BATCH XI, XII & DROPPER’S (Main & Advance)

TOPIC STEREOISOMERISM DPP 13

Marking Scheme : Single Correct (+3,-1) MM: 111 Time : 75 min

1. Optically active isomers but not mirror images are called

(a) Enantiomers (b) Mesomers (c) Tautomers (d) Diastereomers
2. Which will show geometrical isomerism ?
H Me Me Me
C C
(a) (b) (c) (d) HON NOH
NH NOH

3. The absolute configuration of the following compound is:

Me
H 2
Cl
Cl 3
H
Et

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

4. Geometrical isomerism is exhibited by
CH2 CH2 CHCl CHCl
(a) (b) (c) (d)

5. Which of the following compound is not chiral ?

(a) 1-Chloropentane (b) 3-Chloro-2-methyl pentane
(c) 1-Chloro-2-methyl pentane (d) 2-Chloropentane
6. Which of the following will have meso-isomer also ?
(a) 2-Chlorobutane (b) 2-Hydroxyopanoic acid (c) 2,3-Dichloropentane (d) 2-3-Dichlorobutane
7. Among the following which can have a meso form ?
(a) CH3CH(OH)CH(Cl)C2H5 (b) CH3CH(OH)CH(OH)CH3
(c) C2H5CH(OH)CH(OH)CH3 (d) HOCH2CH(Cl)CH3
8. Which of the molecules are expected to rotate the plane of a plane-polarized light ?
Ph
COOH CHO SH
H NH2
(a) H2N H (b) HO H (c) Et Et (d)
H NH2
H CH2OH H
Ph
9. Which one of the following conformations of cyclohexane is chiral?
(a) Boat (b) Twist Boat (c) Rigid (d) Chair
10. The number of stereoisomers obtained by bromination of trans-2-butene is
(a) 1 (b) 2 (c) 3 (d) 4

1
11. The number of structural isomers for C6H14 is
(a) 3 (b) 4 (c) 5 (d) 6
12. How many stereoisomers does the molecules have ? CH3CH==CHCH2CHBrCH3
(a) 2 (b) 4 (c) 6 (d) 8
13. The alkene that exhibit geometrical isomerism is
(a) Propene (b) 2-Methyl propene (c) 2-Butene (d) 2-Methyl-2-butene
14. A compound is formed by the substitution of two chlorine for two hydrogens in propane. The no. of
possible isomerie compounds is
(a) 4 (b) 3 (c) 5 (d) 2
15. The relationship between the following pair of compounds is
COOH H
H C Me HOOC C NH2
NH2 Me
(a) Homomers (b) Diastereomers (c) Enantiomers (d) Geometrical isomers
16. The two structures written below represent
CH 3 CH 2OH
HO H HO H
H OH H OH
CH 2OH CH 3
(a) Diastereomers (b) Enantiomers (c) Same molecule (d) Optically active
17. The most stable conformation of ethylene glycol is
(a) Anti (b) Gauche (c) Partially eclipsed (d) Fully eclipsed
18. In the Newman projection for 2,2-dimethylbutane, X and Y can respectively be
X
H3C CH3

H H
Y
(a) H and H (b) H and C2H5 (c) C2H5 and H (d) CH3 and CH3
19. For the compound X shown below, the number of asymmetrie centres, and optical property are
Br
X=
Br
(a) 2, optically active (b) 2,optically inactive (c) 3, optically activ (d) 3, optically inactive
20. Out of the following, the alkene that exhibits optical isomerism is
(a) 3-methyl-2-pentene (b) 4-methyl-1-pentene (c) 3-methyl-1-pentene (d) 2-methyl-2-pentene
21. Which of the following will show optical isomerism ?
H H Me Me
(a) HO C COOH (b) Me C COOH (c) Me C COOH (d) Me C COOH
H OH H Cl

2
22. Identify the compound that exhibits tautomerism:
(a) 2-Pentanone (b) Phenol (c) 2-Butene (d) Lactic acid
23. The most stable conformation of 1,2-dibromoethane
Br Br
Br Br H Br
H Br H H
(a) (b) (c) H (d) Br
H H H H H H H H
H Br H H

24. The following two compounds are

H

H
(a) Geometrical isomers (b) Functional isomers (c) Positional isomers (d) Optical isomers
25. The optically active compound is
COOMe COOMe COOMe COOH
HO H D OH H OH H OH
(a) (b) (c) (d)
HO H D OH H OH H OH
COOMe COOMe COOH COOH
26. The no. of optical isomers of the given compound CH3––CHBr––CHBr––COOH
(a) 0 (b) 1 (c) 3 (d) 4
27. (+) 2-chloro-2-phenylethane in toluene racemised slowly in the presence of small amount of SbCl5 due to
the formation of
(a) Carbanion (b) Carbene (c) Free-radical (d) Carbocation
28. Of the following, the oxime of which shows geometrical isomerism ?
(a) Acetone (b) Diethyl ketone (c) Formaldehyde (d) Benzaldehyde
29. The correct statement regarding the following compounds is
OH OH OH

(1) (2) (3)

OH OH OH
(a) all three compounds are chiral (b) only 1 and 2 are chiral
(c) 1 and 3 are diastereomers (d) only 1 and 3 are chiral.
30. Which of the molecules can exhibit optical activity ?
(a) 1-Bromopropane (b) 2-Bromobutane (c) 3-Bromopentane (d) Bromocyclohexane
31. The no. of isomers which are ethers and having the molecular formula C4H10O
(a) 2 (b) 3 (c) 4 (d) 5
32. The major product(s) obtained in the following reaction is/are
Me H Me Me Me Me
Br2 H Br H Br Br H Br H
(a) (b) (c) (d)
H Br Br H H Br Br H
H
Me Et Et Et Et
33. The total number of isomeric linear dipeptides which can be synthesized from racemic alanine is
(a) 1 (b) 2 (c) 3 (d) 4

3
34. The conformations of n-butane, commonly known as eclipsed, gauche and anti-conformations can be
interconverted by
(a) rotation around C––H bond of a methyl group (b) rotation of C––H bond of a CH2 grp
(c) rotation around C1––C2 linkage (d) rotation around C2––C3 linkage
35. With respect to the conformers of ethane, which of the following statements is true?
(a) Bond angle remains same but bond length changes
(b) Bond angle changes but bond length remains same
(c) Both bond angle and bond length change
(d) Both bond angles and bond length remains same
36. 3-Methylpent-2-ene on reaction with HBr in presence of peroxide forms an addition product. The number
of possible stereoisomers for the product is
(a) 6 (b) 0 (c) 2 (d) 4
37. Number of stereo centers present in linear and cyclic structures of glucose are respectively:
(a) 4, 5 (b) 5, 5 (c) 4, 4 (d) 5, 4

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

5
 DPP - 13 (STEREOISOMERISM)
01 (d) 02 (d) 03 (b) 04 (c) 05 (a) 06 (d) 07 (b) 08 (b)
09 (b) 10 (a) 11 (c) 12 (b) 13 (c) 14 (c) 15 (c) 16 (c)
17 (b) 18 (bd) 19 (a) 20 (c) 21 (b) 22 (a) 23 (b) 24 (c)
25 (c) 26 (d) 27 (d) 28 (d) 29 (d) 30 (b) 31 (b) 32 (ad)
33 (d) 34 (d) 35 (b) 36 (d) 37 (a)

6
 DPP - 13 (STEREOISOMERISM)
01

02

03

04

7
05

06

07

08

09

8
10

11

12

13

14

9
15

16

17

10
18

19

20

21

22

11
23

24

25

26

27

12
28

29

30

31

32

13
33

34

35

36

37

14
 BATCH XI, XII & DROPPER’S (Main & Advance)
TOPIC STEREOISOMERISM DPP SUPER SIXER 13A

Marking Scheme : Single Correct (+3,-1) M M: 81 Time : 1 hr

1. Among the following, the Newman projections of meso-2,3-butanediol are

Me Me Me Me
H OH H OH HO Me Me H
(i) (ii) (iii) (iv)
HO H H OH HO H H OH
Me Me H OH
(a) (i), (ii) (b) (i), (iii) (c) (iii), (iv) (d) (ii), (iv)
2. After the following interchange of groups in the Fischer projection of 2-bromobutane, the configuration
of X and Y will be
Br Me Me

H Me H Br H C Et
Et Et (X) Br (Y)
(a) X = R, Y = S (b) X = R, Y = R (c) X = S, Y = R (d) X = S, Y = S
3. Which one of the following compounds is optically active ?

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

4. The stable form of trans-1,4-dimethylcyclohexane is represented as

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

Me Me
5. Among the following, the most stable conformations of meso-2,3-dibromobutane is
Br Br Br Br
Br Me H Me H Me Me Br
(a) (b) (c) (d)
H Me Me H H Me H Me
H Br Br H
6. The following compounds are CHO CH2OH
(a) ldentical (b) Diastereomeric H OH H OH
(c) Enantiomeric H Cl H Cl
(d) Constitutionally isomeric CH2OH CHO
7. Which of the following is a chiral ?
(a) Alanine (b) Glycine (c) Proline (d) Phenylalanine

1
8. The maximum no. of stereoisomers possible for 4-Phenylbut-3-en-2-ol is
(a) 1 (b) 2 (c) 3 (d) 4
9. Among the following compounds, the pair of enantiomers is
COOH CH2OH CH 2OH NH2
H Br H Br H2N H H CH2OH
(i) (ii) (iii) (iv)
H2N H H NH2 H Br H COOH
CH 2OH COOH COOH Br
(a) (i) and (iv) (b) (i) and (iii) (c) (ii) and (iii) (d) (iii) and (iv)
10. In the compound given below, the relation between H , H ; and between Br1, Br2 is
A B

HA HB

Me Me

Br Br
1 2

(a) HA, HB are enantiotopic; Br1, Br2 are diastereotopic

(b) HA, HB are diastereotopic; Br1, Br2 are enantiotopic
(c) HA, HB are diastereotopic; Br1, Br2 are homotopie
(d) HA, HB are enantiotopic; Br1, Br2 are homotopie
11. The no. of all possible isomers for molecular formula C6H14 is
(a) 5 (b) 6 (c) 7 (d) 8
12. Among the following, the most stable isomer for 3-methoxycyclohexanol is
OMe
OH OMe OH
(a) (b) (c) (d)
OMe OMe OH
HO
13. Among the following, the correct statement concerning the optical activity is
(a) A molecule containing two or more ehiral centres is always optically active
(b) A molecule containing just one chiral centre is always optically active
(c) A molecule possessing alternating axis of symmetry is optically active
(d) An optically active molecule should have at least one chiral centre
14. Among the following, the no. of molecules that possess C2 axis of symmetry is
Me Me
Cl Cl Cl Cl
BF3 CHCl3 C
S
H H H H
Me Me
(a) 5 (b) 6 (c) 7 (d) 8
15. The pair of conformation that has maximum energy difference is

(a) and (b) and

(c) and (d) and

2
16. The absolute configurations at the two chiral centres in D-Ribose are
CH2OH
C O
H C OH
H C OH
D-Ribulose
CH2OH
(a) 3R, 4R (b) 3R, 4S (c) 3S, 4R (d) 3S, 4S
17. The species/compounds that are aromatic among the following are

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

(a) (iii) and (iv) (b) (i) and (ii) (c) (ii) and (iv) (d) (i) and (iv)
18. Specific rotation of the (R)-enantiomer of a chiral compound is 48. The specific rotation of a sample of
this compound which contains 25% of (S)-enantiomer is
(a) 24 (b) 36 (c) 48 (d) 96
19. The structure of (2S,3R)-2-amino-3-hydroxy butanoic acid is
COOH COOH COOH COOH
H NH2 H2N H H2N H H NH2
(a) (b) (c) (d)
HO H HO H H OH H OH
Me Me Me Me
20. Optically active 2-octanol rapidly loses its optical activity when exposed to
(a) dilute acid (b) base (c) light (d) humidity
21. The absolute configuration of the two stereogenic (chiral) centres in the following molecule is
(a) 5R,6R
O
(b) 5R,6S
(c) 5S,6R
(d) 5S,6S

22. The compounds having C2-axis of symmetry are

Me Me Br Me

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

Me Me Me Me Br Br Me Me
(a) (i), (iii) and (iv) (b) (i), (ii) and (iii) (c) (i) and (iii) (d) (iii) and (iv)
23. Consider the following statements about cis- and trans- decalins
(i) cis- isomer is more stable than trans- isomer (ii) trans- isomer is more stable than cis- isomer
(iii) trans- isomer undergoes ring-flip (iv) cis- isomer undergoes ring-flip
(a) (ii) and (iv) (b) (i) and (iii) (c) (i) and (iv) (d) (ii) and (iii)

3
24. The correct statement about the following molecule is

Br
(a) Molecule is chiral and possess a chiral plane
(b) Molecule is chiral and possess a chiral axis
(c) Molecule is achiral as it possesses a plane of symmetry
(d) Molecule is achiral as it possesses a centre of symmetry
Br
25. The absolute configurations of the two chiral centres in the following molecule
(a) 2R,3S (b) 2R,3R (c) 2S,3S (d) 2S,3R
26. The absolute configuration for compounds X and Y respectively are
OH
Et Me Br
(X) (Y) C

Me H H
H
(a) R, S (b) S, R (c) R, R (d) S, S
27. the stereochemical notations For the compound are
OH
OH

O
(a) 2Z, 4R (b) 2Z, 4S (c) 2E, 4R (d) 2E, 4S

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

5
 BATCH XI, XII & DROPPER’S (Main & Advance)
TOPIC STEREOISOMERISM DPP SUPER SIXER 13B

Marking Scheme : Single Correct (+3,-1) M M: 81 Time : 1 hr

1. Among the following carboxylic acids shown below, the ones that exhibit stereoisomerism and also form,
cyclic anhydrides on heating are
(i) HOOCCH(Me)CH2CH2COOH (ii) HOOCCH(C3H7)COOH
(iii) HOOCCH(Et)CH2COOH (iv) HOOCC(Me)(Et)COOH
(a) (i), (ii) (b) (i), (iii) (c) (ii), (iii) (d) (ii), (iv)
2. Consider the following reaction, the absolute configurations of the chiral centres in X and Y are
CHO
H OH
HCN
X + Y
CH2OH
(D-glyceraldehyde) (2 diastereomers)
(a) (2S,3R) and (2R,3R) (b) (2R,3R) and (2R,3S) (c) (2S,3S) and (2R,3R) (d) (2S,3R) and (2S,3R)
3. The most stable conformation of the following compound is
Me
Me

t
Bu
4. Among the following, the optically inactive compound is

Et N Me P Me
(a) Me (b) (c) C (d)
Me
H COOH
OH
5. The total no. of pair of enantiomers possible with molecular formula C5H12O is....
6. For the aldotetroses I-IV, the combination of the true statements, among P-T, is
CHO CHO CHO CHO
H OH H OH HO H HO H
(i) (ii) (iii) (iv)
H OH HO H H OH HO H
CH2OH CH 2OH CH 2OH CH 2OH
P = (i) and (iii) are diastereomers and (ii) and (iii) are enantiomers;
Q = (i) and (iv) are mesomers and are optically inactive;
R = (i) and (iii) can be inter-converted by a base catalysed isomerization;
S = only (i) and (iv) are HIO4 cleavable;
T = (i) and (iii) are D-sugars and (ii) and (iv) are L-sugars
(a) Q,R,T (b) P,R,T (c) Q,R,S,T (d) P,Q,S

6
7. The correct sequence of relationship between the compounds of the following pairs 1-4 is
Et Me Ph Me Et Me
COOH Me
H Br H Br HO H H NH2 H Cl Cl H
(i) H NH2 H NH2 (ii) Br H Br H
(iii) H N H HO H
(iv) H Br Br H
Me COOH
2

Me Et Me Ph Me Et

(a) identical, enantiomers, diastereomers and structural isomers

(b) enantiomers, identical, structural isomers and diastereomers
(c) enantiomers, identical, diastereomers and structural isomers
(d) identical, identical, diastereomers and structural isomers
8. The Cahn-Ingold-Prelog (CIP) priorities of the groups and the absolute configuration (R/S) of the following
compound are OH

C
(Me)2HC Me
(a) ––CH2OH > ––CH(Me)2 > ––CH==CH2 > ––CH3 and S
(b) ––CH2OH > ––CH==CH2 > ––CH(Me)2 > ––CH3 and S
(c) ––CH2OH > ––CH==CH2 > ––CH(Me)2 > ––CH3 and R
(d) ––CH2OH > ––CH(Me)2 > ––CH==CH2 > ––CH3 and R
9. The configurations of the reactant and the product in the following reaction, are
CO2CH3 CO2CH3
KCN / EtOH
D Br CDCN
H H
(a) R,R (b) R,S (c) S,R (d) S,S
10. The molecules(s) that exist as meso structure(s) is/are

(K) (L) (M)

(a) only M (b) both K and L (c) only L (d) only K

11. Among the following amino acids, the (R)-enantiomer is represented by
CH3 COOH NH 2 COOH
(a) H2N COOH (b) H NH2 (c) H3C H (d) H3C NH2
H CH3 COOH H
12. The number of enantiomers of camphor is

O
(a) 4 (b) 3 (c) 2 (d) 1
13. In the most stable conformation of trans-1-t-butyl-3-methylcyclohexane, the substituents at C-1 and C-3
respectively, are
(a) axial and equatorial (b) equatorial and equatorial (c) equatorial and axial (d) axial and axial

7
14. The gauche interaction values for Me/Me, Me/Br and Br/Br are 3.3, 0.8 and 3.0 kJ/mol, respectively.
Among the following the most stable conformation of 2,3-dibromobutane is
Br Br Br Br
Me Br H Me H Br Br Me
(a) (b) (c) (d)
Me H Me H Me H Me H
H Br Me H
15. Ring flipping of the compound in the following conformation leads to

Br CH3
HO

OH OH
Me Me Me
(a) (b) Br (c) (d) Br
Me
Br Br
HO OH
16. The absolute configuration of C-2 and C-3 in the following compound is
O
OH H

H3C OH
Br H
(a) 2R,3S (b) 2S,3R (c) 2S,3S (d) 2R,3R
17. In the following Markownikoff's addition reaction, the products A and B are
HBr
A + B
Br
(a) Homomers (b) Enantiomers (c) Diastereomers (d) Regioisomers
18. The no. of possible stereoisomers obtained in the following reaction is:
Me

(1) O3 / Zn
(2) excess PhMgBr
H3O


19. An optically active eompound enriched with R-enantiomer (60% ee) exhibited [  ]D = +90°. If the [  ]D
value of the sample is –135°, the ratio of R and S enantiomers would be
(a) R : S = 1 : 19 (b) R : S = 19 : 1 (c) R : S = 1 : 9 (d) R : S = 9 : 1
20. The no. of possible stereoisomers for cyclononene is:
21. Identify two enantiomers among the following compounds.
Br H Br CH3 Br H Br CH3
H3C H3C H3C H3C
(i) (ii) (iii) (iv)
CH3 H CH3 H
H Br Br H Br H H Br
(a) (i) and (ii) (b) (i) and (iii) (c) (ii) and (iv) (d) (iii) and (iv)

8
22. The most stable conformations of 1,2-difluoroethane and dl-2,3-butanediol are
F OH F OH
H F Me H H H Me OH
(a) (b)
H H Me H H H H Me
H OH F H
F OH F Me
H H H OH H F H OH
(c) (d)
H H Me H H H H OH
F Me H Me
23. Given the energy of each gauche butane interaction is 0.9 kcal/mol, DG value (in kcal/mole) of the
following reaction is

H 2, Pd, 250°C

(a) 0.9 (b) 1.8 (c) 2.7 (d) 3.6

24. Catalytic hydrogenation of the following compound produces saturated hydrocarbon(s). The no. of
stereoisomer(s) formed is
Me Me
Me

Me
(a) 1 (b) 2 (c) 3 (d) 4
25. The [  ]D of a 90% optically pure 2-arylpropanoic acid is +135°. On treatment with a base at RT for one
hour, [  ]D changed to +120°. The optical purity is reduced to 40% after 3 hours. If so, the optical purity
of the solution after 1 hour, and its [  ]D after 3 hours, respectively, would be
(a) 80% and 60° (b) 70% and 40° (c) 80% and 90° (d) 70% and 60°
26. Among the structures given below, the most stable conformation for the following compound is

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

9
27. Match the Columns
Column I Column II
NO2
NO2

(p) (i) Chiral centre

Me
Me

(q) (ii) Chiral axis

(r) (iii) Chiral plane

(iv) Helical chirality

Me Me

(a) (p)-(iii), (q)-(ii), (r)-(iv) (b) (p)-(iv), (q)-(iii), (r)-(ii) (c) (p)-(ii), (q)-(iv), (r)-(iii) (d) (p)-(ii), (q)-(iii), (r)-(iv)

10
All students are advised to solve DPPs within allowed time only.
All discussions are scheduled in every 4th doubt discussion class
–MKA Sir (Guruji)

11
 DPP - SUPER SIXER 13A (STEREOISOMERISM)
01 (c) 02 (c) 03 (d) 04 (c) 05 (b) 06 (b) 07 (b) 08 (d)
09 (b) 10 (b) 11 (a) 12 (a) 13 (d) 14 (c) 15 (a) 16 (a)
17 (d) 18 (a) 19 (c) 20 (a) 21 (c) 22 (c) 23 (a) 24 (a)
25 (d) 26 (c) 27 (d)

DPP - SUPER SIXER 13B (STEREOISOMERISM)

01 (b) 02 (a) 03 (c) 04 (a) 05 (d) 06 (d) 07 (c) 08 (b)
09 (d) 10 (b) 11 (b) 12 (c) 13 (c) 14 (b) 15 (b) 16 (d)
17 (c) 18 ( 8 ) 19 (a) 20 (d) 21 (d) 22 (d) 23 (b) 24 (c)
25 (a) 26 (c) 27 (d)

12
 DPP - SUPER SIXER 13A (STEREOISOMERISM)
01

02

03

13
04

05

06

07

14
08

09

10

11

15
12

13

14

15

16
16

17

18

19

17
20

21

22

23

18
24

25

26

27

19
 DPP - SUPER SIXER 13B (STEREOISOMERISM)
01

02

CN CN
CHO
HCN H OH HO H
H OH +
H OH H OH
CH 2OH
(D-glyceraldehyde) CH2OH CH 2OH

20
03

04

05

06

07

21
08

09

22
10

11

12

13

23
14

15

16

17

24
18

19

20

21

25
22

23

24

26
25

26

27

27