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BHUBANESWAR CENTRE

TOPIC:(STRUCTURAL ISOMERISM_TAUTOMERISM) RACE # 3

1. Tautomerism is not exhibited by :-

(1) CH=CH–OH (2) O (3) O (4) O O

O O
2. Which have most stable enol form :-
(1) CH3–C–CH2–C–CH3 (2) CH3–C–CH2–C–O–CH3
O O O O

O
(3) CH3–C–CH3 (4)
O
3. Which of the following compound will undergo tautomerism ?
O

O O O O

(1) (2) (3) C–H (4) CH3

O
4. Keto –enol tautomerism is observed in -
O O O
(1) H5C6 – C – H (2) H5C6 – C – CH3 (3) H5C6 – C – C 6H5 (4) All of these
5. Which of following compounds forms highly unstable enol ?

O
O O
(1) (2) (3) O (4)
O

6. Keto and enol forms of a compound are related to each other as :

(1) resonance structures (2) conformations
(3) configurational isomers (4) constitutional isomers
7. The order of stability of the following tautomeric compound is :-

OH O O O OH O
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CH2=C–CH2–C–CH3 CH3–C–CH2–C–CH3 CH3–C=CH–C–CH3
I II III
(1) I > II > III (2) III > II > I (3) II > I > III (4) II > III > I
8. Which of the following cannot show tautomerism :-

(1) Acetone (2) CH2 = CH—OH (3) (4)

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9. Which of the following compound has highest enol content ?
O O O O O O O O
(1) (2) Ph (3) Ph Ph (4)
10. Percentage enol content maximum in :-

O
(1) (2) O (3) (4)
O O
O O O O
11. The keto isomer of the following compound is :-
OH
HO OH

HO OH

OH
O O O OH
O O O OH HO OH O OH

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

O O HO OH O O HO O
O OH OH O
12. The most stable enolic form of 2, 4–pentanedione is :-
OH O OH O
(1) CH2=CH–CH2–C–CH 3 (2) CH3–C=CH–C–CH3
(3) CH2=CH–CH=CH 2 (4) CH3–C=C=C–CH 3
OH OH OH OH
13. Order of enol contents of the following compound is :-
O
O
O

(I) (II) (III)

(1) I > II > III (2) I > III > II (3) II > I > III (4) III > II > I
14. Which of the following compound do not show tautomerism :-
O
Ar
(1) CHCHO (2) (3) (4) O
Ar
O

15. How many of following compounds are showing tautomerism phenomenon :-

O O O O
CH3 CH3
, , ,
CH3 CH3
N–O–H
(1) One (2) Two (3) Three (4) Four

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BHUBANESWAR CENTRE

TOPIC:(STRUCTURAL ISOMERISM_TAUTOMERISM) RACE # 3

ANSWER KEY
Qns 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15
Ans 4 1 4 2 2 4 2 4 3 3 3 2 2 3 2

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