Unit - 27

ISOMERISM AND STEREOCHEMISTRY OF ORGANIC COMPOUNDS

MULTIPLE CHOICE QUESTIONS

1. The maximum number of isomers for an alkene with the molecular formula
C4H8 is
(a) Two (b) Three (c) Four (d) Five

2. How many chain isomers could be obtained from the alkane C6H14 ?
(a) Four (b) Five (c) Six (d) Seven

3. The number of structural and configurational isomers of a bromo compound,

C5H9Br, formed by the addition of HBr to 2-pentyne respectively are
(a) 1 and 2 (b) 2 and 4 (c) 4and 2 (d) 2 and 1

4. Which of the following is an optically active compound?

(a) 1-Butanol (b) 1-Propanol
(c) 2-Chlorobutane (d) 4-Hydroxyheptane

5. Which one of the following can exhibit cis-trans isomerism?

(a) CH3-CHCl-COOH (b) H  C  C  C l
(c) C l C H  C H C l (d) C l C H 2  C H 2 C l.

6. Which of the following will have least hindered rotation about carbon-carbon
bond?
(a) Ethane (b) Ethylene (c) Acetylene (d) Hexachloroethane

7. How many chiral carbon atoms are present in 2,3,4-trichloropentane ?

(a) Three (b) Two (c) One (d) Four

8. Isomers of a substance must have the same

(a) Structural formula (b) Physical properties
(c) Chemical properties (d) Molecular formula

9. An organic molecule necessarily shows optical activity if it

(a) contains asymmetric carbon atoms
(b) is non-polar
(c) is non-superimposable on its mirror image
(d) is superimposable on its mirror image.

10. The stability of the compounds

THE GUIDANCE 58/1, Kalu Sarai, Sarvpriya Vihar, New Delhi-16, Ph: 41828089, 46043741 (1)
 (a) (iv) > (iii)>(i) >(ii) (b) (i) > (iii) > (ii) > (iv)
(c) (ii) > (iii)> (i) > (iv) (d) (iv) > (i) > (iii) > (ii)

11. An organic compound C4H8O, is found to be optically active.

Which of the following could it be ?
(a) C H 3  C O  C H 2  C H 3 (b) C H 3  C H 2  C H 2  C H O
(c)  C H 3 2 C H CHO (d) CH2  C H  C H O H   C H 3

12. One recently discovered allotrope of carbon (e.g.C60) is commonly known as

(a) Flourine (b) Fullerene (c) Flourene (d) Freon.

13. Which one of the following is the stablest structure of cyclohexatriene ?

(a) Chair form (b) Boat form (c) Half chair form (d) Planar form

14. How many structural isomers are there of C4H10O that are ethers?
(a) 1 (b) 3 (c) 2 (d) 4

15. Which organic structure among the following is not an isomer of the compound
C H 3  C O  C H 2C H 2C H 2C H 3 ?
(a) CH3CH2OCH =CHCH2CH3 (b) CH3CH=CHCH2CH2 CHO
(c) (CH3)2CH-CO-CH2CH3 (d) CH3CH2COCH2CH2CH3¬.

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

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

17. meso –Tartaric acid is optically inactive due to the presence of

(a) Molecular symmetry (b) Molecular asymmetry
(c) External compensation (d) Two asymmetric carbon atoms.

18. The process of separation of a racemic modification into-d-and l-enantiomers is

called
(a) Resolution (b) Dehydration
(c) Revolution (d) Dehydrohalogenation
THE GUIDANCE 58/1, Kalu Sarai, Sarvpriya Vihar, New Delhi-16, Ph: 41828089, 46043741 (2)
19. The most stable conformation of ethylene glycol is
(a) Anti (b) Gauche (c) Partially eclipsed (d) Fully eclipsed

20. In the reaction, C H 3 C H O  H C N  C H 3 C H  O H  C N , a chiral centre is

produced. This product would be
(a) Laevorotatory (b) Meso-compound
(c) Dextrorotatory (d) Racemic mixture

21. Which of the following has zero dipole moment ?

(a) cis -2-Butene (b)trans -2-Butene
(c) 1-Butene (d) 2-Methyl-1-propene

22. How many stereoisomers are there for tartaric acid ?

(a) 2 (b) 3 (c) 4 (d) 5

23. The total number of isomers for C4H8 is

(a) 5 (b) 6 (c) 7 (d) 8

24. The two compounds shown in the figure below are

(a) Diastereomers (b) Enantiomers

(c) Epimers (d) Regiomers

25. The number of possible enantiomeric pairs that can be produced during
monochlorination of 2-methylbutane is
(a) 2 (b) 3 (c) 4 (d) 1

26. The correct statement about the compounds A,B,C

(a) A and B are identical (b) A and B are diastereomers

(c) A and C are enantiomers (d) A and B are enantiomers
27. How many optically active stereoisomers are possible for butane-2,
3-diol ?
(a) 1 (b) 2 (c) 3 (d) 4

28. The isomers which can be converted into another form by rotation of the
THE GUIDANCE 58/1, Kalu Sarai, Sarvpriya Vihar, New Delhi-16, Ph: 41828089, 46043741 (3)
 molecule around single bond are
(a) Geometrical isomers (b) Conformers
(c) Enantiomers (d) Diastereomers

29. The most stable conformation of n-butane is

(a) skew-boat (b) Eclipsed (c) Gauche (d) Staggered-antill

30. The compound given below are

(a) Enantiomers (b) Identical

(c) Regiomers (d) Diastereomers

31. In the boat conformation of cyclohexane, the most destabilizing intereaction is

(a) Eclipsing (b) 1, 3-Diaxial
(c) 1, 3-Diequatorial (d) Flagpole-Flagpole

32. Which of the following compound is not chiral

(a) D C H 2 C H 2 C H 2 C l (b) C H 3 C H D C H 2 C l
(c) C H 3 C H C l C H 2 D (d) C H 3 C H 2 C H D C l

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

(a) Cyclodecane (b) Cyclopentane
(c) Cyclohexane (d) Cyclooctane

34. The optically active tartaric acid is named as D-(+) – tartaric acid because it has
a positive
(a) Optical rotation and is derived from D-glucose
(b) pH in organic solvent
(c) Optical rotation and is derived from D-(+)- glyceraldehyde
(d) Optical rotation only when substituted by deuterium.

35. The following two compounds are

are

(a) Enantiomers (b) Diastereomers

(c) Identical (d) Epimers.

36. Which of the following compounds will exhibit geometrical isomerism?

(a) 1-Phenyl-2-butene (b) 3-Phenyl-1-butene
(c) 2-Phenyl-1-butene (d) 1,1-Diphenyl-1-propene

THE GUIDANCE 58/1, Kalu Sarai, Sarvpriya Vihar, New Delhi-16, Ph: 41828089, 46043741 (4)
37. will show

(a) Geometrical isomerism (b) Optical isomerism

(c) Geometrical and optical isomerism
(d) Neither geometrical nor optical isomerism

38. The (R)- and (S)-enantiomers of an optically active compound differ in

(a) their reactivity with achiral reagents
(b) their optical rotation of plane polarized light
(c) their melting points
(d) their solubility in achiral reagents.

39. But-2-ene exhibits cis-trans- isomerism due to

(a) rotation around C3-C4 sigma bond
(b) restricted rotation aroundC=C bond
(c) rotation around C1-C2 bond
(d)rotation around C2-C3 double bond.

40. The pair of structures given below represent

(a) Enantiomers (b) Diastereomers

(c) Structural isomers (d) Two molecules of the same compound

41. Consider the following organic compound,

1 2 3 4 5 6 7

CH 3
CH2CH2CH2CH2CH2CH3
To make it a chiral compound, the attack should be on carbon
(a) 1 (b) 3 (c) 4 (d) 7

42. The number of ether metamers represented by the formula C4H10O is

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

43.

THE GUIDANCE 58/1, Kalu Sarai, Sarvpriya Vihar, New Delhi-16, Ph: 41828089, 46043741 (5)
 Hydrogenation of the above compound in the presence of poisoned palladium
catalyst gives
(a) optically active compound (b) an optically inactive compound
(c) a racemic mixture (d) a diastereomeric mixture

44. The number of isomers for the compound with molecular formula C2BrClFI is
(a) 3 (b) 4 (c) 5 (d) 6

45. Which of the following compounds exhibits stereoisomerism?

(a) 2-Methylbutene-1 (b) 3-Methylbutyne-1
(c) 3-Methylbutanoic acid (d) 2-Methylbutanoic acid

46. Which of the following has the lowest dipole moment ?

(a) (b) CH3—C  C — CH3

(c) CH3CH2C  CH (d) CH2 = CH—CCH

47. Which is a pair of geometrical isomers?

(a) I and II (b) I and III (c) II and IV (d) III and IV

48. A similarity between opitical and geometrical isomerism is that

(a) each forms equal number of isomers for a given compound
(b) if in a compound, one is present then so is the other.
(c) both are included in stereoisomerism
(d) they have no similarity.

49. Which of the following does not show geometrical isomerism?

(a) 1, 2-dichloro-1-pentene (b) 1, 3-dichloro-2-pentene
(c) 1, 1-dichloro-1-pentene (d) 1, 4-dichloro-2-pentene

50. The absolute configuration of the following compound is

(a) 2 S, 3 R (b) 2 S, 3 S (c) 2 R, 3 S (d) 2 R, 3 R

51. Among the following four structures I to IV

THE GUIDANCE 58/1, Kalu Sarai, Sarvpriya Vihar, New Delhi-16, Ph: 41828089, 46043741 (6)
 It is true that
(a) Only II and IV are chiral compounds
(b) All four are chiral compounds
(c) Only I and II are chiral compounds
(d) Only III is a chiral compound

52. The total number of acyclic and cyclic isomers including stereoisomers
possible for the molecular formula, C5H10 is
(a) 10 (b) 8 (c) 9 (d) 12

53. The total number of acyclic isomers including the stereoisomers (geometrical
and optical) with the molecular formula C4H7Cl is
(a) 12 (b) 11 (c) 10 (d) 9

54. Which of the following molecules can exhibit conformational isomerism?

(a) CH3OH (b) H2O2 (c) NH2-NH2 (d) All the three

55. Which of the following shows geometrical isomerism ?

(a) (b) 1,2-Dimethylcyclopropane
(c) 1, 2-Dichloroethene (d) All the three

56. The number of stereoisomers and optical isomers possible for the compound,
abd C—Cabd are respectively.
(a) 3, 3 (b) 3, 2 (c) 2, 3 (d) 2, 2

57. Enantiomers have

(a) identical m.p/b.p but different refractive indices
(b) identical m.p/b.p and refractive indices but rotate plane polarized light in
opposite directions but to the same extent
(c) different refractive indices and rotate plane polarized light in the same
direction but to different extents
(d) different m.p/b.p. but rotate plane of polarized light in different directions
but to the same extents

58. (+)- and (-) Lactic acid can be separated by using

(a) Fractional crystallization
(b) Treatment with another optically active acid
(c) Treatment with an optically active base
(d) Distillation under reduced pressure
THE GUIDANCE 58/1, Kalu Sarai, Sarvpriya Vihar, New Delhi-16, Ph: 41828089, 46043741 (7)
59. Which of the following statements is correct?
(a) The presence of chiral carbon is an essential condition for enantiomerism
(b) Functional isomerism is a kind of stereoisomerism
(c) Diastereomers are always optically active
(d) Compounds containing one chiral carbon atom are always optically active

60. Which one of the following is optically active?

(a) Glycerine (b) Acetamide
(c) Glycylalanine (d) Dimethylaniline

61. Which of the following molecules will not show optical activity?

(a) (b)

(c) (d)

62. Consider the following structures and pick up the right statement

(a) I and II have R- configuration (b) I and III have R-configuration

(c) Only III has S-configuration (d) Both (a) and (c) are correct.

63. The IUPAC name of is

(a) (Z)-4,6-Dimethyloct-4-en-3-one
(b) (E)-4,6-Dimethyloct-4-en-3-one
(c) (Z)-3,5-Dimethyloct-4-en-6-one
(d) (E)-3,5-Dimethyloct-4-en-6-one

64. The IUPAC name (including the stereochemical notation for the chiral carbon)

of is

(a) (S)-2-Bromo-(Z)-hex-3-en-4-one (b) (R)-2-Bromo-(E)-hex-3-en-4-one

THE GUIDANCE 58/1, Kalu Sarai, Sarvpriya Vihar, New Delhi-16, Ph: 41828089, 46043741 (8)
 (c) (R)-5-Bromo-(Z)-hex-3-en-2-one (d) (S)-5-Bromo-(E)-hex-3-en-2-one

65. The R-isomer among the following are:

(a) (i) and (ii) (b) (i) and (iii) (c) (ii) and (iii) (d) (iii) and (iv)

66. Select the S-isomer form the following

67. Erythro isomer among the following is

THE GUIDANCE 58/1, Kalu Sarai, Sarvpriya Vihar, New Delhi-16, Ph: 41828089, 46043741 (9)
 Unit - 27
ISOMERISM AND STEREOCHEMISTRY OF ORGANIC COMPOUNDS
Answer Key
Q.No. Ans. Q.No. Ans. Q.No. Ans. Q.No. Ans. Q.No. Ans.
1. c 15. b 29. d 43. b 57. b
2. b 16. c 30. b 44. d 58. c
3. b 17 a 31. a 45. d 59. d
4. c 18. a 32. a 46. b 60. c
5. c 19. b 33. a 47. c 61. c
6. a 20. d 34. c 48. c 62. a
7. a 21. b 35. a 49. c 63. a
8. d 22. b 36. a 50. b 64. d
9. c 23. b 37. c 51. c 65. a
10. a 24. b 38. b 52. d 66. c
11. d 25. a 39. b 53. a 67. d
12. b 26. d 40. c 54. d
13. d 27. b 41. b 55. d
14. b 28. b 42. b 56. b

SOLUTIONS

1. Four alkenes:
(i) C H 3C H 2C H CH2 1  b u t e n e  , (ii) (cis -2-Butene)

(iii) t(rans -2-Butene)

(iv) (2-Methylpropene).

2. Five chain isomers-Refer to review of fundamentals.

THE GUIDANCE 58/1, Kalu Sarai, Sarvpriya Vihar, New Delhi-16, Ph: 41828089, 46043741 (10)
3. Addition of HBr to 2-pentyne gives two structural isomers (I) and (II)
C H 3  C  C  C H 2 C H 3   C H 3 C  B r   C H C H 2 C H 3 (I )
HBr


 C B r  C H 2C H 3 II 
C H 3C H
Each one of these will exist as a pair of geometrical isomers.
Thus, there are two structural and four configurational isomers

4. 2-chlorobutane contains a chiral carbon and hence is optically active

5. CICH=CHCl.

6. Because of the bigger size of Cl than H, the rotation about carbon-carbon single
bond in hexa chloroethane is more hindered than, in ethane on the other hand
because of the presence of double bond in ethylene, and triple bond in
acetylene, the rotation about carbon-carbon bond is highly hindered, Thus
ethane has the least hindered rotation.

7.

has in all three chiral carbon atoms; the middle one is a pseudo chiral carbon
atom while the other two are usual chiral carbon atoms.

8. Molecular formula.

9. Non-superimposable on its mirror image.

10. Cyclohexane (iv) is non-planar and has chair conformation. In this conformation,
the C C C bond angle are the normal tetrahedral angles (109º-28’) and thus
has no angle strain and hence is the most stable. The rest of the molecules are
nearly planar and hence their stability depends upon the angle strain in
accordance with Baeyer’s strain theory. Since cyclopropane has higher angle
strain (24º– 44’) than cyclopentane (0º – 44’),
therefore, cyclopentane (iii) is more stable than cyclopropane (ii). Further,
because of the presence of a double bond in a three-membered ring,
cyclopropene (ii) is the least stable. Thus, the order of stability is (iv) > (iii) > (i) >
(ii).


11. CH 2
CHCH O H   C H 3 has a chiral carbon atom

12. C60 isotope of carbon is called fullerence.

13. Since all the six carbon atoms of cyclohexatriene (benzene) are sp2-hybridized,
THE GUIDANCE 58/1, Kalu Sarai, Sarvpriya Vihar, New Delhi-16, Ph: 41828089, 46043741 (11)
 therefore, its stablest structure is planar form.

14. Three, These are : CH3OCH2CH2CH3,

CH3-O-CH(CH3)2 and CH3CH2OCH2CH3.

15. Structures (a), (c) and (d) have the same M.F. (C6H12O) as that of
CH3COCH2CH2CH2CH3 and hence are all isomers.The M.F of structure (b) is
C6H10O and hence it is not an isomer.

16. 1 and 2 represent staggered conformation.

17. meso-Tartaric acid optically inactive due to molecular symmetry because of the
presence of a plane of symmetry in its molecule.

18. Resolution.

19. Try Your Self

-
20. Since during the reaction, a chiral carbon is created and further since the CN ion
can attack the planar aldehyde group both from the top and the bottom face of
the aldehyde group with equal ease, therefore, a 50:50 mixture of the two
enantiomers,i.e. a racemic mixture is obtained.

21. trans-2-Butene has zero dipole moment.

22. Three. These are: d-tartaric acid, l-tartaric acid and meso-tartaric acid.

23. Six.These are: 1-butene, trans-2-butene, cis-2butene, 2-methyl propene

24. The two compounds are non-superimposable mirror images of each other and
hence are enantiomers.

25. Monochlorination of 2-methylbutane gives four isomers:

(i) (ii)

(iii) (iv)

THE GUIDANCE 58/1, Kalu Sarai, Sarvpriya Vihar, New Delhi-16, Ph: 41828089, 46043741 (12)
 Out of these only (i) and (iv) are optically active and hence gives only two
enantiomeric pairs.

26. Rotation of B through 180º within the plane of the paper gives D which is an
enantiomer of (A) .

Thus,A and B are enantiomers.

* *
27. Butane-2, 3-diol (C H 3  C H O H  C H O H  C H 3 ) ) has two similar chiral carbon
atoms. Therefore, like tartaric acid it has three stereoisomeric forms (d-, l -and
meso ) Out of these only two (d -andl ) are optically active

28. Conformers.

29. Staggered – anti.

30. The two compounds are identical since they have a plane of symmetry.

31. Boat conformation of cyclohexane has two types of destabilizing intereactions,

i.e, eclipsing and flagpole-flagpole. Out of these eclipsing interactions are the
most destabilizing.

32. Only DCH2CH2CH2Cl does not contain a chiral carbon and hence it is not chiral

33. As the size of the ring increases, the internal angle increases accordingly. As a
result, the derivation from the tetrahedral angle and hence the angle strain
increases as the size of the ring increases. Thus planar cyclodecane is
expected to have the maximum angle strain.

34. The configuration of the penultimate carbon of any optically active compound
is always correlated with D (+)-glyceraldehyde.
Therefore, option (c) is correct.

35. The two compounds are non-superimposable mirror images of each other and
hence are enantiomers.

36. Both the C-atoms of the double bond of 1-phenyl-2-butene

(C 6 H 5 C H 2  C H  C H  C H 3 ) carry different substituents and hence it shows
THE GUIDANCE 58/1, Kalu Sarai, Sarvpriya Vihar, New Delhi-16, Ph: 41828089, 46043741 (13)
 geometirical isomerism.

37. The given compound contains a double bond (with different substituents on
each carbon) as well as a chiral carbon, therefore, it shows both geometrical as
well as optical isomerism.

38. (R)- and (S)- enantiomers differ only in their behaviour towards plane polarized
light.

39. Restricted rotation around C=C bond .

40. Convert these Newmann projections into open chain structures:

Structures I and II being position isomers are, in fact, structural isomers.

41. Putting a substituent at position 3 will make the molecule chiral

42. Three: CH3OCH2CH2CH3,CH3CH2OCH2CH3CH3OCH (CH3)2

43.

Due to cis -addition of H2 to the triple bond, the reduced product has a plane of
symmetry and hence is optically inactive.

44. Six, these are:

THE GUIDANCE 58/1, Kalu Sarai, Sarvpriya Vihar, New Delhi-16, Ph: 41828089, 46043741 (14)
45. 2-Methylbutanoic acid has a chiral carbon and hence is

optically active.

46. CH3–C  C–CH3 being linear as well as symmetrical, has lowest dipole moment.

47. II and IV and cis-trans-isomers

48. Both are included in stereoisomerism

49. 1,1-Dichloro-1-pentene
does not show geometrical isomerism since it has
tow identical atoms i.e. Cl on C1.

50. Following the procedure outlined under ‘Golden Rule’ the absolute configuration
is 2S, 3S.

51. I and II contain chiral C-atoms and hence are chiral compounds

52. Try Your Self.

53. Twelve in all. These are (a) Six geometrical isomers :

THE GUIDANCE 58/1, Kalu Sarai, Sarvpriya Vihar, New Delhi-16, Ph: 41828089, 46043741 (15)
 (b) Two optical isomers

(c) Four structural isomers

C lC H 2
C H 2  C H  C H 2
(x ii )

54. All the three exhibit conformational isomerism due to rotation about C-O
bond in CH3OH, O-O bond in H2O2 and N-N bond in NH2–NH2.

55. Disubstituted cyclic compounds and disubstituted alkenes show geometrical

isomerism. Therefore, option (d) correct.

56. abd C-C abd has three stereoisomeric forms, i.e d-form, l-form and meso- form
but (only two of these, i.e., d-and l-forms are optically active.

57. Enantiomers have same m.p./b.p and refractive indices but rotate plane
polarized light in opposite directions but to the same extent.

58. (+) and(-) Lactic acid on treatment with an optically active base such as (+) or (-)
brucine to form diastereomers which have different m.p/b.p and solubilities and
hence can be separated

59. Compounds possessing one chiral carbon atom are always optically active.

60. Glycine is optically inactive but alanine is optically active, Therefore, the
dipeptide glycylalanine is also optically active.

THE GUIDANCE 58/1, Kalu Sarai, Sarvpriya Vihar, New Delhi-16, Ph: 41828089, 46043741 (16)
61.

(c) has a centre of symmetry and hence is optically inactive .

62.

63. The configuration about the double bond is Z and hence the correct name is (Z)-
4, 6-dimethyloct-4-en-3-one.

64. The configuration about the double bond is (E) while that around the chiral
centre, i.e. C5 is S.

Hence the correct name is (S) – 5-bromo-(E)-hex-3-en-2-one.

65. Apply Golden rule to the four compounds.

THE GUIDANCE 58/1, Kalu Sarai, Sarvpriya Vihar, New Delhi-16, Ph: 41828089, 46043741 (17)
66. Apply Golden rule to all the four compounds.

67. In compound (d), the two identical atoms (H,H) or groups (OH,OH) lie on the
same side of the Fischer projection formula and hence it represents the erythro
isomer.

THE GUIDANCE 58/1, Kalu Sarai, Sarvpriya Vihar, New Delhi-16, Ph: 41828089, 46043741 (18)