Type
32. (a), (b), (c), (e), (g) and (h)

OH
|
33. (i) CH2 = CH – NH2 (ii) CH3  C  CH2 (iii) (iv) CH3  C  CH  C  CH3
|| |
O OH

34. Ketoform is more stable due to greater strength of the carbon-oxygen double bond as compared to the
carbon carbon double bond.

35. Q loses H+ easily because anionic charge on Q is delocalized with two > C = O group.

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