IsomerismDPP EvolveBatch

CONTENT
S.No Pages
DPP-1 Optical Isomer, Chiral centre 04 – 10
DPP-2 R S Nomenclature 11 – 17
DPP-3 Racemic Mixture 18 – 19
DPP-4 Enantiomer 20 – 24
DPP-5 D L Nomenclature 25 – 28
DPP-6 Diastereomer 29 – 38
DPP-7 Plane of symmetry 39 – 44
DPP-8 Centre of symmetry 45 – 49
DPP-9 Axis of symmetry 50 – 55
DPP-10 AAOS 56
DPP-11 Chiral, Achiral 57 – 65
DPP-12 Meso 66 – 68
DPP-13 Calculation of Optical 69 – 74
DPP-14 Calculation of stereoisomer, Part - 1 75 – 80
DPP-15 Calculation of stereoisomer, Part - 2 81 – 83
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Single Choice Question
1. Which of the following have asymmetric carbon atom?
(A) (B) (C) (D)
2. Which of the following given compound have even number of chiral center ?
(A) (B)
(C) (D)
3. Find the sum of all the stereocenters that are present in below compounds :
CH3 CH3 CH3 CH3

H H H H
CH3 CH3 CH3 CH3
H H CH3 CH3
H H
CH3 CH3
(I) (II) (III) (IV)
(A) 8 (B) 9 (C) 10 (D) 11
4. An alkane can show structural isomerism if it has ......... number of minimum carbon atoms
(A) 1 (B) 2 (C) 3 (D) 4
5. How many chiral carbons are there in reserpine (an antipsychotic drug)?
N O
O
O N O O
H
O O
O
(A) 7 (B) 8 (C) 9 (D) 10
6. The following molecule is fluorometholone, a steroidal anti-inflammatory agent. How many stereogenic centers
does it contain ?
O CH3
H3C
HO OH
H3C
F H fluorometholone
O
CH3
(A) 5 (B) 6 (C) 7 (D) 8
7. Allegra, a common prescription drug with the structure shown below, is given for the treatment of seasonal
allergies. How many stereogenic carbon does allegra possess ?
CH3
COOH
CH3
H N
OH
HO
(A) 4 (B) 2 (C) 3 ( D) 1
8. Choose the correct option for column-I and column-II.

Column-I Column-II
CH3 CH3
(A) C=C (P) Number of stereocenter is even number
H Cl
H
H C
Cl
(B) (Q) Number of stereocenter is odd number
Cl
O
||
(C) CH3–S–CH=CH–CH3 (R) It will show geometrical isomerism
OH H
(D) (S) It will not show geometrical isomerism
HO H
(A) A-Q, R ; B-P,R ; C- Q, R ; D - P, R
(B) A-P, R ; B-Q,R ; C- P, R ; D - Q, R
(C) A-P, R ; B-Q,R ; C- Q, R ; D - P, R
(D) A-P, R ; B-Q,R ; C- Q, S ; D - P, R
One or more than one Type Question
9. Which of the following given compound have odd number of chiral center ?
(A) (B)
(C) (D)
Integer Type Question
10. Calculate sum of total number of chiral centers in given below given compounds.
HO Cl
Cholesterol (a) (b)
11. How many compounds have two chiral center ?
O
O O CH3 OCH3
(I) (II) (III) (IV) O
CH3 CH3
CH3
H3C O CH3 H3C O CH3

(V) (VI)
O O
H3C
12. How many compounds shown below have single chiral center?
OH OH
(I) H (II) III) (IV)
O
O
(V) (VI) (VII) (VIII)

O
O
O
Cl
(IX) (X)
H3C CH3
O Cl
13. How many chiral carbon atoms are present in the following compound ?
O
H3C O CH2 C NH
S
N
O
COOH
Penicillin V
Answer Key + Solution
1. D 2. B 3. C 4. D 5. B
6. D 7. D 8. C
9. C,D
10. 14 11. 3 12. 0 13. 3
Solution
1. D
2. B
3. C
CH3 CH3 CH3 CH3

H H * H H *
*
* CH3 CH3 CH3 CH3
* * * *
H H CH3 CH3
* *
H H
CH3 CH3
(I) = 3 (II) = 4 (III) = 2 (IV) = 3
4. D
minimum 4 carbon
5. B
* N O
O
* *
*
O N * O O
H *
* *
O O
n=8 O
6. D
O CH3
H3C
HO OH
* *
H3C *
* *
* F * H
O *
CH3
7. D
CH3
COOH
CH3
N *
H
OH
HO
8. C
A-P, R ; B-Q,R ; C- Q, R ; D - P, R
CH 3 * CH 3
Sol. (A) * Stereocenter = 2 ; Geometrical Isomer
C=C
H Cl
H
H C
(B) * Cl Stereocenter = 3 ; Geometrical Isomer
*
*
Cl
O
||
(C) CH 3–S–CH=CH–CH 3 Stereocenter = 3 ; Geometrical Isomer
* * *
OH H
*
(D) Stereocenter = 2 ; Geometrical Isomer
HO H
9. C,D
10. 14
* O
* * *
*
Sol. * * *
* * *
HO * * * Cl
Cholesterol (b) = 5
(a) = 9
11. 3
O
O O CH3 OCH3
* *
Sol. (I) (II) (III) (IV) O
*
CH3
* * CH3 *
CH3
H3C O CH3 H3C O CH3
(V) * * (VI) *
O * O
H3C
12. 0
OH OH
*
Sol. (I) H (II) III) (IV) *
* *
O
O *
* * * * *
(V) (VI) * (VII) * (VIII) * *
* * O
O
* * Cl
(IX) (X) *
* * H3C CH3
*
O Cl
13. 3 O
H3C O CH2 C NH
* S
*
N
*
O
Sol. COOH
Penicillin V
n=3
1. Indicate the structure/s having R configuration.
CH2=Cl F CH2–OH
CH=CH2
C C C
(A) C (B) H C (C) HO (D) D
CH2–CH2–Cl CH3 OCH3
H CH3 3
OH NH2 T
COOH
2. The S-enantiomers of ibuprofen is reversible for its pain relieving properties. Which one of the structure
shown is S-ibuprofein?
(A) (B)
(C) (D)
3. Which of the following molecules is achiral ?

(A) (2R, 3R)-2,3-dichloropentane (B) (2R, 3S)-2,3-dichloropentane
(C) (2S, 4S)-2,4-dichloropentane (D) (2S, 4R)-2,4-dichloropentane
4. (R)-2-chlorobutane is represented by :
(I) (II) (III) (IV)
(A) I (B) II (C) III (D) IV
5. Which of the following represent (R)-2-butanol ?
(I) (II) (III) (IV)
(A) III and IV (B) I, III, and IV (C) I and IV (D) I and III
6. Which structure represents (S)-1-chloro-1-fluoroethane ?
(A) I (B) II (C) III (D) More than one of the above
7. Which structure represent (R)-1-chloro-1-fluoroethane ?
(A) I (B) II (C) III (D) More than one of the above
8. Which structure represents (S)-2-bromobutane ?
(A) I (B) II (C) III (D) None of the above
9. is properly named :
(A) (3R, 4S, 5R)-3,5-dichloro-4-methylhexane

(B) (2S, 3S, 4S)-2,4-dichloro-3-methylhexane
(C) (2S, 3R, 4R)-2,4-dichloro-4-methylhexane
(D) (2S, 3R, 4S)-2,4-dichloro-3-methylhexane
10. The Cahn-Ingold-Prelog stereochemical designations used for the following substance are :
(A) 2R, 4S (B) 2S, 4R (C) 2R, 4R (D) 2S, 4S
11. Which of these is not a correct Fischer projection formula of the (S) form of 3-bromo-1,1-dichloro-2-propanol?
CHCl2 CH2Br H OH
H OH HO H Cl2HC CH2Br H CHCl2
CH2Br CHCl2 OH CH2Br
(I) (II) (III) (IV)
(A) I (B) II (C) III (D) IV
12. Indicate figure/s having S configuration.
CH2–CH3
CH2–CH3 SR CH2–CH3
H3C OPh
H3C I
(A) (B) H NR2 (C) (D)
CH3 Et CH2–CH2–CH3
13. Match the column-I with column-II, where column-I indicates a compound and column-II indicates its
configuration. Note that column-I may have more than one matching options in column-II.
Column-I Column-II
(A) (P) 2R 3S
(B) (Q) S
(C) (R) R
(D) (S) 2S 3R
(A) A-Q ; B-R ; C-P ; D - S

(B) A-S ; B-R ; C-P ; D - S
(C) A-R ; B-Q ; C-P ; D - S
(D) A-S ; B-P ; C-R ; D - Q
14. How many compounds having R configuraiton in the following given compounds.
(1) (2) (3) (4)
(5) (6) (7)
1. A 2. B 3. D 4. C 5. C
6. D 7. B 8. A 9. D 10. C
11. D
12. BCD 13. C
14. 4
Solution
1. A
2
CH=CH2
4 C 3 SR
H CH3
1COOH
2. B
3. D
Cl H Cl H
2 4
1 3 5
4. C
4
H
3 1
H3C Cl
2 CH CH3
2
(R-2-Chlorobutane)
5. C
4 4 3
H H CH3
1 1 3 1 4
3
(I) H3C OH (III) HO CH3 (IV) HO H
2 2 2
CH2CH3 CH2CH3 CH2CH3
R-2-butanol S-2-butanol R-2-butanol
6. D
2 2 3
F F CH3
1 4 4 1 4 1
Cl H H Cl H Cl
3 CH3 3 CH3 2F
(I) = S (II) = R (III) = S
7. B
2 2 3
F F CH3
1 4 4 1 4 1
Cl H H Cl H Cl
3 CH3 3 CH3 2F
(I) = S (II) = R (III) = S
8. A
3
CH3
4 1
H Br S
2
CH2CH3
9. D
5 6
CH2CH3
3
4 4 1
H 1
Cl =S
2
4 3
3 (2S, 3R, 4S)-2,4-dichloro-3-methylhexane
H CH3 = R
2
1 2 4
Cl H =S
3
1 CH3
10. C
4
H 3 3
1
Cl
Cl 4 3 2 4 =R
R= 1 2 H (2R, 4R)
5 1 2
Cl
Cl
11. D
1
OH
4 3
H CHCl2
1 CH2Br
(R)
12. BCD
1
SR
4 2
(B) H NR2 =S
3 Et
3
CH2–CH3
4 1
(C) H3C I =S
2
CH2–CH2–CH3
3
CH2–CH3
4 1
(D) H3C OPh =S
2
13. C
A-R ; B-Q ; C-P ; D - S
3
1 4
Sol. (A) NH2 CH = NH =R
2
CH2OH
4 5 1
1 1
(B) 3 6 =S
1
2 1
4
CH3
3
H Cl = S
(C) = 2R–3S
2
H Br = R
1CH3
1
COOH
2
HO H =S
(D) = 2S–3S
3
H OH = R
CH3
4
14. 4
Sol. (1) S (2) R (3) R (4) R (5) no chiral centre (6) S (7) R
1. (+) 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
2. If optical rotation produced by is + 36º then that produced by is
(A) –36º (B) 0º (C) +36º (D) unpredictable
3. 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
4. The racemic mixture of Alanine can be resolved by using,
(1) (+)-2-Butanol (2) ()-2-Chlorobutanoic acid

(3) (±) -2-Butanol (4) (d mix)-2-Chlorobutanoic acid
(A) 1 & 2 only (B) 1 & 3 only (C) 2 & 4 only (D) 3 & 4 only
5. The major 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)
6. 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) CH3  CH  COOH and H2N–CH2–CH2–COOH
|
NH2
(D) (+)-lactic acid and (–)-lactic acid
7. Which of the following amine is optically active ?
(A) CH3NH2 (B) CH3NHC2H5
(C) CH3CH2CH2– (D) sec-Butylamine
8. The following molecules are :

H CH3
C=C=C
H3C H
(A) Enantiomers (B) Diastereomers (C) Identical (D) Conformers
9. Which of the following is/are chiral ?
(A) (B)
H Br
(C) (D)
Br H
10. Which of the following compounds will show optical activity ?
(A) (B) (C) (D)
11. Pure (R) Mandelic acid has specific rotation of –150. If a smaple contains 60% of
the R and 40% of its enantiomer, then [] of this solution is.
Answer Key
1. B 2. B 3. C 4. A 5. A 6. D 7. D
8. A 9. CD 10. CD 11. 30
1. Which is not the pair of enantiomers ?
(A) (B)
(C) (D)
2. Which of the following pairs of compounds are enantiomers :
CH3 CH3 CH3 CH3
OH and HO H H OH HO H
(A) H (B) HO and
OH H H OH H HO H
CH3 CH3 CH3 CH3
CH3 CH3 CH3

H OH HO H HO H
(C) and OH
(D) H OH and HO H
H
CH3 CH3 CH3
3. Stereoisomers which are not mirror image of each other, are called :
(A) Enantiomers (B) Tautomers (C) Meso (D) Diastereomers
4. How is each molecule (I-IV) related to compound A ?
(i) (ii)
(iii) (iv)
(A) (i) Constitutional isomer, (ii) stereoisomer, (iii) identical, (iv) stereoisomer
(B) (i) Stereoisomer, (ii) Constitutional isomer, (iii) identical, (iv) stereoisomer
(C) (i) Identical, (ii) Constitutional isomer, (iii) identical, (iv) stereoisomer
(D) (i) Stereoisomer, (ii) Identical, (iii) Constitutional isomer, (iv) identical
5. Which of the following pair of molecules represents pair of enantiomers ?
(A) (B)
(C) (D)
6. Consider the newman projection formulas shown below :
(A) (B) (C)
Which of the following statements is the correct ?

(A) Compound (A) and (B) are enantiomers.
(B) Compounds (A) and (C) are identical.
(C) Compounds (B) and (C) are enantiomers.
(D) Compounds (A), (B) and (C) are optically active.
7. Which of the following pair is enantiomer ?
(A)
(B) and
(C)
(D)
8. Find the number of enantiomers possible for Cl–CH=C=CH–Cl

(A) 4 (B) 2 (C) Zero (D) 1
9. (i) (ii)
(iii) (iv)
Which are identical pair?

(A) (I), (II) (B) (II), (III) (C) (III), (IV) (D) (I), (IV)
10. A pair of stereoisomers might be classified in various ways. Which of the following statement are
true with respect to pairs of stereoisomers ?
(a) They might be configurational isomers (b) They might be diastereomers
(c) They might be constitutional isomers (d) They might be tautomers
(e) They might be conformational isomers (f) They might be enantiomers
(g) They might be positional isomers
(A) a, b, c, e (B) b, d, e, f, g (C) a, b, f (D) a, b, c, f
11. Which of the following is an enantiomer of D-glucose.
(A) (B)
(C) (D)
12. Which of the following depict the same stereoisomer ?
(I) (II) (III)
(A) I and II (B) I and III (C) II and III (D) I, II and III
13. Which pairs of the salts should have identical solubilities in methanol ?
(I) (II)
(III) (IV)
(A) I & IV (B) I & III (C) I & II (D) II & IV
14. Which of the following pair of molecules represents pair of enantiomers ?
(A)
(B)
(C)
(D)
15. Calculate total number of enantiomeric pairs among given structures

F I
H T
(i) (ii) I F
T H Cl Cl
Cl Cl Br Br
D D
H F CH=CH2 D
(iii) T D H D (iv) D F Cl F
F T Cl CH=CH2
Me Et
H H
H OH H OH
HO F F OH
(v) (vi) HO H HO H
Cl OH HO Cl
Et Me
D D
Cl Cl
(vii)
Br Br
Answer Key
1. D 2. A 3. D 4. C 5. C 6. C 7. B
8. B 9. D 10. C 11. A 12. D 13. A 14. AB
15. 3
1. Which of the following is/are D-carbohydrate ?
(A) (B) (C) (D)
2.
(D) & (L) configuration of above carbohydrate is :

(A) L, L, D (B) L, D, L (C) L, L, L (D) L, D, D
3. Which of the following molecules is expected to rotate the plane of polarised light?
(A) (B) (C) (D)
4.
Correct statement for above compound is :

(A) I, II & III have D-configuration.
(B) I, II have D-configuration.
(C) I, II have L-configuration.
(D) II & III are enantiomers of each other.
5. In D-glucose 'D' represents :

(A) dextrorotatory (B) its configuration
(C) its diamagnetic nature (D) dipole moment
6.
Correct statement for compounds :

(A) I & II are enantiomers of each other.
(B) I having D-configuration and II having L-configuration.
(C) I & II are C5 - epimer of each other.
(D) B & C both are correct.
7. Which of the following given compounds show amine flipping :
(A) (B) (C) (D)
8. Which of the following given compounds are resolvable :
(A) (B)
(C) (D)
9. -D-glucose and -D glucose are :

(A) Enantiomers (B) Geometrical isomers
(C) Epimers (D) Anomers
10.
Above compound are epimer due to change in configuration at one chiral centre. Identify correct option for I & II.
(A) C2-epimer (B) C3-epimer (C) C4-epimer (D) Not epimers
1. D 2. B 3. C 4. B 5. B
6. D 7. C 8. D 9. D
10. B
Solution
1. D
(A) (B)
(C) (*D)
2. B
3. C
 Optically active
4. B
In fisher more than one chiral center are present then D & L decided by lowest chiral centre if –OH group on
this chiral center is at left then L otherwise D.
5. B
'D' represents configuration.
6. D
C5-epimer of each other.
7. C
For amine flipping central atom should be of 2nd period and contains at least one l.p. on it and central atom
should not be the part of ring formation & l.p. does not undergo resonance.
8. D
Compound which are resolvable are optically active, does not contain POS & COS.
9. D
(only change at chiral centre 1  cyclic epimers are anomers)
10. B
Cl Cl Cl Cl
1.
Br Br Br Br
(A) (B)
Relationship between above pair (A) & (B) is :
(A) Enantiomer (B) Diastereomers (C) Identical (D) Structural isomer
2. Relation between x and y is :
(A) Enantiomers (B) Diastereomers (C) Position isomer (D) Identical
(A) Enantiomers (B) Diastereomers (C) Position isomer (D) Identical
(A) Enantiomers (B) Diastereomers (C) Different compound (D) Identical
5. Relation between given compound is :
(A) Distereomer (B) Structural isomer (C) Enantiomer (D) Identical

6. Identify which is diastereomer
Cl Cl
(A) &
Br Br
(B) &
(C) &
O O
&
(D) O O
7.
(I) (II) (III) (IV)
Correct statement regarding above given compounds is

(A) I and II are diastereomers (B) I and III are identical
(C) III and IV are identical (D) I and II are conformers
CH3 CH3
8. Cl H Br H
H Br H Cl
CH3 CH3
(I) (II)
Compound I and II are

(A) Identical (B) Position Isomer (C) Enantiomers (D) Diastereomers
9. Which of the structures is/are diastereomer of A?
(A)
O
(1) (2) (3) (4) (5)
|| O || ||
O O O
(A) 3 (B) 1 and 4 (C) 2 and 3 (D) 5
10. Which of the following cyclohexane derivatives is most stable ?
(I) (II) (III) (IV)

(A) (I) (B) (II) (C) (III) (D) (IV)
11. (2R, 4S)-2, 4-dichloropentane and (2S, 4R)-2, 4-dichloropentane are :

(A) Enantiomers (B) Diastereomers (C) Identical (D) Conformational isomers
12.
H
(a) (b)
Correct relationship in between a & b

(A) Diastereo isomer (B) Enantiomeric (C) Geometrical isomers (D) Structural Isomers
13. Choose correct relationships of given below structure among all options.
(P) C=O (Q) C=O

H H
(R) C=O (S) C=O
H H
(A) (P,Q) Diastereoisomer (B) (Q,R) Diasteromer
(C) (P,S) Enantiomers (D) (Q,S) Diasteromer
14. Find out the compound in which all the atoms lies in same plane (in all conformations).
C CH
CN H H
(A) (B) C=C=C=C
H H
CN
Cl CH3
(C) C=C (D) CH3–CN
Br D
15. Identify which are configurational (optical or geometrical) isomer.
(A) & (B) &
&
(C) Br Br Br (D)
Br Br Br Br
Br
16. Numerical value of difference between number of enantiomeric pairs and diastereo isomers
Cl Cl
D D
(i) (ii)
T T
Br Br
OH Et Me
H OH H OH
(iii) (iv)
Cl H Cl H
OH Me Et
OH CH3
H OH
(v) H
Match The Column Type Question :
17. Column-I Column-II

HO H
(A) H3C CH3 H3C CH3 (P) Identical
H OH
H
H H
H3C H
(B) (Q) Enantiomer
H H H H
CH3 CH3
CH3
CH3 CH3
H H H H
(C) H H H CH3 (R) Diastereomer
CH3 H
Cl OH
H Cl H Cl
(D) (S) Constitutional isomer

HO H Cl H
OH OH
(A) AS; BP; CR; DR
(B) AS; BQ; CS; DR
(C) AS; BP; CS; DQ
(D) AS; BP; CS; DR
1. A 2. B 3. B 4. A 5. D
6. C 7. D 8. A 9. B 10. A
11. C
12. AC 13. ABCD 14. AB 15. BCD
16. 2
Match the column
17. D
Solution
1. A
Cl Cl Cl Cl
Sol.
Br Br Br Br
(A) (B)
Non-super imposeble mirror image.
2. B
3 3
CH3 CH3
4 1 1 4
H Br = S Br H =R
2 2
1
H 3
Cl = R H Cl =R
1 3 1
CH3 CH3
(x) (y)
Both are diastereomers of each other.
3. B
down
up
cis
trans
Both are diastereomers of each other.
4. A
Enantiomers of each other.
5. D
6. C
&
Sol.
Trans Cis
Cis and trans are diastereomer
7. D
T
Sol. T
T
T
8. A (I) (II)
4 1
CH3 CH3
2
R Cl 3
H Br H R
Sol. 3
R H 2
Br H Cl R
4
1
CH3 CH3
(I) (II)
both are identical
(2R-3R)
2-Bromo-3-chloro butane
9. B
4
H O H
3 1 2S 4S O
4H 2
H 2S
2 1
21 2 H
Sol. 2
3 1 4S
3 4S 2S 3 1||
H O
(A)
10. A
Sol. Bulky groups are more stable on equatorial position.
5 1 5
6 6 1
3 > 3
4 2 4 2
11. C
Cl H Cl H Cl H Cl H
2 4 2 4
1 3 5 1 3 5
2S–4R 2R–4S
One or more than one Type Question :

12. AC
Sol.
H
Cis Trans
Cis, trans are diastereoisomer

Cis, trans are geometrical isomer
13. ABCD
C=O O=C
H H
(P) (S)
Both are non-super imposeble mirror image of each other.
Other then these all are diastereoisomer.
14. AB
3
sp
H H Cl CH3
Sol. (B) C=C=C=C (C) C=C (D) CH3–CN
H H Br D sp
3
same plane
15. BCD
Sol. (A) &  Conformer
(B) &  Geometrical Isomer
(C) Br Br Br  Optical Isomer
Br
&
(D)  Optical Isomer
Br Br Br Br
16. 2
Cl Cl
D D
Sol. (i) (ii)
T T
Br Br
Diastereomer Diastereomer
OH Et Me
H OH H OH
(iii) (iv)
Cl H Cl H
OH Me Et
Enantiomer 2-Chloro pentan-3-ol 3-Chloro pentan-3-ol
OH CH3
H OH
(v) H Diastereomer
Cis Trans
17. D
AS; BP; CS; DR
HO H
4 4 2
2 5 3 1
Sol. (A) H3C CH3 H3C CH3 (Structural isomer)
3
1 5 H OH
H
H H
H3C H
(B) (Identical)
H H H H
CH3 CH3
CH3
CH3 CH3
CH3–CH CH3–CH
CH3 CH3
CH3 CH3
H H H H
(C) Constitutional isomer

H H H CH3
CH3 H
H3C
CH3–CH2–CH2–CH3 CH–CH3
H3C
Cl OH
H Cl H Cl
(D) Diastereomer
HO H Cl H
OH OH
OH OH
H Cl H Cl
Cl H H Cl
OH OH
1. Which of the following compounds have only one POS ?
Cl
CH3
Cl H Br O
(I) (II) H (III) O (IV)

Br
Cl CH3
Cl
(A) I, IV (B) I, II, IV (C) II, III (D) I, II
2. Identify the compounds having/possess molecular POS ?
CH3 CH3
H3C CH3 H H
(I) C=C (II) (III) (IV) C=C=C
H H CH3 Cl H
CH3
(A) I, II (B) I, II, III (C) II, III (D) All
3. Number of compound possess plane of symmetry ?
CH3 H OH
CH3 H
H Br H H
CH3
(a) Br H (b) (c) (d)
D D
CH3 D H H
D
OH
H H
H H H
H H
H
(e) C=C=C (f) H–C (g)
C–H
Br Br Cl
H H Cl
(A) 4 (B) 5 (C) 6 (D) 7
4. Identify compounds have plane of symmetry ?
O O
(I) (II) (III) (IV) (V)
O O
(A) II, V (B) I, IV, V (C) I, III, IV (D) IV, V
5. Identify that compounds which have plane of symmetry
D Br
H OH H H
(I) (II) (III) C=C=C
HO H H H
Br Br
D
CH3
H Br
(IV) BF3 , (V) H Br
CH3
(A) II only (B) II, IV, V (C) II, IV (D) II, III, IV, V
6. Number of isomers of C7H14 (having cyclopentane ring) which have plane of symmetry.
(A) 3 (B) 4 (C) 5 (D) 6
7. Maximum number of plane of symmetry possible in
Cl
Cl Cl Cl
Cl
(A) (B) (C) (D)
Cl
Cl
8. Which molecule has plane of symmetry present (In given conformation)?
COOH COOH
CH3 CH3 O
H OH H OH O
(A) H OH (B) HO H (C) (D) O
H
COOH COOH Br Br H O
9. Which compound does not possess a plane of symmetry?
Br Br CH3
Cl H
H Br O
(A) (B) Br H (C) (D) O
H Br
FF
CH3 H CH3
10. In which of the following compound plane of symmetry are present.
(A)
11. Number of compound having POS is x then compute (x + 2) ?
Cl Cl
Cl Cl
Br Br
D F
Compound : , , , ,
D Br Br
F
Cl Cl
Cl Cl
1. D 2. D 3. B 4. D 5. D
6. B 7. B 8. A 9. A 10. ABC
11. 2
Solution
1. D
CH3
Cl
H Br
(I) (II) (III) (IV) (4 POS)
H Br
Cl CH3
2. D
H H
H3C CH3 C=C=C
(I) C=C (II) (III) (IV) Cl H
H H
3. B
b, c, d, f, g
4. D
5. D
C2
Br C3
C3
F
(II) (IV) F B
Br Br F
6. B
7. B
(A) : 2-POS (i) Vertical (ii) molecular plane
(*B) : 3-POS (i) Vertical (ii) Molecular plane (iii) Horizontal
(C) : 2-POS (i) Molecular plane (ii) diagonal
(D) : 2-POS (i) Molecular plane (ii) Diagonal
8. A
9. A
Br Br
FF
Does not have plane of symmetry because
10. ABC
POS
(A) 
Cl
(B) 
Cl
CH3 CH3
(C) 
H Br H Br
O
Cl
O
(D) O ×
Cl
O
11. 5
Cl Cl
Cl Cl
Br Br
D F
D Br Br
F
Cl Cl
Cl Cl
POS     
x=3
x+2=5
1. Which of the following compounds have centre of symmetry ?
Cl
CH3
Cl H Br O
(I) (II) H (III) O (IV)

Br
Cl CH3
Cl
(A) I, IV (B) I, II, IV (C) II, III (D) None of these

2. Identify the compounds possess centre of symmetry ?
CH3
H3C CH3
(I) C=C (II) (III) (IV)
H H CH3 CH3
(A) II, IV (B) I, II, III (C) II, III, IV (D) Only II
3. Number of compound possess centre of symmetry (in given form) ?
CH3 H OH
CH3 H
H Br H H
CH3
(a) Br H (b) (c) (d)
D D
CH3 D H H
D
OH
H H
H H H
H H
H
(e) C=C=C (f) H–C (g)
C–H
Br Br Cl
H H Cl
(A) 0 (B) 1 (C) 2 (D) 3
4. Identify compounds have centre of symmetry (Ci) ?
O O
(I) (II) (III) (IV) (V)
O O
(A) II, V (B) I, IV, V (C) I, III, IV (D) All
5. Which of the following is correct for the given compound.
(A) It posses center of symmetry (B) POS is present but COS absent
(C) It posses plane of symmetry (D) B and C both are correct
6. Number of isomers of C7H14 (having cyclopentane ring) which have centre of symmetry.
(A) 0 (B) 1 (C) 2 (D) 3
7. Identify the compound in which COS is present
Cl
Cl Cl Cl
Cl
(A) (B) (C) (D)
Cl
Cl
8. Which molecule has centre of symmetry present (in any possible stable conformation) ?
COOH COOH O
H OH H OH CH3 CH3 O
(A) H OH (B) HO H (C) (D) O
H
COOH COOH Br Br H O
9. Symmeteries present in the given compound.
(A) Plane of symmetry (POS) (B) Centre of symmetry (COS)

(C) Both A and B is correct (D) neither POS nor COS is present
10. In which of the following compound plane of symmetry and centre of symmetry both are present.
O
Cl Cl
CH3 CH3 O
(A) (B) (C) (D) O
Cl H Br H Br Cl
O
11. Number of compound having COS & POS both ?
Cl Cl
Cl Cl
Br Br
D F
Compound : , , , ,
D Br Br
F
Cl Cl
Cl Cl
1. D 2. D 3. B 4. A 5. D
6. A 7. B 8. A 9. C 10. B
11. 2
Solution
1. D
2. D
3. B
Only d
4. A
O
(II)
*
O
(V) *
5. D
6. A
7. B
8. A
9. C
10. B
POS COS
(A)  ×
Cl
(B)  
Cl
CH3 CH3
(C)  ×
H Br H Br
O
Cl
O
(D) O × 
Cl
O
11. 2
Cl Cl
Cl Cl
Br Br
D F
D Br Br
F
Cl Cl
Cl Cl
POS     
COS     
1. Which of the following compounds have C2 axis of symmetry only ?
Cl
CH3
Cl
H Br O
(I) (II) (III) (IV)
H Br O
Cl
CH3
Cl
(A) I, IV (B) I, II, IV (C) II, III (D) III, IV
2. Identify that compounds which have both C2 as well as C3.
D Br
H OH H H
(I) (II) (III) C=C=C
HO H H H
Br Br
D
CH3
H Br
(IV) BF3 , (V) H Br
CH3
(A) II only (B) II, IV, V (C) II, IV (D) None of these
3. Which of the following is correct for the given compound.
(A) It posses center of symmetry (B) It posses C3 axis of symmetry

(C) It posses plane of symmetry (D) B and C both are correct
4. Symmeteries present in the given compound.
(A) Plane of symmetry (POS) (B) Centre of symmetry (COS)

(C) C2 fold axis of symmetry (D) C3 axis of symmetry
CH3
H Cl
(P) (1) Centre of symmetry
H Cl
CH3
Cl
(Q) (2) C2 axis of symmetry

Cl
Cl Br
(R) (3) Plane of symmetry
Br Cl
CH3
(S) H Cl (4) Compound shows optical isomerism
Cl H
CH3
Codes :
P Q R S
(A) 3 4 1 2
(B) 3 2 1 4
(C) 4 1 2 3
(D) 4 2 1 3
6. (A) (P) Compound posses plane of symmetry

N
Br
CH3
(B) C (Q) Compound possess centre of symmetry
CH3
CH3
CH3
(C) (R) Compound having C2 axis of symmetry

CH3
Br
Br Br
(D) (S) Compound having C3 axis of symmetry

Br Br
Br
(A) C2-axis of symmetry (P)
(B) C3-axis of symmetry (Q)
H3C
(C) Plane of symmetry (R)

CH3
H3C
(D) Centre of symmetry (S)
H3C
(T)
CH3
(A) (P) Centre of symmetry
Cl
(B) (Q) C2 axis of symmetry

Cl
Cl Br
(C) (R) Plane of symmetry
Br Cl
CH3
(D) H Cl (S) Optically active
Cl H
CH3
(T) C3 axis of symmetry
9. Number of compound having C2 is = ?

Compound
H H D
H
D H D H D T H D T T D D
H
, , , ,
T T T D H T H D D T T
T
H
10. How many given compound have two fold axis of symmetry (C2)
H Br Cl
O
, CH4, , , CH3Cl, , CH2Cl2

Br Cl Cl
H
1. D 2. C 3. D 4. ABCD 5. A
6. A-P,R ; B-P,S ; C-R ; D-R,Q,R,S
7. A-P,Q,S,T ; B-P,R ; C-P,Q,R,S,T ; D-P
8. A-P,Q,R,T ; B-R ; C-P ; D-Q,S
9. 2
10. 6
Solution
1. D
CH3
Cl
H Br
(I) (II) (III) (IV) (4 POS)
H Br
Cl CH3
2. C
C2
Br C3
C3
F
(II) (IV) F B
Br Br F
3. D
4. ABCD C2
C3
*
POS
5.
(P)
Cl
(Q) This compound has chiral centre and POS

Cl
Hence is optically inactive but will show optical isomerism.
(R)
(S)
Hence C2 axis of symmetry.
1. Find the alternate axis of symmetry present in given molecule
(A) S2 (B) S3 (C) S4 (D) S6
2. Which of the following does not contain alternate axis of symmetry
(A) (B) (C) (D) All of these
3. Which of the following given compound have alternate axis of symmetry
(A) (B) (C) (D)
4. If methane (CH4) molecule is placed in a cube (as given in diagram) then find the alternate axis of symmetry
H
H
(A) S6 (B) S4 (C) S2 (D) S1
Answer Key
1. A 2. B 3. D 4. BD
1. Identify the compounds which are chiral as well as optically active and also count number of chiral center.
H CO2H H OH H CO2H
(I) , (II) , (III)

HO CO2H OH CO2H H OH
(A) I, II, III and 2, 2, 2 (B) I, III and 2, 2, 2 (C) I, II, III and 2, 0, 2 (D) I, III and 2, 0, 2
2. Ignoring specific markings, which of the following objects are chiral ?

(I) a shoe (II) a book (III) a pencil
(IV) a pair of shoes (consider the pair as one object)
(V) a pair of scissors
(A) I only (B) I & V (C) I, IV, V (D) III, IV, V
3. Which of the following compound is achiral ?
CH2 CH2 CH2 CH2
(A) (B)
CH2 CH2 CH2 CH2
CO2H CO2H
CH2 CH2
CO2H
(C) (D)
CH2 CH2
CO2H
4. Which conformer of butane are chiral in the given form
CH3 H
H CH3 HH HH HH
H H H H
(1) (2) (3) (4)

H H H CH3
H CH3
CH3 CH3 CH3
CH3
(A) 1, 2 (B) 2, 3 (C) 2, 4 (D) 1, 3

5. Identify the correct statement regarding given compounds.
(I) , (II)
(A) Compound I is chiral, optically active and having number of C.C. = 2.

(B) Compound II is chiral, optically active and having number of C.C. = 2.
(C) Compound II is achiral, optically inactive and having number of C.C. = 2.
(D) Compound I & II both are identical.
6. How many compounds shown below are chiral ?
O O
O Cl
CH3 CH3
O
O O Cl
(VI) (VII) (VIII) (IX) (X)
(A) 4 (B) 5 (C) 6 (D) 8
7. Correct statement/s regarding compounds.
CH2–OH Me
Cl
Cl H Cl
(I) H , (II) , (III) , (IV) , (V) H
H Cl
CH2–OH
Me
(A) All are optically active and chiral molecule.

(B) Number of chiral centre is exactly same in all molecules.
(C) Only I is chiral and optically active.
(D) All are optically inactive and achiral molecule.
8. Identify the correct statement
(A) Number of stereoisomers of 2, 3 dichlorobutane are 3
CH3 CH3
Me Me
(B) & are not geometrical isomers of each other
H H
F Cl
(C) C=C have no symmetry
I Br
Cl
Cl Cl
(D) does not show position isomerism
Cl Cl
9. Choose the correct option for column-I and column-II.

Column-I Column-II
(A) (P) Centre of symmetry
Cl
(B) (Q) C2 axis of symmetry

Cl
Cl Br
(C) (R) Plane of symmetry
Br Cl
CH3
(D) H Cl (S) Optically active
Cl H
CH3
(T) C3 axis of symmetry

(A) A - P, Q, R, T ; B - R ; C - P ; D - Q, S
(B) A - P, Q, R ; B - Q, R ; C - P ; D - Q, S
(C) A - P, Q, R ; B - R ; C - P, R ; D - Q, S
(D) A - P, Q, R ; B - R ; C - P ; D - P, Q, S
Match The Column Type Question :
10. Choose the correct option for column-I, column-II and column-III.
Column-I Column-II Column-III
(Compound) (Number of stereocentre)
(A) (P) Optical active (W) 0
(B) (Q) Optically inactive (X) 1
(C) (R) Plane of symmetry (Y) 2
(D) (S) Centre of symmetry (Z) 3
(A) A-PY ; B - QRY ; C - PX ; D-QRY

(B) A-PZ ; B - QRY ; C - PX ; D-QRY
(C) A-PY ; B - RY ; C - PX ; D-QRY
(D) A-PZ ; B - QRY ; C - PX ; D-QRW
11. Calculate total number of chiral compounds?
OH NH2 O
CN
(a) (b) (c) (d)
CO2H OH
NO2
CO2H CN OH SO3H
H OH H OH
(e) H OH (f) HO CH3 (g) CH3 (h)
CH2–CO2H CH2–CO2H NO2
SO3H
CH3 CH3 CH3
C=C=C H Cl
(i) (j)
H H H Cl
CH3
1. B 2. B 3. C 4. B 5. B
6. A
7. BC 8. ABD 9. A
Match the column
10. B
11. 6
Solution
1. B
(II)
• C.C. = 2
• POS present
• Achiral
• Optically inactive
(III)
• C.C = 2
2. B
(I) (II) (III)
(iv) (v)
3. C
CH2 CH2
CO2H
CH2 CH2
CO2H
POS is present  Achiral
4. B
(1) Vertical POS (4) Vertical and molecular POS
5. B
(I) COS is present
(II)
• C.C = 2
• No symmtery element
• Chiral optically active
6. A
Compound which are chiral are (II), (V), (IX), (X)
7. BC
(I) , (II) , (III) , (IV) , (V)
• No ; POS
• No COS
• Chiral
• Optically active
8. ABD
(A)  RR ; RS or SR ; SS
CH3 CH3
Me Me
(B) &
H H
Are not geometrical isomer as aerial distance does not change.
F Cl
(C) C=C ; Have molecular plane of symmetry..
I Br
Cl
Cl Cl
(D) Yes, does not show position isomer..
Cl Cl
9. A
A - P, Q, R, T ; B - R ; C - P ; D - Q, S
(A) Molecule posses C.O.S. with centre z
(B) P.O.S.
(C) C.O.S. present
(D) Optically active
10. B
A-PZ ; B - QRY ; C - PX ; D-QRY
Sol. (A)
No POS & COS

S.C. =3
(B)
Optically inactive
S.C. = 2
(C)
No POS & COS

S.C. = 1
(D)
Optically inactive
S.C. = 2
11. 6
CO2H
OH NH2 O H OH
CN
Sol. (a) (b) (c) (e) H OH
CO2H
CH2–CO2H
CN OH
H OH
(f) HO CH3 (g) CH3
CH2–CO2H
Chiral compound  No symmetry element
1. Which of the following compound is meso compound ?
(A) (B) (C) (D)
2. Which among the following compound is meso compound ?
Cl
Cl
(A) (B) (C) (D)
Cl
3. Which of the following symmetry(s) are present in any conformer of meso tarteric acid ?
(A) POS (Plane of symmetry)
(B) COS (Centre of symmetry)
(C) AAOS (Alternate axis of symmetry)
(D) All
4. Cis-1,2-dichloro cyclohexane is optically inactive due to

(A) Plane of symmetry
(B) Internal compensation
(C) External compensation
(D) All
5. Which of the following pair represent pair of diastereomers?

(A) Meso tartaric acid and () tartaric acid
(B)
(C) and
(D) All of these
6. Identify which of the structures below are meso structures:
(1) (2) (3) (4) (5)
(A) 1 and 3 (B) 1,3 and 5 (C) 1,3 and 4 (D) 2 and 5
7. How many compounds have odd number meso form
(A) (B) (C) (D)
8. Most stable form of meso-2,3-diflouro-2,3-butandiol is:
(A) (B) (C) (D)
9. Which form of given compound is more stable
(A) Meso (B) Optically active (C) Both (D) None
10. Which of the following compound is/are meso compound ?
O
O CH3
H Br
(A) (B) (C) (D) HO OH
O H Br
O OH3
11. Which of the following statement/s are correct for given compounds.
(I) (II)
(A) II has one isomer meso.

(B) Total stereoisomers in both equals to active isomers.
(C) Total stereoisomers for II compound is odd.
(D) Both compounds has plane of symmetry.
12. Which of the following compound has a stereoisomer that is a meso compound
(A) (B)
(C) (D)
Answer Key
1. B 2. A 3. D 4. C 5. D 6. A 7. D
8. C 9. A 10. ABC 11. AC 12. ABC
1. How many optically active isomers are possible for given compound
(A) 0 (B) 1 (C) 2 (D) 3
2. Total number of meso are possible for given compound.

2,4-dichloropentane
(A) 0 (B) 1 (C) 2 (D) 3
3. If total number of optically active isomers for given compound = x

and total number of meso for given compound = y.
Find (x + y)
Cl Cl
Cl Cl
(A) 3 (B) 4 (C) 7 (D) 9
4. Number of optically active isomers and meso for given compound are
(A) 2, 2 (B) 2, 1 (C) 4, 2 (D) 4, 0
5. Number of optically active of following respectively are
OH
(1) (2)
OH
OH
OH OH
(3)
OH
(A) 1, 2, 3 (B) 2, 3, 2 (C) 2, 3, 3 (D) 2, 2, 2
6. Total number of optically active dichlorides of given compound
CH2
(A) 2 (B) 4 (C) 6 (D) 8
7.
Number of meso-isomer are :

(A) 1 (B) 2 (C) 3 (D) 4
8. Find the number of optical active isomer of given compound :
(A) 3 (B) 2 (C) 6 (D) 0
9. Identify alkene showing both geometrical as well as optical isomerism :
(A) (B) (C) (D)
10. Number of optically active isomer is/are :
(A) 0 (B) 1 (C) 2 (D) 3
11. Number of optically active tartaric acid is/are possible :

(A) 1 (B) 2 (C) 3 (D) 4
12. Column I Column II
CH3
H Cl
(A) Cl H (P) Total number of optically active isomers are even
CH3
Cl
(B) (Q) Total number of optically active isomers are odd

Cl
Cl
(C) (R) Total number of meso are zero

Br
(D) CH3–CH=C=CH–CH=CH–CH3 (S) Total number of meso are odd
(A) A-Q,S ; B-P,S ; C-P,R ; D-P,R

(B) A-P,S ; B-Q,S ; C-P,R ; D-P,R
(C) A-P,S ; B-P,S ; C-P,R ; D-P,R
(D) A-P,S ; B-P,S ; C-P,S ; D-P,R
13. Which of the following are optically active?
Me
Me
(A) (B)
Cl
Me Me
H
Me
Me
(C) (D)
Me
Cl
H
14. Which of the following have even number of optically active isomers.
(A) (B) CH3 – CH=C = CH–CH3
F CH3
Cl Br H Cl
(C) (D)
H Br
I
CH3
15. Number of chiral center is x and number of optically acitve isomers is y calculate y – x.
O
1. A 2. B 3. C 4. B 5. D
6. C 7. C 8. D 9. C 10. A
11. B 12. C
13. AD 14. ABCD
15. 6
Solution
1. A
2. B
3. C
x = 4, y = 3
4. B
5. D
OH OH OH
(1) (2) (3)

OH OH
OH
2n = 21 = 2 2n–1 = 22–1 = 2 2n – 2(n–1)/2 = 23–1 – 2(3–1)/2 = 4 – 2 = 2
6. C
7. C
Sol. POS 
POS 
POS 
Three meso are possible.
8. D
Sol.
 COS (1)
All are optically inactive
9. C
Sol. (A) (B) (C) (D)
(* = Chiral centre)
10. A
Sol. , ,
All are optically inactive
11. B
Sol.
2-optically active
12. C
A-P,S ; B-P,S ; C-P,R ; D-P,R
CH3
H Cl
(A) Cl (Optically active isomers = 2, meso = 1)
H
CH3
Cl
(B) (Optically active isomers = 2, meso = 1)

Cl
Cl
(C) (Optically active isomers = 8, meso = 0)

Br
(D) CH3–CH=C=CH–CH=CH–CH3 (Optically active isomers = 4, meso = 0)
13. AD
14. ABCD
15. 6
Sol. Number of chiral center = 2.
Number of optically active isomers = 8
Br
1.
Cl OH
Total number of stereoisomers in the above compound is
(A) 6 (B) 4 (C) 8 (D) 16
2. For the given compound which of the following statement(s) are correct?
D D D
(A) It has 4 stereoisomers (B) It has 3 stereoisomers
(C) It has 2 chiral centres (D) The compound does not show G.I.
3. A naturally occurring substance has the conslilution shown below. How many may have this constitution?
O
HO CH2OH
HO CH CH CH CH CH2 CH2 CH3
(A) 2 (B) 8 (C) 15 (D) 64
4. H3C CH CH CH CH3
Br Br Br
Total number of stereoisomers in the above compound is
(A) 6 (B) 4 (C) 8 (D) 16
5. Total number of stereoisomers of the compound is given below

H3C CH CH CH3
OH Br
(A) 2 (B) 4 (C) 6 (D) 8
6. The number of stereoisomers possibel for the below compund (do not change cis/trans configuration of
olefins) are
CH3
CH3
HO
OH
(A) 8 (B) 16 (C) 32 (D) 12
7. Total number of stereoisomers possible for the given compound is
H3C CH CH CH CH CH3
Br Cl
(A) 2 (B) 4 (C) 8 (D) 16
8. Number of diastereomer of given compound is
CH3
H Cl
H Cl
H Cl
CH3
(A) 2 (B) 3 (C) 4 (D) 5
9. How many meso stereoisomers exist for 2, 3, 4, 5-tetra chloro hexane?

(A) 2 (B) 3 (C) 4 (D) 5
10. The number of stereoisomers possible for a compound of the molecular formula
CH3–CH=CH–CH(OH)–Me is
(A) 2 (B) 4 (C) 6 (D) 3
11. Number of stereoisomers of
H3C CH3
COOH
(A) 2 (B) 3 (C) 4 (D) 5
12. How many diastereoisomers of compound 1 are there?
Me Me
COOH
(A) 1 (B) 2 (C) 3 (D) 4
13. Total number of stereoisomer is odd number for
CHO
COOH Br
H OH
H OH H OH
(A) (B) (C) (D) H OH
H OH H OH
H OH
COOH COOH
COOH
14. Identify which compound is/are having even number of stereoisomer
O O
C C C C
(A) (B)
O O
Br
Cl
(C) (D)
Cl Cl
1. C 2. A 3. D 4. B 5. B
6. B 7. C 8. B 9. A 10. B
11. C 12. C
13. AB 14. ACD
Solution
1. C
Br
* * *
Cl OH
Unsymmetrical compound = 2n
n=3
Total stereoisomers = 23 = 8
2. A
C R T

T R C
* * 
* T S C
C S T
D D D
3. D
TSI = 26 = 64
4. B
R R S
* * * 
H3C CH CH CH CH3 S R R

S S R
Br Br Br R S S
5. B
* *
H3C CH CH CH3
OH Br
R R
 
R S
S S
 
S R
Unsymmetrical n = 2
Total stereoisomer = 2n = 22
Total stereoisomer = 4
6. B
*
CH3
* * * CH3
HO
OH
Total stereoisomer = 2n
n=4
Total stereoisomer = 24 = 16
7. C
* * *
H3C CH CH CH CH CH3
Br Cl
n=3
Total stereoisomer = 2n = 23
Total stereoisomer = 8
8. B
CH3 CH3 CH3 CH3

H Cl Cl H H Cl Cl H
H Cl Cl H H Cl H Cl
H Cl H Cl Cl H Cl H
CH3 CH3 CH3 CH3
Total 3 diasteromers
9. A
Cl Cl Cl Cl
Cl Cl Cl Cl
10. B
n=3
Total stereoisomer = 2n
Totalstereoisomer = 22 = 4
11. C
H3C CH3 H3C CH3 H3C CH3 H3C CH3 H3C CH3
COOH COOH COOH COOH COOH
12. C
Me Me Me Me Me Me
COOH COOH COOH
13. AB
14. ACD
1. Calculate the total number of stereoisomers when alkene having trans configuration :
(A) 2 (B) 3 (C) 4 (D) 8
CH3
2. Number of diastereomers possible for

CH–CH3
(A) 1 (B) 2 (C) 4 (D) 0
Comprehension-1 (Q.3 to Q.4)

Absence of either plane of symmetry or center of symmetry is the necessary and sufficient
condition to show optical isomerism. Compound which will rotated the plane polarised light in
clock wise direction is known as daextro form. It is purely an experimental phemomena, we can’t
predict the daextro or laevo form of compound theoretically
3. Total number of structural as well as stereoisomers possible from molecular formula C7H14 having
cyclopentane ring are
(A) 6 (B) 7 (C) 8 (D) 9
4. How many compounds among the following have a stereoisomer that is Meso?
Br
Cl
Cl
Cl Br
Br Br
Cl Br
(A) 2 (B) 3 (C) 4 (D) 5
5. Total number of stereoisomer
CH3 Br H
CH CH CH CH CH3
H3C
CH3 CH C CH CH3
CH CH2
6. How many stereo isomers are possible for C7 H 8O (only alcohol).
7. Total number of isomers of C6H12 having cyclobutane ring.
8. If molecule is pyramidal, X stereoisomers are possible for :
find the value of X.
9. X = Number of chiral isomer of C5H12O. Find the value of X :
10. Number of allene possible of C3H2F2 (Including stereo)
O O
(A) (P) Four stereoisomers possible
CH3

(B) CH3 (Carbocation) (Q) C3-axis of symmetry
CH3
(C) CH 3–CH–CH–CH–CH 3 (R) One enantiomeric pair possible

Br Br Br
(D) CH4 (S) Plane of symmetry in atleast one of
the 3-Dimensional structure
(T) Two meso form
1. C 2. D 3. C 4. B 5. 32 6. 12
7. 7 8. 6 9. 8 10. 3
11. A-R ; B -Q,S; C -P,R,S,T ; D-Q,S
Solution
1. C
2. B
Cl Br Br
*
* * *
Cl
5. 32
TSI = 2n = 25 = 32
6. 12
CH3 H2C
OH
Sol. H2C OH H2C
• CH H3C OH
3 CH3
OH CH3
OH CH3
HO *
*
OH

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CONTENT

DPP-1 Optical Isomer, Chiral centre 04 – 10

DPP-3 Racemic Mixture 18 – 19

DPP-7 Plane of symmetry 39 – 44

DPP-8 Centre of symmetry 45 – 49

DPP-9 Axis of symmetry 50 – 55

DPP-11 Chiral, Achiral 57 – 65

DPP-13 Calculation of Optical 69 – 74

DPP-14 Calculation of stereoisomer, Part - 1 75 – 80

DPP-15 Calculation of stereoisomer, Part - 2 81 – 83

1. Which of the following have asymmetric carbon atom?

(A) (B) (C) (D)

CH3 CH3 CH3 CH3

(A) 8 (B) 9 (C) 10 (D) 11

(A) 7 (B) 8 (C) 9 (D) 10

(A) 5 (B) 6 (C) 7 (D) 8

(A) 4 (B) 2 (C) 3 ( D) 1

8. Choose the correct option for column-I and column-II.

(D) (S) It will not show geometrical isomerism

Integer Type Question

11. How many compounds have two chiral center ?

H3C O CH3 H3C O CH3

(V) (VI) (VII) (VIII)

Single Choice Question

One or more than one Type Question

Integer Type Question

10. 14 11. 3 12. 0 13. 3

CH3 CH3 CH3 CH3

1. Indicate the structure/s having R configuration.

3. Which of the following molecules is achiral ?

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

(A) I (B) II (C) III (D) IV

5. Which of the following represent (R)-2-butanol ?

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

7. Which structure represent (R)-1-chloro-1-fluoroethane ?

8. Which structure represents (S)-2-bromobutane ?

(A) I (B) II (C) III (D) None of the above

(A) (3R, 4S, 5R)-3,5-dichloro-4-methylhexane

(A) 2R, 4S (B) 2S, 4R (C) 2R, 4R (D) 2S, 4S

(A) I (B) II (C) III (D) IV

One or more than one Type Question

12. Indicate figure/s having S configuration.

(A) A-Q ; B-R ; C-P ; D - S

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

(5) (6) (7)

Single Choice Question

One or more than one Type Question

12. BCD 13. C

Integer Type Question

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

(A) –36º (B) 0º (C) +36º (D) unpredictable

4. The racemic mixture of Alanine can be resolved by using,

(1) (+)-2-Butanol (2) ()-2-Chlorobutanoic acid

5. The major product (ester) of the following reaction is

(A) A single stereoisomer (optically active)

(D) (+)-lactic acid and (–)-lactic acid

(C) CH3CH2CH2– (D) sec-Butylamine