Stereoisomerism

ANSWER KEY
EXERCISE-1
PART-1
1. Restricted rotation present in all the options but geometircal isomersim shown by ii, iii, iv, vii.
2. Essential conditions for geometrical isomerism are
(1) Restricted rotation must present.
(2) Two different groups must be present on both the atoms of restricted system.
(3) Groups responsible to show geometrical isomerism must be nearly in the same plane.
3. The bond across which atoms cannot rotate without breaking the bonds is called restricted rotation. e.g.

C=C, C=N, ring etc. (a  b, d  e)

e.g. C=C, C=N, (a  b, d  e)

4. (iii) , (iv) , (vi) , (vii) and (viii)

5. 5 (i, ii, iv, v ,vi )

6. (i) = E (ii) = E (iii) = E (iv) = Z

7. (a)

dipole moment : II > I

(b) Because of good packing of trans isomers.

(c)

8. W has 3, X has zero, Y has 2 and Z has only one chiral centres.

9. (i) =9 (ii) =8

10. (I) R (II) S (III) R (IV) (R, R)

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 Stereoisomerism
11. (I) D (II) (2D, 3D)

(III) Equivalent fischer projection is and configuration L.

12. (a) R (b) R (c) R (d) R

13. (i) Plane of symmetry and Centre of symmetry. (ii) Plane of symmetry.
(iii) Plane of symmetry. (iv) Plane of symmetry.
(v) Plane of symmetry and Centre of symmetry.
14. (i) POS present and COS, AOS absent. (ii) POS present and COS, AOS absent.
(iii) POS, AOS present and COS absent. (iv) POS, COS present and AOS present.
(v) POS present and COS,AOS absent. (vi) POS, COS and AOS absent.
15. Enantiomeric pair  (I & III)
Diastereomeric pairs  (I & II), (II & III)
16. (I) Enantiomers (II) Position isomers (III) Identical (IV) Diastereomers
17. (a) Functional isomers (b) Enantiomers (c) Geometrical isomers (d) Diastereomers
18. (i) Mixture of I, II and III give two fraction on fractional distillation.
(ii) I, II and III all are optically active
(iii) I and II are pair of enantiomers
(iv) I and III are optical diastereomer.
19. D/L represent nomenclature (relative configuration) while d/ represents direction of optical rotation.

20. Specific rotation is the number of degrees of rotation observed if a 1-dm (10-cm) tube is used and the
compound has concentration 1 gm/mL. Thus specific rotation [] is

[ ]t =
C
[] = Specific rotation ;  = observed angle of rotation (degree)
 = Pathlength (dm) ; C = concentration (gm/ml)
observed optical rotation
21. % Optical purity = optical rotation of pure enantiomer × 100

|d  | excess of one enantiomer over other

% Enantiomeric excess = × 100 = entire mixture
× 100
d

22. 4
23. i, ii, iii, iv
24. ii, iii, v, vi
25. (i) 3, (ii) 2, (iii) 2, (iv) 8
26. 3 (oct-2-ene, oct-3-ene, oct-4-ene)
27. 4
28. (I) 4 (II) 4 (III) 2

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 Stereoisomerism
29. 7
30. 6
31. Fully Eclipsed

32.

33. Possible eclipsed conformations = 4

CD3 CH3 CH3 CH3
H D F Cl

H D F Cl
F3C CCl3 CCl3 D3C CCl3 D3C CF3
H D CF3 F Cl

CH3
H H
34. antiform, it is most polar & stable.
H H
NO2

CHO intramolecular
H H-bonding
CH2CH 2CH=O H O
35. ;
OH H H
H

36. (I) (II) (III)

37. (i) (II) (iii)

(iv) (v) (vi)

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 Stereoisomerism
38-. (i) trans (ii) cis (iii) trans (iv) cis
(v) trans (vi) cis (vii) cis

39. First is more stable because of less steric repulsion between groups at equitorial position.

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

EXERCISE-2
1. (4) 2. (3) 3. (2) 4. (2) 5. (3) 6. (1) 7. (2)
8. (3) 9. (3) 10. (3) 11. (1) 12. (2) 13. (2) 14. (3)
15. (1)

EXERCISE-3
PART-1
1. (A) 2. (C) 3. (C) 4. (A)

PART-2
1. (2) 2. (3) 3. (4) 4. (4) 5. (2) 6. (4) 7. (2)
8. (2) 9. (1) 10. (3) 11. (2) 12. (3) 13. (2) 14. (4)
15. (2) 16. (1) 17. (3) 18. (4) 19. (3) 20. (4) 21. (1)
22. (3) 23. (1) 24. (4) 25. (4) 26. (3) 27. (1) 28. (4)
29. (2) 30. (1)

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