Optical Isomerism Part-01

Optical Isomerism DPP-01

1. How many chiral carbon atoms are present in following molecule ?

C2H5
|
CH3 — CH — CH — CH — CH3
| |
Cl CH3
(1) 1
(2) 2
(3) 3
(4) 4

2. Which of the following molecule has chiral carbon ?

Me

(1) Cl CH 3

(2)

Et

(3) H Me

(4)

3. Which one of the following contains asymmetric carbon atom?

Cl Br
(1) H—C—C—H
H H
H Cl
(2) H—C—C—Cl
H H
H H
(3) H—C—C—H
H H
H H
(4) H—C—C—CH3
Br OH

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Optical Isomerism Part-01

4. An organic compound exhibits optical isomerism when

(1) Four groups linked to carbon atom are different
(2) Three groups linked to carbon atom are different
(3) Two groups linked to carbon atom are different
(4) All the groups linked to carbon atom are same

5. Rotation of plane polarised light is measured by

(1) Manometer
(2) Polarimeter
(3) Viscometer
(4) Refractometer

6. Which of the following contains asymmetric centre

(1) 2-Butene
(2) 2,2-Dimethylpropane
(3) 2-Hexyne
(4) Lactic acid

7. Which of the following has chiral carbon

(1)
(2) CH3—CH=CH—CH3

(3)
(4) CH3—CHOH—CH2CH3

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Optical Isomerism Part-01

Answer Key
Question 1 2 3 4 5 6 7
Answer 2 4 4 1 2 4 4

SOLUTIONS DPP-01
C2H5
1. * – CH – CH – CH
CH3 – CH 3
*
Cl CH3
Cl
2. I * Br All four valencies
are different
F

H H
3. H C C * CH3
Br OH

4. An organic compound exhibits optical isomerism when four groups linked to carbon atom are different.

5. Polarimeter

COOH
6. *
H OH Lactic acid

CH3

H H
7. CH3 *C C CH3
OH H

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Optical Isomerism Part-04

Optical Isomerism DPP-02

1. Which of the following molecule is chiral:-

(1) Isobutane
(2) Neopentane
(3) Sec-butylchloride
(4) All

2. Which one of the following shows optical activity?

(1)

(2)

(3)

(4)

3. Which of the following compounds is not chiral?

(1) DCH2CH2CH2Cl

(2) CH3CH2CHDCl

(3) CH3CHDCH2CH2Cl

(4) CH3CHClCH2D

4. Which of these molecule is optically active?

(1) I
(2) II
(3) II
(4) All of these

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Optical Isomerism Part-04

5. Which is optically active?

(1) H3C CH3
Cl

(2) HO CH3

COOH
H OH
(3) H OH
COOH

(4)

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Optical Isomerism Part-04

Answer Key
Question 1 2 3 4 5
Answer 3 2 1 4 4

SOLUTIONS DPP-02

1. Sec-butylchloride
* – CH – CH
CH3 – CH 2 3

Cl
H

2. CH3 *
– C – COOH

Cl

3. CH2 – CH2 – CH2 – Cl

No chiral center

CH3 C2H5 CH3

H * Br
H * Br H * Br
4. H * Br
C2H5 CH3 C2H5

No POS/COS

*
*
5.
*

No POS/COS

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Optical Isomerism Part-06

Optical Isomerism DPP-03

1. Which of the following has 'S' configuration:-

(1)

F
(2) C—H
H 3C
CH 2 CH 3

H
(3) C—F
H 3C
CH 2 CH 3

CH 3

(4) F H

CH 2 CH 3

2. The configuration of the compound

(1) R
(2) S
(3) Z
(4) E

3. (2R,3R)-2,3-Butanediol is:-
CH 3
(1) HO H
H OH
CH 3
CH 3
(2) H OH
HO H
CH 3

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Optical Isomerism Part-06

(3)

CH 3
H
(4) HO
HO H
CH 3

4. Among the following L-serine is

(1)

(2)

(3)

(4)

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Optical Isomerism Part-06

Answer Key
Question 1 2 3 4
Answer 3 1 1 3

SOLUTIONS DPP-03
4 CH3 1
H F
1 1st 2nd 3
1. C F C F C CH3
3
CH3 2 H 4H
CH2 – CH3 CH2 – CH3 2CH – CH
2 3

S
4th priority should be on dash

2.

3
CH3
1 4
HO H R
2 2
1
3. H OH R
4 H
3 CH3

2R,3R

NH2 COOH

4. H COOH H2N H

CH2OH CH2OH
(L-serine)

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Optical Isomerism Part-07

Optical Isomerism DPP-04

1. Which of the following compounds is Erythro?

CHO
H ` OH
(1) HO H
CH2OH
CHO
H ` OH
(2) H OH
CH2OH
CHO
H ` Cl
(3) H Cl
CH2OH
(4) Both 2 & 3

2. D & L Configuration is applied for :-

(1) Amino acids
(2) Carbohydrates
(3) Both 1 & 2
(4) None of these

3. Erythro & Threo are the pair of :-

(1) Enantiomers
(2) Diastereomers
(3) Identical
(4) Meso compounds

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Optical Isomerism Part-07

Answer Key
Question 1 2 3
Answer 4 3 2

SOLUTIONS DPP-04

1. Erythro  same groups same side

CHO CHO

H ` OH H ` Cl
H OH and H Cl are Erythro

CH2OH CH2OH

2. D & L Configuration is applied for amino acids and carbohydrates.

3. Erythro & Threo are the pair of diastereomers because they are not mirror images of each other.

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Optical Isomerism Part-10

Optical Isomerism DPP-05

1. The following two compounds are

Cl Br
H F and F Cl
Br H
(1) Enantiomers
(2) Diastereomers
(3) Identical
(4) Epimer

2. Which of the following can show enantiomerism?

CH3
|
(1) CH3 − CH − COOH
(2) CH2 = CHCH2CH2CH3
NH2
|
(3) CH3 − CH − CH3
NH2
|
(4) CH3 − CH2 − CH − CH3

3. Meso-tartaric acid is optically inactive due to the presence of

(1) Molecular symmetry
(2) Molecular asymmetry
(3) External compensation
(4) Two asymmetric C-atom

4. Which of the following can be a meso compound?

(1)

(2)

(3)
Br
(4) All of these

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Optical Isomerism Part-10

5. Which of the following compound will not show optical isomerism

CH3
(1)
CH3
CH3

(2)

CH3
CH3

(3)

CH3

(4) All of these

6. Among the following aldose which is D-threose

(1)

(2)

(3)

(4)

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Optical Isomerism Part-10

Answer Key
Question 1 2 3 4 5 6
Answer 1 4 1 2 2 4

SOLUTIONS DPP-05

2 Cl 1 Br
4 3 3 2

1.
H F F Cl

1 Br 4 H
S R

Enantiomers
*
2. CH3 – CH2 – CH – CH3

NH2

COOH
H OH POS
3. H OH

COOH

POS

4. *
*

Meso compound

CH3

5.

CH3
Does not show optical isomerism

6.

D-threose

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Optical Isomerism Part-11

Optical Isomerism DPP-06

1. Which of the following is not optically active –

(1) CH3 —CH = C = CH —CH3
(2) CH2 = C = CH2

(3)

(4)

2. Which of the following biphenyl is optical active:

(1)

(2)

(3)

(4) None

3. Which of the following will not be able to show optical isomerism?

(1) 1,2-Propadiene
(2) 2,3-Pentadiene
(3) sec-Butyl alcohol
(4) 2, 3-Butanediol

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Optical Isomerism Part-11

Answer Key
Question 1 2 3
Answer 2 2 1

SOLUTIONS DPP-06

1. Cumulene containing even number of  bonds with different groups on each sp2 carbon are optically active.

Same H H Same
Groups C=C=C Groups
H H

Optically inactive.

2. Biphenyl having different bulky groups at ortho positions become perpendicular with respect to each other,
hence do not contain any element of symmetry.
I I

O O

Br Br

H H
3. C=C=C Same groups
H H
(Propadiene)
CH3 CH3
C=C=C Different groups
H H
on each sp2 carbon
(Penta-2,3-diene)

It shows optical activity

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Optical Isomerism Part-12

Optical Isomerism DPP-07

1. Calculate total number of optical isomers in following compound:-

CH3 — CH — CH— CH3
| |
OH OH
(1) 4
(2) 3
(3) 2
(4) 1

2. Number of optical isomers of lactic acid are

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

3. The maximum number of stereoisomers possible for 2-hydroxy-2-methyl butanoic acid is

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

4. The number of enantiomeric pairs of the compound CH3CHBrCHBrCOOH is

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

5. How many stereoisomers are possible for following compound?

(1) 2
(2) 3
(3) 4
(4) 5

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Optical Isomerism Part-12

6. Total number of stereoisomers for

CH3 — CH = CH — CH — CH = CH — C2H5
|
CH3
(1) 2
(2) 4
(3) 6
(4) 8

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Optical Isomerism Part-12

Answer Key
Question 1 2 3 4 5 6
Answer 2 2 2 1 2 4

SOLUTIONS DPP-07
* *
1. CH3–CH–CH–CH3 (symmetrical)
OH OH
n=2
n
−1
Total no. of stereoisomers = 2 n −1 + 2 2
2
−1
= 2 2 −1 + 2 2
= 21 + 20
=2+1
=3

H
*
2. CH3–C–COOH
(unsymmetrical)
OH
n=1
no. of optical isomers = 2n
=2

CH3
*
3. CH3–CH2–C–COOH
(unsymmetrical)
OH
n=1
total no. of stereoisomer = 2n = 2

H H
*
4. CH3*–C–C–COOH
(unsymmetrical)
Br Br
n=2
Total no. of enantiomers = 2n = 22 = 4

* Br
5. *
Br
cis trans

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Optical Isomerism Part-12

*
CH3– CH=CH–CH –CH=CH– C2H5
6.
CH3
(unsymmetrical)
n = no. of chiral center + no. of double bond
Total no. of stereoisomers = 2n = 23 = 8

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