69

DROPPER 2022
ISOMERISM
STEREOISOMERISM

Marking Scheme : Single Correct (+3,-1) M M: 584 Time : 7 hr

Objective : SCQ
1. Stereoisomers have different :
(a)Molecular formula (b) Structural formula (c) Configuration (d) Molecular mass
2. Which can show the cis-trans isomerism :
(a) ClCH2CH2Cl (b) Cl2C==CH2 (c) Cl2C==CCl2 (d) ClCH==CHCl
3. Which of the following compounds will not show geometrical isomerism :
(a)Azomethane (b) 1-Bromo-2-chloroethene (c) 1-Phenylpropene (d) 2-Methyl-2-butene
4. Which of the following compound can not show geometrical isomerism ?

(a) (b) (c) (d)

5. Identify (Z) - 2 - pentene :

(a) (b) (c) (d)

H H
6. The ‘E’-isomer is/are :
H C2H 5
(a) (b) (c) C C (d)
||

H3C CH(CH3) 2

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

(a) > (Melting point)

(b) < (Dipolemoment)

(c) > (Boiling point)

(d) > (Water solubility)

8. Chiral molecules are :

(a) Superimposable on theirmirror image (b) Not superimposable on their mirror image
(c) unstablemolecules (d) capable of showing geometrical isomerism
9. Number of chiral carbon persent in the following compound : CH3 CH CH 3 CH CH CH 3

OH Br C5H5
(a) 2 (b) 3 (c) 4 (d) 5

24
10. The compound which has maximum number of chiral centres is

(a) (b) (c) (d)

11. Which of the following is the structure of (S)-Pentan-2-ol is ?

(a) (b) (c) (d)

12. The configuration of the given compound is :

(a) E (b) R (c) S (d) Z

13. Which Fisher projection represents the given wedge dash structure :

(a) (b) (c) (d)

14. Which of the following have same configuration.

F Br H

(I) C H (II) C Cl (III) C Br

Cl Br H F F Cl
(a) I & II (b) II & III (c) I & III (d) All
15. Which has D configuration.
CH3 OH CH3 COOH

(a) HO H (b) H COOH (c) H OH (d) H 2N H

COOH CH3 CHO CH3

16. Which of the following compound posses plane of symmetry ?

(a) (b) (c) (d)

17. Which of the following compound posses centre of symmetry ?

O CH3
H
H N –C CH3 H OH
(a) (b) H C C –N H (c) OH H (d)
3
H CH3
O
18. Which of the following are chiral :

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

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

25
19. Which is not the pair of enantiomers ?

(a) (b)

(c) (d)

20. Which of the following pairs of compounds are enantiomers :

CH3 CH3 CH3 CH3
H OH HO H H OH HO H
(a) and (b) and
HO H H OH HO H HO H

CH3 CH3 CH3 CH3

CH3 CH3 CH3 CH3
H OH H OH HO H HO H
(c) HO H
and (d) H OH
and HO H
H OH
CH3 CH3 CH3 CH3
21. Stereoisomers which are not mirror image of each other, are called :
(a) Enantiomers (b) Tautomers (c) Meso (d) Diastereomers
22. Which one among the following is not diastereomeric pair.

(I) (II) (III) (IV)

(a) I and III (b) I and II (c) II and III (d) I and IV
23. What is the relationship between (I) & (II)
(I) (II) (a) Enantiomer (b) Diastereomers

(c) Constitutional isomer (d) Identicalmolecules

24. and are

(a) Enantiomers (b) Optical inactive diastereomers (c) Optical active diastereomers (d) Identical
25. The instrument which can be used to measure optical activity, i.e., specific rotation:
(a)Refractometer (b) Photometer (c) Voltmeter (d) Polarimeter
26. (+) tartaric acid has a specific rotation of + 12 unit when measured in 12 cm polarimeter tube and 2g/ml
concentration at given temperature and light.When it is diluted to half the concentration, length of tube
and other parameters being same, then the specific rotation will be :
(a) + 6 unit (b) + 12 unit (c) –6 unit (d) + 24 unit

27. If optical rotation produced by is + 36° then that produced by is:

(a) –36° (b) 0° (c) +36° (d) unpredictable

26
28. The enantiomeric excess and observed rotation of a mixture containing 6 gm of (+)-2-butanol
and 4 gm of (–)-2-butanol are respectively (If the specific rotation of enantiomerically pure
(+)-2-butanol is + 13.5 unit).
(a) 80%, + 2.7 unit (b) 20%, – 27 unit (c) 20%, + 2.7 unit (d) 80%, – 27unit
29. The racemic mixture of Alanine CH 3 CH COOH can be resolved by using,

NH2
(1) (+)-2-Butanol (2) (l)-2-Chlorobutanoic acid (3) (±)-2-Butanol (4) (dl mix)-2-Chlorobutanoic acid
(a) 1 & 2 only (b) 1 & 3 only (c) 2 & 4 only (d) 3 & 4 only
30. Themajor product (ester) of the following reaction is

H SO
+ 2 
4


(a) A single stereoisomer (optically active) (b) A mixture of diastereomers (both optically active)
(c) A racemic mixture (optically inactive) (d) A mixture of four stereoisomers (two racemic mixtures)
31. Which of the following pair of isomers can not be separated by fractional crystallisation or fractional
distillation:
(a) Maleic acid and Fumaric acid (b) (+)-Tartaric acid and meso-tartaric acid
(c) CH 3 CH COOH and H2N—CH2—CH2—COOH (d) (+)-lactic acid and (–)-lactic acid

NH2
32. Which of the following amine is optically active ?
CH 3
(a) CH3NH2 (b) CH3NHC2H5 (c) CH3CH2CH2 N (d) sec-Butylamine
C2 H5

33. The followingmolecules are:

(a) Enantiomers (b) Diastereomers (c) Identical (d) Conformers

34. How many geometrical isomers are possible for the given compound.
Ph—CH==CH—CH==CH—COOH
(a) 2 (b) 4 (c) 6 (d) 8
35. How many geometrical isomers are possible for the given compound.
CH3—CH==CH—CH==CH—CH==CH2
(a) 2 (b) 3 (c) 4 (d) 8
36. How many geometrical isomers are possible for the given compound.

(a) 2 (b) 4 (c) 6 (d) 8

37. Total number of stereoisomers of compound is :
CH 3 CH CH CH 3

OH Br
(a) 2 (b) 4 (c) 6 (d) 8

27
38. Total number of optically active stereoisomers of tartaric acid is
(a) 2 (b) 4 (c) 3 (d) 0
39. Number of fractions on fractional distillation of mixture of :

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

40. Total number of optically active stereoisomers of CH 3 CH CH CH CH 3

Cl Cl Cl
(a) 2 (b) 4 (c) 6 (d) 8
41. The total number of ketones (including stereo isomers) with themolecular formula C6H12O is :
(a) 4 (b) 5 (c) 6 (d) 7
42. Total number of optical active stereoisomers of the following compound is :
CH3—CH==CH—CHCl—CH==C==CH—CH==CH—CH3
(a) 8 (b) 6 (c) 16 (d) 10
43. The eclipsed and staggered conformation of ethane is due to .
(a) Free rotation about C—C single bond (b) Restricted rotation about C—C single bond
(c)Absence of rotation about C—C bond (d) None of the above
44. Which of the following is associated with Torsional strain ?
(a) Repulsion between bond pair of electrons (b) Size of the groups present at adjacent atoms
(c) Bond angle strain (d)Attraction of opposite charges
45. The Baeyer’s angle strain is expected to be maximum in
(a) Cyclodecane (b) Cyclopentane (c) Cyclobutane (d) Cyclopropane
46. In the following the most stable conformation is :

(a) (b) (c) (d)

47. Which of the following is an achiral molecule?

(a) (b) (c) (d)

48. In 2-Fluoroethanol which conformer will be most stable ?

(a) Eclipsed (b) Skew (c) Gauche (d) Staggered

28
49. The true statement about the following corformation is :
(a) It has maximum angle strain.
(b) It does not have eclipsing strain (tortional strain).
(c) It does not have any intramolecular hydrogen bonding.
(d) It has maximum vander waal strain.

50. and are

(a) Enantiomers (b) diastereomers (c) Identical compounds (d) Conformers

51. The least stable conformation of cyclohexane is
(a) Boat (b) Chair (c) Twist boat (d) Half chair
52. Flagpole interaction is present in :
(a) Boat form of cyclohexane (b) Chair form of cyclohexane
(c)Anti form of n-butane (d) Fully eclipsed form of n-butane
53. Chair form of cyclohexane is more stable than boat form because :
(a) In chair form carbons are in staggered form and in boat form carbons are in eclipsed form
(b) In chair form carbons are in eclipsed form and in boat form all the carbons are in staggered form
(c) Bond angle in chair form is 111° and bond angle in boat form is 109.5°
(d) Bond angle in chair form is 109.5° and in boat form 111°
54. The most stable form of trans-1,4-dimethylcyclohexane is represented as :
CH3
H 3C
(a) (b) (c) CH3 (d)
CH3
55. Geometry of the given compound is:

(a) Cis (b) Trans

(c) Cis and trans both (d) No geometrical isomerism

56. The most stable form of cis cyclohexane-1,3-diol is represented as :

OH OH
(a) (b) (c) (d)

57. Which of the following molecule is chiral.

Cl H H Cl

Cl Cl Cl Cl
H H
(a) (b) H (c) (d)
Br
Cl
H H Cl Cl Br

29
58. Which one of the following compounds will show enantiomerism ?
O
— OH O
(a) CH 3— —CH3 (b) H 3C — —CH3 (c) (d) — OH

—
HO—H 2C O
59. Number of conformational isomers of ethane
(a) 7 (b) 3 (c) 4 (d) Infinite
60. Which of the following statement regarding the projections shown below is true ?
(a) ‘a’ and ‘b’ both represent the same configuration
(b) Both ‘a’ and ‘b’ are optically active
(c) ‘b’ alone is optically active
(d) ‘a’ alone is optically active

61. The structures and represents

(a) geometrical isomers (b) positional isomers (c) conformational isomers (d) configurational isomers
62. The given compound has :

(a) chirality (b) superimposability on its mirror image isomer

(c) plane of symmetry (d) C2 axis of symmetry

63. The compounds X and Y in below reaction can be:
Ph—NH.NH2 + (X) + (Y) – H O(P) + (Q) [both organic products]
2

(a) CH3—CH2— C —CH3 + CH3— C —Ph (b) Ph— C —CH3 + CH3CHO

|| || ||
O O O
(c) CH2==O + CH3CHO (d) CH2==O + CH3— C —CH3
||
O
64. No. of Geometrical isomers for following compound is:
CH3
(a) 8 (b) 16
CH2 CH CH CH N OH (c) 32 (d) 10
65. How many stereoisomers are possible for?

(a) 128 (b) 64 (c) 32 (d) 16

66. How many spatial orientations are possible in the following compound ?

(a) 2 (b) 8 (c) 6 (d) 4

30
67. Racemic mixture is formed by mixing two: [AIEEE 2002]
(a) Isomeric compounds (b) Chiral compounds (c) Meso compounds (d) Optical isomers
68. Which of the following does not show geometrical isomerism ? [AIEEE 2002]
(a) 1,2-Dichloro-1-pentene (b) 1,3-Dichloro-2-pentene
(c) 1,1-Dichloro-1-pentene (d) 1,4-Dichloro-2-pentene
69. Among the following four structures I to IV. [AIEEE 2003]

(I) (II) (III) (IV)

it is true that
(a)All four are chiral compounds (b) Only I and II are chiral compounds
(c) Only III is a chiral compound (d) Only II and IV are chiral compounds
70. Which of the following will have a meso-isomer also ? [AIEEE 2004]
(a) 2-Chlorobutane (b) 2,3-Dichlorobutane (c) 2,3-Dichloropentane (d) 2-Hydroxypropanoic acid
71. Amongst the following compounds, the optically acitve alkane having lowest molecular mass is

CH3 H [AIEEE 2004]

| |
(a) CH3—CH2—CH2—CH3 (b) CH3—CH2—CH—CH 3 (c) CH3—C— (d) CH3—CH2—CCH
|
C2H5
72. Which of the following compounds is not chiral ? [AIEEE 2004]
(a) 1-Chloropentane (b) 2-Chloropentane
(c) 1-Chloro-2-methylpentane (d) 3-Chloro-2-methylpentane
73. Which type of isomerism is shown by 2,3-dichlorobutane ? [AIEEE 2005]
(a) diastereomerism (b) optical-isomerism (c) geometric-isomerism (d) structural-isomerism
74. Increasing order of stability among the threemain conformations (i.e. eclipse, anti, gauche) of 2-fluoroethanol
is: [AIEEE 2006]
(a) eclipse, gauche, anti (b) gauche, eclipse, anti (c) eclipse, anti, gauche (d) anti, gauche, esclipse
75. Which of the following molecules is expected to rotate the plane of polarized light? [AIEEE 2007]

(a) (b) (c) (d)

76. Which one of the following conformations of cyclohexane is chiral? [AIEEE 2007]
(a) Chair (b) Boat (c) Twist boat (d) Rigid
CO2 H
HO2C
77. The absolute configuration of HO is: [AIEEE 2008]
H H
OH
(a) R, R (b) R, S (c) S, R (d) S, S

31
78. The alkene that exhibits geometrical isomerism is: [AIEEE 2009]
(a) 2-methyl propene (b) 2-butene (c) 2-methyl-2-butene (d) propene
79. The number of stereoisomers possible for a compound of themolecular formula
CH3—CH==CH—CH(OH)—Me is: [AIEEE 2009]
(a) 2 (b) 4 (c) 6 (d) 3
80. Out of the following, the alkene that exhibits optical isomerism is: [AIEEE 2010]
(a) 3-methyl-2pentene (b) 4-methyl-1-pentene (c) 3-methyl-1-pentene (d) 2-methyl-2-pentene
81. Which of the following compound will exhibit geometrical isomerism ? [JEE(Main) 2015]
(a) 1-Phenyl-2-butene (b) 3-Phenyl-1-butene (c) 2-Phenyl-1-butene (d) 1,1-Diphenyl-1-propane
82. An enantiomerically pure acid is treated with racemic mixture of an alcohol having one chiral carbon.
The ester formed will be: [IIT-JEE-2003]
(a) Optically active mixture (b) Pure enantiomer (c) Meso compound (d) Racemic mixture
83. Statement-1 : Molecules that are not superimposable on their mirror images are chiral. because
Statement-2 : All chiral molecules have chiral centres. [IIT-JEE-2007]
(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.
84. The number of optically active products obtained from the complete ozonolysis of the given compound
is: CH H [IIT-JEE-2012]
3

CH3 CH CH C CH CH C CH CH CH 3

H CH 3
(a) 0 (b) 1 (c) 2 (d) 4

32
 Objective : MCQ
85. Which of the following will form only one oxime on reaction with NH2OH solution ?

(a) (b) (c) (d)

86. Which of the following compounds will show optical activity ?

(a) (b) (c) (d)

87. Which of the following is/are chiral ?

(a) (b)

H Br
(c) (d)
Br H
88. What should be the minimum conditions to show geometrical isomerism ?
(a) Restricted rotation about double bond or ring.
(b) Groups which are responsible to show geometrical isomerism differ in their relative distance.
(c) Free rotation about single bond.
(d) Two different groups at both restricted atoms.
89. Which of the following compounds has cis configuration at each double bond ?

(a) (b)

(c) (d)

90. Which of the following carbonyl compounds can give two oximes on reaction with hydroxyl amine ?
(a) HCHO (b) CH3CHO (c) PhCHO (D) CH3COPh
91. Which of the following is true for maleic acid and fumaric acid.
(a) Configurational isomers (b) Stereo isomers (c) Z and E isomers (d) Constitutional isomers
92. Which of the following is correct statement :
(a) Geometrical isomers are notmirror image isomer.
(b) Acompound having double bond (restricted bond) always show geometrical isomerism.
(c) Acyclic compoubd having single bond does not show geometrical isomerism.
(d) Cyclodecene can show cis & trans form.
93. Which of the following statement(s) is/are correct for given compound:
(a) It is a optically active compound
(b) It can show geometrical isomerism
(c) It posses centre of symmetry but not plane of symmetry.
(d) It is a meso compound

33
94. Find out correct statement/s.
(a) All chiral centers are stereogenic centers. (b) All stereogenic centers are not chiral center.
(c) Acompound may be chiral without chiral center.
(d) A compound will be chiral only if it has at least one chiral center.
95. Which is/are not the structure of 3-Methyl butan-2-ol.

(a) (b) (c) (d)

96. Fischer projection formula of this compound can be represented as :

H
OH
C2H5 C
(a) (b) (c) (d)
H C
CH3 OH
97. Which of the following compounds will have C2 axis of symmetry ?

(a) (b) (c) (d)

98. H is :
H 3C H
(a) optically active molecule. (b) having plane of symmetry.
(c) having axis of symmetry. (d) having centre of symmetry
H2N CH3
H
99. The correct relation between compound(s) I and II is/are
(I) (II)
(a) identical. (b) diastereomers.
(c) enantiomers. (d) configurational isomers

100. Enantiomers have

(a) Similar physical properties (generally).
(b) Similar chemical properties with optical active compounds.
(c) Same absolute value of specific rotation. (d) Different configurations.
101. Which of the following will show geometrical isomerism?

(a) CH3—CH==C==C==CH—CH3 (b)

(c) (d)

34
102. The correct statement(s) about the compound given below is/are: [IIT-JEE-2008]

(a) The compound is optically active (b) The compound possesses centre of symmetry
(c) The compound possesses plane of symmetry (d) The compound possesses axis of symmetry
103. The correct statement(s) about the compound H3C(HO)HC—CH==CH—CH(OH)CH3 (X) is/are:
[IIT-JEE-2009]
(a) The total number of stereoisomers possible for X is 6.
(b) The total number of diastereomers possible for X is 3.
(c) If the stereochemistry about the double bond in X is trans, the number of enantiomers possible for X is 4.
(d) If the stereochemistry about the double bond in X is cis, the number of enantiomers possible for X is 2.
104. Amongst the given options, the compound(s) in which all the atoms are in one plane in all the possible
conformations (if any), is/are: [JEE-2011]

(a) (b) H C (c) H2C==C==O (d) H2C==C==CH2

105. Which of the given statement(s) about N, O, P and Q with respect to M is/are correct ?
[IIT-JEE-2012]

(a) M and N are non-mirror image stereoisomers (b) M and O are identical
(c) Mand P are enantiomers (d) M and Q are identical
106. Compound(s) that on hydrogenation produce(s) optically inactive compound(s) is/are:
[JEE(Advanced)-2015]
H Br
H Br H Br H 2C Br H
(a) (b) H 2C CH3 (c) CH3 (d) H 2C CH3
H 3C CH3 CH 3

35
 Integer
107. How many cyclic and acyclic structural isomers of C5H10 can show geometrical isomerism?
108. In given compounds how many can show geometrical isomerism-

(i) (ii) (iii) (iv)

109. In given compounds howmany have Z configuration along double bond ?

(i) (ii)

(iii) (iv)

Cl

110. Sum of C2 & C3 axis of symmetry is:

Cl Cl
111. Optical rotaion data are expressed in standard way (specific rotation []D).
If magnituted of specific rotation of isomer d-lactic acid is 3.82. What will be the magnitude of
specific rotation of acetic acid in degree.
112. How many of the following are cis dichlorocyclohexane.

(i) (ii) (iii) (iv)

(v) (vi) (vii) (viii)

113. How many of the following are (configurational) enantionmers of (A) ?

(A) =

(p) (q) (r) (s) (t)

114. Pure cholesterol has a specific rotation of –32. A sample of cholesterol prepared in the lab has a specific
rotation of –8. The enatiomeric excess of the sample of chloresterol is x%. x is :
OH

115. Pure (R) Mandelic acid COOH has specific rotation of –150. If a smaple contains 60% of the

R and 40% of its enantiomer, then []D of this solution is.

36
116. Total number of geometrical isomers in the given compound are:

C CH DC CD HC C

117. Total number of geometrical isomers in the given compound are:

CH C C C C CH

D H H D
118. Total number of stereoisomers of compound CH3 CH CH CH CH CH CH 3 are :

Cl
119. Total number of optically active stereoisomers of CH3 CH CH CH CH CH 3 are :

Cl Cl
120. For the compound A—CH2—CH2—A draw the newmann projection formula of all the stable
conformational isomers if obs = 2D and Xanti = 0.75 then find gauche. (If A = NO2)
121. Total number of stereoisomers possible for the given structure excluding the configurationmentioned is :

122. Observe the compound ‘M’

M= If in this compound
X = Total number of asymmetric C* atoms
Y = Number of similar asymmetric C* atoms
Z = Number of optically active stereoisomers
W = Number of opticaly inactive isomers
R = Number of geometrical orientations in space
Report your answer as : X + Y + Z + W + R
123. The total number of cyclic structural as well as stereo isomers possible for a compound with the molecu-
lar formula C5H10 is: [IIT-JEE-2009]
124. The total number(s) of stable conformers with non-zero dipole moment for the following compound is/
are: [JEE(Advanced)-2014]

125. The total number of stereoisomers that can exist for M is: [JEE(Advanced)-2015]

37
 Subjective
126. Which of the following compounds have restricted rotation and out ofwhich can showgeometrical
isomerism?

(i) (ii) (iii) ClCH==CHCl (iv) Ph—N==N—Ph

(v) CH3CH==C(CH3)2 (vi) CH3CH==CH2 (vii) CH3CH==CHCH3 (viii) CH3—C==C—CH3

127. Write the essential conditions for geometrical isomerism.
128. Define restricted rotation and give one example each of acyclic and cyclic compound, which can show
geometrical isomersm.
129. Which of the following can show geometrical isomerism.
H OH
(i) (ii) (iii) (iv) C N
CH 3
Cl H
H
C C
(v) (vi) CH3 (vii) CH3 (viii) CH2=CH–CH=CH–Ph
Cl Cl
130. Which of the following carbonyl compound will give two products after reaction with NH2OH:
O CHO
(i) (ii) CH3—CHO (iii) (iv) DCHO (v) (vi)

131. Indicate whether each of the following compound is ‘E’ or ‘Z’.

(i) (ii) (iii) (iv)

132. (a) BrHC==CHBr exists as two diastereomers draw them and compare their dipole moment.
(b) trans-Butenedioic acid has higher melting point than cis-butenedioic acid. Why ?
(c) Draw the cis and trans structures of hex-2-ene.Which isomer will have higher b.p. and why ?
133. Number of chiral carbon atoms in the compound w, x, y and z respectively would be:

(w) (x) (y) (z)

134. Howmany number of chiral centres present in the following compounds ?

C H2OH
O
H OH
H
OH H
HO

H OH
(i) O D(+)-Sucrose (ii)
HO H2C O

H H HO
CH2 O H

OH H

38
135. Find R/S configuration of following compounds.
COOH
CHO COOH COOH
H OH
(I) H OH (II) HO H (III) H NH 2 (IV)
HO H
CH2OH CH3 CH 3
COOH
136. Find D/L configuration in the followingmolecules.
CHO
COOH
H OH
(I) H OH (II) H OH (III)
CH 3 CH2—OH
137. The R/S configuration of following compounds are :

(i) (ii) (iii) (iv)

138. Find plane of symmetry and centre of symmetry (if possible) in the following compounds.

(I) (II) (III) (IV) (V)

139. Find plane of symmerty, centre of symmerty and axis of symmetry (if possible) in the following molecules.

Cl Cl
(i) (ii) (iii)
H H

Br H
(iv) (v) (vi)
H Br

140. Identify the pairs of enantiomers and diastereomers from the following compounds I, II and III :
CH 3 CH 3 CH 3
H OH HO H HO H
(I) HO H (II) HO H (III) H OH
CH 3 CH 3 CH 3
141. Find relationship between the given pairs.
F I
F Br
(I) Br (II) H Cl and D F
Cl and I F
D I Br H
I Cl
Br Cl
COOH COOEt COOH COOH
H OH
(III) and H OH
(IV) H OH
and HO H
HO H HO H HO H H OH
COOEt COOH COOH COOH

39
142. Give the relationship between the following pairs of compounds.
CH 3 CH3
H OH H OH
(a) and (b) H Cl and Cl H
H OH H OH
C 2H5 C2H 5

(c) and (d) and

H CH3 CH3 H H CH3

C C C

143. (I) (II) (III)

Cl Br Br Cl Cl Br
(i) Total number of fractions on fractional distillation of I, II and III. (ii) Optical active compounds.
(iii) Relation between I and II. (iv) Relation between I and III.
144. What does D/L & d/l represent.
145. Write the definition of specific rotation.
146. Write the formula for optical purity & enantiomeric excess.
147. The total number of fractions (n) obtained in the following reaction is:

148. Which of the following are chiral compound?

O CH3 Me
O || |+ |
S P Cl H H
(i) (ii) (iii) N (iv) Si
Me Et C2 H5O Br Et D Et Ph
CH3
|+
(v) C (vi)
C2H5 H
149. Which of the following are chiral molecules?
(i) Ph—CH==C==C==CH—Cl (ii) CH3—CH==C==C==C==CH—CH3
H Br
(iii) (iv)
Br H
Br
(v) (vi)
Cl Cl
150. Find the number of geometrical isomers possible of the following compounds.
(i) (ii)
(iii) (iv)
151. How many n-octene can show geometrical isomerism ?
152. How many geometrical isomers are possible for Hepta-2, 5-dienoic acid:

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153. For the given compound CH3 CH CH CH CH3

OH
(I) Total number of stereoisomers. (II) Number of optically active stereoisomers.
(III)Total number of fractions on fractional distillation of all stereoisomers.
154. The number of isomers for the compound with molecular formula C2BrClFI are :
155. Draw the most stable conformation of meso-CH3CHD—CHDCH3
156. Consider all types of C—C bond rotation in following molecule.
CD 3
| Howmany number of different types of eclipsed conformations are possible ?
H3C C CF3 Draw Newman conformations of all eclipsed form.
|
CCl 3
157. Write the most polar and most stable conformer of 1-nitropropane.
158. Draw themost stable conformer of 3-hydroxypropanal.
159. Write the newman projection formula of the following compounds
(I) Cl—CH2—CH2—CH3 in itsmost polar form.
(II) HO—CH2—CH2—OH in its most stable form.
(III) HOOC—CH2—CH2—COOH in its least stable staggered form.
160. Draw themost stable newman projection formula along C1—C2 bonds of following compounds.
CH 3

(i) CH3 CH 2 CH 3 (ii) CH3 CH CH 3 (iii) CH3 C CH 3

CH 3 CH 3
CH 3 CH 3 OH OH

(iv) CH3 CH CH CH3 (v) HO CH CH F (vi) COOH CH CH COOH

161. Which of the following combination of axial & equitorial bonds show Cis or Trans orientation in Dimethyl
cyclohexane?
(i) 1e, 2e (ii) 1e, 3e (iii) 1e, 4e (iv) 1e, 2a (v) 1e, 3a (vi) 1e, 4a (vii) 1a, 3a
162. Which one is more stable and why ?

(I) (II)

163. It is given that for conformational isomers, the net dipole moment is obs =  ixi
where obs = obsereved dipolemoment of the compound
i = dipole moment of the stable conformational isomers; xi = mole fraction of stable conformers
for the compound Z—CH2—CH2—Z draw the Newman projection formula of all the stable conforma-
tional isomers, if obs = 1D, and xanti = 0.82, and find gauche. Now draw the Newman projection formula
of the most stable conformation of meso Y—CHD—CHD—Y.
(a) If Y is CH3 (rotation about C2—C3 bond)
(b) If Y is OH (rotation about C1—C2 bond) [IIT-JEE-2005]

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 Comprehension
 Different arrangements of atoms that can be converted into one another by rotation about single bonds
are called conformations. The energy required to rotate the molecule about carbon-carbon bond is
called torsional energy. When size and number of groups increases torsional energyalso increases. In
staggered conformation Van der Waal’s and torsional strains are less so these conformations are
relatively more stable.
164. Which conformation has maximum energy?
OH OH OH OH
NO2 H
H NO 2 H H
(a) (b) (c) (d)
H H
CH 3 H Me H Me H Me H
H NO2
H NO2
165. In which conformation torsional strain (rotational barrier) is minimum?

CH 3 H H H CH 3
H 3C CH 3 H 3C CH 3 H H H H

(a) (b) (c) (d)

H 3C CH 3 H H H H H H
CH 3 CH 3 H H H

 Tartaric acid [HOOCCH(OH)CH(OH)COOH] was an important compound in history of stereo-

chemistry. Two naturally occuring forms of tartaric acid are optically inactive. One optically inactive
form (P) has a melting point of 210-212°C and can be separated into two optically acitve forms,
whereas other optically inactive form (Q) cannot be resolved further.
166. Optically inactive form Q is
COOH COOH COOH
H OH HO H HO H
C C C
(a) (b) (c) (d) none of these
C C C
HO H HO H H OH
COOH COOH COOH
167. An optically inactive form P is :
(a) Optically inactive due to internal compensation.
(b) Optically inactive due to presence of plane of symmetry.
(c) Optically inactive due to external compensation.
(d) Optically inactive due to intramoleuclar hydrogen bonding.

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 Column Match
168. Column-I Column-II

(a) (p) Chiral Molecule

(b) (q) Achiral Molecule

(c) (r) Plane or centre of symmetry present

(d) (s) Axis of symmetry present (except C1).

169. Column-I Column-II

OH OH
H OH H H
(a) and (p) I st is more stable in the given form.
H H H H
H OH
COOH COOH
H COOH H H
(b) and (q) I, II are conformational diastereomers.
H H H H
H COOH
Me Me
D H H D
(c) and (r) IInd is more stable in the given form.
D H D H
Me Me
CHO CHO
H NH2 H H
(d) and (s) dipolemoment of I is more than II.
H H H H
H NH2

(t) I, II are configurational diastereomers.

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170. Column-I Column-II

CH3
H

(a) (p) Conformation with minimum vander-waal strain

H
H 3C H
H3C

CH 3
CH 3

(b) (q) Conformation with maximum vander waal strain

H
H CH 3
H
CH3
H H
(c) (r) Conformation of maximum torsional strain
H H
CH 3
CH3
H CH 3
(d) (s) Conformation with minimum torsional strain
H H
H

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All students are advised to solve DPPs within allowed time only.
All discussions are scheduled in every 4th doubt discussion class
–MKA Sir (Guruji)

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