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Chapter Name
Isomerism

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Isomerism

1. Which of the following is a pair of metamers ?

(1) (2)

(3) (4)

2. The correct relationship among the following pairs of given compounds is

(I,II) (II,III)

(1) Functional Isomers Metamers

(2) Metamers Functional Isomers

(3) Metamers Metamers

(4) Functional Isomers Functional Isomers

3. Which of the given set of molecules have similar molecular formula :

(1) Nonane,2-methylheptane (2) 3-Isopropylcyclopent-1-ene, 3-methylhexane
(3) 3-Methylcyclopent-1-ene,penta-1,3-diene (4) Ethylcyclohexane, oct-2-ene

4. Which of the following pairs of compounds are chain isomers.

(1) Isobutyl alcohol and s-pentyl alcohol (2) Isobutyl alcohol and t-butyl alcohol
(3) Secpentyl alcohol and neopentyl alcohol (4) Ethyl alcohol and ethylene glycol

5. A position isomer of 2-pentanone is :

(1) 3-Pentanone (2) 3-Methyl-2-butanone
(3) 1-Pentanal (4) 2,2-Dimethylpropanal
6. o–Cresol & benzyl alcohol are :
(1) Functional isomers (2) Position isomers (3) Chain isomers (4) All the above
7. Monocarboxylic acids are functional isomers of :
(1) Alcohols (2) Ethers (3) Esters (4) Aldehydes and ketones.
8. CH3CONH2 & HCONHCH3 are called :
(1) Position isomers (2) Chain isomers (3) Tautomers (4) Functional isomers
9. Which of the following pair of compounds are not isomers ?
(1) Propyne and cyclopropene (2) Propyne and propadiene
(3) Propene and cyclopropene (4) 1–Propanol and methyoxyethane

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10. Saturated acyclic ethers are isomeric with :

(1) Aldehydes (2) Ketones

(3) Both aldehydes and ketones (4) Alcohols

11. Degree of unsaturation in is :

(1) 3 (2) 4 (3) 7 (4) 6.

12. How many positional isomers are possible for dimethylcyclohexane ?

(1) 3 (2) 4 (3) 5 (4) 6

13. How many aromatic isomers are possible for trichlorobenzene (C6H3Cl3) ?
(1) 2 (2) 3 (3) 4 (4) 5

14. The number of ether isomers represented by formula C4H10O is (only structural) :
(1) 4 (2) 3 (3) 2 (4) 1

15. Total number of 2° amine isomers of C4H11N would be (only structural) :

(1) 4 (2) 3 (3) 5 (4) 2

16. Which of the following compounds will not show geometrical isomerism ?

(1) Azomethane (2) 1-Bromo-2-chloroethene

(3) 1-Phenylpropene (4) 2-Methyl-2-butene
17. Which of the following compound can not show geometrical isomerism ?

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

18. Which of the following will not show geometrical isomerism ?

(1) CH3 – N  N – CH = CH2 (2)

(3) CH3 – CH = N – OH (4) Cl–CH=C=CH–Cl
19. Among the given compounds identify the pair of geometrical isomers :-

(1) I & II (2) I & III (3) II & IV (4) III & IV

20. Geometrical isomerism is shown by :

H CH3 l CH3 CH 3 CH3 Br CH3
(1) (2) CH C = C H (3) C=C (4)
H
C=C
H 3 CH 3 H Br C = C H

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21. Which of the following compound does not have geometrical isomers ?
(1) 2-Pentenoic acid (2) 2-Butenoic acid (3) 3-Pentenoic acid (4) 3-Butenoic acid
22. Which of the following compound can show geometrical isomerism ?

(1) (2)

(3) (4)

23. How many geometrical isomers are possible for the given compound ?

(1) 2 (2) 4 (3) 6 (4) 8

24. Total number of geometrical isomers in the given compound is :

C = CH – DC = CD – HC = C

(1) 2 (2) 4 (3) 6 (4) 8

25. Total number of geometrical isomers in the given compound is :

(1) 3 (2) 6 (3) 8 (4) 16

26. No. of Geometrical isomers for following compound is :

(1) 8 (2) 16 (3) 32 (4) 10

27. Which of the following will form only one oxime on reaction with NH2OH solution ?

28. Select the correct options for molecular formula C2H2Cl2 :

(1) The total number of isomers is 4.
(2) All the structures show geometrical isomerism.
(3) All isomers have 5 bonds and one  bond.
(4) Its has linear shape.

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29. Identify (Z) - 2 - pentene :-

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

30. The 'E'-isomer is/are :

(a) (b)

(c) (d)

(1) only (a) (2) only (b) (3) (a) and (b) (4) All

31. The correct stereochemical formula of Trans-3-chloro-1-phenylbut-1-ene is :

(1) (2)

(3) (4)

32. Which of the following is a syn isomer :

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

33. Which of the following is not true for maleic acid and fumaric acid ?
(1) Configurational isomers (2) Stereo isomers
(3) Z and E isomers (4) Constitutional isomers

34. The incorrect order with respect to the properties mentioned for the following pair of compounds is :

(a) < (Stability)

(b) < (Stability)

(c) > (Boiling point)

(d) > dipole moment ()

(1) (b), (c) and (d) (2) (b) and (c) (3) (a) and (d) (4) (c) and (d)

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35. The correct order/s for the given pair of isomers is

(1) > (Melting point)

(2) < (Dipole moment)

(3) > (Boiling point)

(4) > (Water solubility)

36. Number of chiral carbon atoms in the compound w, x, y and z respectively would be :

(1) 3, 0, 2, 1 (2) 2, 1, 0, 1 (3) 3, 1, 2, 1 (4) 1, 1, 2, 0

37. Which of the following compounds possesses a chiral centre ?

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

38. will shows :

(1) Geometrical isomerism only (2) Optical isomerism only

(3) Geometrical and optical isomerism (4) Neither geometrical nor optical isomerism

CH3 H
39. The structure shows C=C H
CH3 C — COOH

CH3
(1) Geometrical isomerism (2) Optical isomerism
(3) Geometrical & optical isomerism (4) none

40. Which of the following compounds exhibits stereoisomerism ?

(1) 2-methylbutene-1 (2) 3-methylbutyne-1
(3) 3-methylbutanoic acid (4) 2-methylbutanoic acid
41. Which of the following is an optically active compound ?
(1) 1–Butanol (2) 1–Propanol
(3) 2–Chlorobutane (4) 4–Hydroxyheptane

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42. Meso form of tartaric acid is :
(1) Dextorotatory
(2) laevorotatory
(3) neither Laevo not dextro rotatory due to internal compensation
(4) A mixture of equal quantities of dextro and leavorotatory forms

43. The following two compounds are :

and

(1) Enantiomers (2) Diastereomers (3) Identical (4) Epimers

44. Stereo isomers which are not mirror image of each other, are called : -

(1) Enantiomers (2) Tautomers (3) Metamers (4) Diastereomers

45. Which of the following amine is optically active ?

(1) CH3NH2 (2) CH3NHCH3

(3) CH3CH2CH2– (4) sec-Butylamine

46. Which of the following compound has ‘S’ configuration ?

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

47. The correct configuration assigned for given compound :

(1) 2R, 3R (2) 2S, 3S (3) 2R, 3S (4) 2S, 3R

48. Which of the following compound has 'D' configuration ?

(1) (2)

(3) (4)

49. represents the Fischer projection formula :

(1) D (2) L (3) d (4) 

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50. The correct IUPAC name of D-Glucose is :

(D-Glucose)

(1) (2D, 3D, 4L, 5D) 2, 3, 4, 5, 6-pentahydroxyhexanal

(2) D-2, 3, 4, 5, 6-pentahydroxyhexanal
(3) 6-oxo-(2D, 3L, 4D, 5D) - 2, 3, 4, 5, 6-pentahydroxohexane
(4) (2D, 3L, 4D, 5D) - 2, 3, 4, 5, 6-pentahydroxyhexanal

51. Consider the following organic compound :

To make it a chiral compound, the attack should be on carbon atom no.

(1) 1 (2) 3 (3) 4 (4) 7

52. Which of the following pairs of structures represent enantiomers ?

(1) and (2) and

(3) and (4) and

53. Which one among the following is not diastereomeric pair ?

(1) I and III (2) I and II (3) II and III (4) I and IV

54. How many stereoisomers (geometrical and optical) are possible for the following compound ?
CH3CH=CHCH2CH(OH)COOH
(1) 1 (2) 2 (3) 3 (4) 4

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55. Find relation between these two compounds A and B :

CH3 COOH
H OH H OH

HO H CH3 OH

COOH H

(A) (B)

(1) Enantiomer (2) Diasteromer (3) Meso (4) Identical

56. The two structures I & II represents :

(I) (II)

(1) Conformational isomers (2) Stereoisomers

(3) Constitutional isomers (4) Identical

57. In the complete rotation of butane from 0º to 360º the gauche (straggered) conformation appears
(1) once (2) Twice (3) Thrice (4) Four times

58. Which of the following is associated with Torsional strain ?

(1) Repulsion between bond pair of electrons (2) Inductive effect
(3) Bond angle strain (4) Attraction of opposite charges
59. In the given conformation C2 is rotated about C2–C3 bond anticlockwise by an angle of 120° then the conformation
obtained is :
CH3
H H

H H
CH3
(1) Fully eclipsed conformation
(2) Partially eclipsed conformation
(3) Gauche conformation
(4) Staggered conformation

60. The pair of structures given below represent

(1) Enantiomers (2) Diastereomers

(3) Structural isomers (4) conformational isomers

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61. In the following structures, which two forms are staggered conformation of ethane ?

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

62. The most stable conformation of ethylene glycol is.

(1) Anti (2) Gauche (3) Partially eclipsed (4) Fully eclipsed

63. The correct order of stability of various conformers of 2-fluoroethanol is –

(1) Anti > Gauche > Fully eclipsed > Partially eclipsed
(2) Gauche > Anti > Partially eclipsed > Fully eclipsed
(3) Anti > Partially eclipsed > Fully eclipsed > Gauche
(4) Fully eclipsed > Partially eclipsed > Gauche > Anti

64. Incorrect about the compounds I, II, III is :

, ,

(1) I & II are diastereomers (2) I & III are identical

(3) I| & III are diastereomers (4) I & II are optically active

65. Which of the following shows cis-trans isomerism ?

(1) 2-Butyne (2) 2-Butene (3) 2-Butanol (4) 2-Chloro-1-butene

66. Which can not show geometrical isomerism ?

(1) H2N2 (2) 1-Chloro-2-phenylethene

H3C
(3) C = N–OH (4) HO–N = N–OH
H3C

67. The lowest molecular weight alkane, which is optically active ?

(1) 3-methylhexane (2) 2, 3-dimethylbutane (3) 2, 3, 3-trimethylbutane (4) 2-methylhexane

68. The two compounds given below are :

(1) Enantiomer (2) Identical (3) Meso compound (4) Diastereomers

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69. Total number of stereoisomers of compound is :
CH3  CH  CH  CH3
| |
OH Br
(1) 2 (2) 4 (3) 6 (4) 8

70. CH3 – CH – CH – CH – CH3 Total number of stereoisomers in above compound is :

| | |
Br Br Br
(1) 6 (2) 4 (3) 8 (4) 16

71. CH3 – CH – CH – CH – CH3

| | |
Cl Br OH
Total number of stereoisomers in above compound is :

(1) 6 (2) 4 (3) 8 (4) 16

72. The absolute configuration of the following compound is :

(1) 2 S, 3 R (2) 2 S, 3 S (3) 2 R, 3 S (4) 2 R, 3 R

73. and are

(1) enantiomers (2) diastereomers (3) identical (4) none of these

74. How many meso steroisomers are possible for 2, 3, 4–pentanetriol :

(1) 1 (2) 2 (3) 3 (4) None

75. The total number of isomers for C4H8 is

(1) 5 (2) 6 (3) 7 (4) 8

76. The total number of isomeric alcohols with the molecular formula C4H9OH is

(1) 2 (2) 3 (3) 4 (4) 5

77. The number of possible open chain (acyclic) isomeric compounds for molecular formula C5H10 would be

(1) 8 (2) 7 (3) 6 (4) 5

78. If optical rotation produced by is + 36º then that produced by is

(1) –36º (2) 0º (3) +36º (4) unpredictable

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79. The number of optically active stereoisomers possible for butane – 2, 3 – diol :

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

80. Which of the following pair of isomers can not be separated by fractional crystallisation or distillation -

(1) Maleic acid and Fumaric acid

(2) (+)-Tartaric acid and meso - tartaric acid
(3) CH3  CH  COOH and H2N  CH2  CH2  COOH
|
NH2
(4) (+)-lactic acid and (–)-lactic acid

81. The Baeyer’s angle strain is expected to be maximum in

(1) Cyclodecane (2) Cyclopentane (3) Cyclobutane (4) Cyclopropane

82. The most stable conformation of 3-fluorobutan-2-ol is :

(1) Fully eclipsed form (2) Partially eclipsed form
(3) Gauche form (4) Anti form .

83. Which of the following is an achiral molecule?

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

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ANSWERKEY

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

5. (1) 6. (1) 7. (3) 8. (4)
9. (3) 10. (4) 11. (3) 12. (2)
13. (2) 14. (2) 15. (2) 16. (4)
17. (1) 18. (4) 19. (3) 20. (2)
21. (4) 22. (4) 23. (2) 24. (2)
25. (2) 26. (2) 27. (2) 28. (3)
29. (1) 30. (3) 31. (4) 32. (3)
33. (4) 34. (4) 35. (4) 36. (1)
37. (1) 38. (3) 39. (2) 40. (4)
41. (3) 42. (1) 43. (1) 44. (4)
45. (4) 46. (3) 47. (4) 48. (3)
49. (1) 50. (4) 51. (2) 52. (2)
53. (1) 54. (4) 55. (4) 56. (3)
57. (2) 58. (1) 59. (3) 60. (3)
61. (3) 62. (2) 63. (2) 64. (4)
65. (2) 66. (3) 67. (1) 68. (1)
69. (2) 70. (2) 71. (3) 72. (2)
73. (2) 74. (2) 75. (2) 76. (4)
77. (3) 78. (2) 79. (2) 80. (4)
81. (4) 82. (3) 83. (1)

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