organic chemistry

DPP-10 Time: 20 Minutes

Q.1 Compound P.O.S. C.O.S. Optically active

1.
CH3 CH3

H H

2.
H CH3

CH3 H

3. H
H
CH3
CH3

H H
4.

CH3 CH3

5. H H

Cl Cl

6. Cl H

H Cl

7. Br
Cl H
Cl
H Cl
H
8. H
Cl
H
Cl
Cl
9. H H
C=C=C
Cl Cl

10. H Cl
C=C=C
Cl Br

11. H H
C=C=C=C
Cl Cl

12. H H
C C
Cl Cl

13. Cl H
C C
H Cl

14. H H
Cl Cl

15. H
CH 3
CH3

16. Cl H
H Cl

17.

C
H Cl
CH3 CH3
18.

C
H H
 CH3 CH3
19.

C
H Cl

20.

21.

22. Cl I

I Cl

23.

24. O = C = O

25. H
O=C=O

H H
26. O=C=O

27.
N=N=N
H H
H
28. C No. of POS _ _ _ _ _ _ _ _
H H
H
H
29. C No. of POS _ _ _ _ _ _ _ _
Cl H
H
 H H
C=C
30. No. of POS _ _ _ _ _
CH 3 CH 3

CH 3
H
C=C
31. No. of POS _ _ _ _
H CH 3

Q.2 Match the following structural formulae with their possible geometrical isomers?
Column-I Column-II
(Structural formula (Total geometrical isomers excluding
mirror image)

(A) CH3 – CH = CH CH2 – CH3 (P) 8

CH=CH–CH 3
(B) CH3 – CH = C (Q) 6
CH=CH–CH 3

(C) CH3 – CH = CH CH = CH – CH3 (R) 4

(D) Cl – CH = CH – CH = CH – CH = CH – CH3 (S) 2

H5 C2 C l H C
5 2
Cl
Q.3 Statement 1: C=C and C=C are structural
CH3 Br Br CH3
Statement 2: The above mentioned compounds can show geometrical isomerism.
(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for statement-1.
(B Statement-1 is true, statement-2 is true and statement-2 is NOT correct explanation for
statement-1.
(C) Statement-1 is false, statement-2 is true.
(D) Statement-1 is true, statement-2 is false.

Q.4 Which compound(s) will show Geometrical isomerism? H

CH3 Cl Cl
N O
N–H CH3
(A) (B) C=C=C (C) (D)
H3 C
O N
H H
H

Q.5 Find out the correct option(s) ?

NH
CH3 CH3 CH3
(A) C=C Orientation is E (B) Orientation is Z
NH H H
H
 D
C=C
CH3
(C) H Orientation is Z (D) geometrical isomers are not possible
CH3

Q.6 Calculate total number of geometrical isomers in following compounds. (Excluding mirror image)
(i) CH3 – CH = CH – CH = CH – CH = CH – CH3

(ii) CH2 = HC CH = CH – Me
(iii) Me – CH = C = CH – CH2 – CH = C = C = CH – Me

Me
(iv) (v)
D
(vi) Br – CH = C = C = CH – CH = CH – Br
 organic chemistry
Date: DPP- 11 Time: 15
minutes
Q.1 How many chiral carbon atoms are present in the following compounds?

H O H O
N PhOCH2 – C – NH S
(i) (ii)
CH3 N
H O COOH
Coccinellin Penicillin V

COOH
(iii) (iv)

HO
Estrone Betulinic acid

Q.2 Assign priority number to the following groups as per Cahn, Ingold, Prelog sequence rule
(a) – CH2OH, –CH3, –CH2CH2OH, –H
(b) – Cl, –Br, –CH = CH2, –CH3
O
(c) – C – H , –OH, – CH3, – CH2OH

(d) – CH(CH3)2, –CH2CH2Br, –Cl, –CH2CH2CH2Br

(e) – CH = CH2, – CH2CH3, , – CH3

CH3 CH3
(f) – CH = CH2, –C CH, – CH – CH2 – C – CH
CH3 CH3 CH3 CH3
(g) – CH2CH2CH2I – CH – CH – CH3 – CH – CH2CH3 –F
Br Cl

Q.3 Indicate whether each of the following structure has the R configuration or the S-configuration.

CH(CH3)2 CH2 – Br Br CH2 – Br D

(a) C CH2CH3 (b) C (c) C (d) C (e) C
CH2CH2Cl H OH CH3
CH3 CH2 – Br CH3CH2 Cl H CH3CH2 H
OH F CH3

Br Cl H CH =CH2 SH
(f) C (g) CH3 CH2CH3 (h) CH3CH2 F (i) F OH (j) H NH2
H
CH3CH2 CH3 Me
H Cl CH3
 CH2 – Br
H NH2
CH3 CH2CH3 CHO CH3
CH2
(k) H Cl (l) (m) CH3 CH2I (n) H OH (o) H COOH

CH2 – CH3 H CH2 – OH CH2 – CH3

CH3 CH3 CH3 CH2CH3

CH2 – OH
HO H Br H H Br CH3 H
(p) HO CH3 (q) H Cl (r) H Br (s) H Br (t) Br CH3
CH2CH3 CH2CH3 CH2CH3 CH2CH3
CH2CH2CH2OH

COOH
H OH
(u) H OH
COOH

Q.4 Indicate whether each of the following structure has the R configuration or the S-configuration.

CH = CH2 CH2 – Cl F CH2 – OH

(a) C CH3 (b) C CH2CH2Cl (c) C CH3 (d) C OCH3 (e)
H CH3 OH D
COOH SH NH2 T
CH3
C OCH3
CH3O 18
H
I SO3H NH2 CH3 CH2CH3 SR
(f) C D (g) DCH2 SCH3 (h) CH2 CH2OH (i) (j) H NR2 (k)
HS
NH2 CH3
CH3 CH2F Et
CH2OH
CH2CH3 CH3 OPh CH3 COOH Me

CH3 I (l) (m) D CH2Cl (n) H OH (o) D CHO

CH2CH2CH3 H CH3 Et

CH2NH2 Me CH3 CH2Cl CH2CH3

(p) H2N CH2CH3 (q) H2N D (r) I Et (s) H OMe (t) CH3 H
D Br CH3 I H Br I H
CH2CH2CH2NH2 CH2CH2CH3 CH2CH2CH3 CH2CH3 CH2CH3
2 2 2 2

SO3H CH2CH2CH2COOH Et CH2CH2CH3

H Cl CH3 H Me D Cl H
(u) H (v) H (w) HO D (x) Br H
Cl CH3
SO3H CH2CH3 CH2CH2CH3
COOH
H OH
H OH H
(y) (z) CH3
H OH
CH2OH
 organic chemistry
DPP NO- 12 Time: 15 minutes
Q.1 Column-I Column-II
Cl O

(A) Me (P) Total number of stereo isomers are odd.

Me Cl
Br
(B) (Q) Total number of stereocenter are even or have

Br
centre
H Cl
C
(C) (R) Compounds having plane of symmetry or axis of
C
Cl H
symmetry
COOH
H OH
(D) (S) Compounds have zero dipole in given form.
HO H
COOH

Q.2 Column-I Column-II

H Me
(A) Plane of symmetry (P) C C
Me H
Me Me

(B) Centre of symmetry (Q)

Me
H
(C) Meso Compound (R) C
Me

Ph COOH

OOH
(D) Chiral atom is / are present (S) C H Ph H

H H
Cl H
(T) C=C=C=C
H Cl
Comprehension (Q.3 to Q.5)
 On the basis of the following set of compounds, answer the following questions.
CHO H CH2 OH CHO CHO
HO H HOH 2C OH H OH H OH HO H
H OH HO H (III) HO H HO H HO H
(I) H OH (II) HO H H OH (IV) HO H (V) HO H
HO H HO H H OH H CH2 OH HO H
CH2OH CHO CHO OH CH2 OH

Q.3 Which of the following represent enantiomeric pair?

(A) I & II (B) II & V (C) I & V (D) II & IV
(E) III & V

Q.4 Which of the following does not represent active diastereomeric pair?
(A) III & IV (B) I & II (C) I & III (D) I & IV
(E) None of these

Q.5 Which of the following represent ‗D‘ sugar.

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

Q.6 Select the pair of enantiomer and diastereomers out of the following:
CH3 CH3 CH3 CH3 H CH3 CH3 H

H H H H CH3 H H H3 C

H CH3 H3 C H H CH3 H3 C H
A B C D s

Q.7 Which of the following compounds should have the larger energy barrier to rotation about the
indicated bond ?
(a) Me3C CMe (b) Me3Si SiMe3

Q.8 How many compounds are theoretically possible for formula C3H6O (excluding stereoisomers)?

Q.9 How many acyclic isomers of C5H10 are possible which are incapable of showing Optical
Isomerism?

Q.10 How many stereoisomers are possible for the following?

Me CH=CH–CH=CH 2

Me CH=C=C=CH–Me
(A) 16 (B) 4 (C) 6 (D) 8

Paragraph for question nos. 11 to 13

Answer the following questions based on given reaction

Cl2
hv
Products.
(monochlorination)

Q.11 The number of theoretically possible products (including stereo) are

(A) 6 (B) 8 (C) 10 (D) 12

Q.12 How many products are resolvable.

(A) 4 (B) 6 (C) 8 (D) 10
36
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Q.13 How many factions are present on fractional distillation?
(A) 4 (B) 5 (C) 6 (D) 8

Q.14
(a) How many plane of symmetry are present in prismane (C6H6)?

(b) How many chiral centres are present in the following compound?
O
Ph
S
O
Br
(c) Minimum carbon atoms required for an alkane to show optical isomerism.

37
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 organic chemistry
Date: DPP NO- 13 Time: 15
minutes
Q.1 Column-I Column-II
H CO2 H
OH
(A) (P) chiral
OH
CO2 H H
CO2 H H
OH
(B) (Q) achiral
OH
OH CO2 H
H
CO2 CH2 CH2 OH
(C) (R) meso
CO2 H
H
H H
CO2 CH2 CH2 O2 C
(D) (S) compounds containing even number of chiral
CO2 CH2 CH2 O2 C
H H
center

Q.2 Column-I Column-II

Cl Cl Cl Cl

(A) and are (P) Structural isomers

H Me Me H
CH3 CH3 CH3 H

(B) and are (Q) Compounds are optical

H H H CH3
isomers and enantiomers
Me H
Me H C
C C
(C) and Et are (R) Compounds which are
C O CH3 geometrical isomer and
C
H CH2–CH2–COOH diastereo isomers
O
COOH COOH
(D) H OH and HO H are (S) Compounds are
H OH HO H
COOEt COOEt
geometrical
isomers and enantiomers
(T) Not isomers

38
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 F F

Q.3 Statement 1:

F F
(I) (II)
(I) and (II) are optically inactive molecules.
Statement 2: Molecules containing plane of symmetry or centre of symmetry are optically inactive.
(A) Statement-1 is true, statement-2 is true and statement-2 is correct explanation for statement-1.
(B Statement-1 is true, statement-2 is true and statement-2 is NOT correct explanation for
statement-1.
(C) Statement-1 is false, statement-2 is true.
(D) Statement-1 is true, statement-2 is false.

Q.4 Minimum C atoms required for a compound to show geometrical isomerism:

(A) 2 (B) 3 (C) 4 (D) None of these

Q.5 The correct stability order of the following species is

H H Me
Me H Me

Me
H Me
H H Me
(a) (b) (c)
(A) c < a < b (B) c = b < a (C) c < a = b (D) a = b = c

Me
Q.6 This compound shows:
Et
(A) geometrical isomerism (B) optical isomerism
(C) both (D) none

Q.7 (+)-Tartaric acid has a specific rotation of +12.0°. Calculate the specific rotation of a mixture of 68%
(+)-trataric acid and 32% (–)- tartaric acid.
(A) 4.32° (B) – 4.32° (C) – 12° (D) 12°

Paragraph for question nos. 8 to 10

24 gm of optically pure tartaric acid is dissolved in water to make 240 ml solution. It is kept in 20 cm
polarimeter tube & plane polarized light is passed through it to product rotation of –2.4°.
Q.8 If mixture of d and l tartaric acid has the specific rotation – 4.0°, calculate the % of optical purity of
this mixture?
(A) 50% (B) 66.67% (C) 33.33% (D) None

Q.9 Calculate the % of d tartaric acid in a mixture of d and l tartaric acid which has the observed specific
rotation + 6.0°.
(A) 25% (B)75% (C) 50% (D) 66.67%

Q.10 If original solution is diluted by 2 times and length of polarimeter is increased four times of previous
length. What will be the specific rotation.
(A) – 4.8 (B) + 4.8 (C) – 6 (D) – 12
39
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Q.11 Select resolvable compounds.
HO

(A) (B) Cl
O
N
OH
CH3 O
H

H
H Me O

(C) (D) O N–H

CH3 O
H

Q.12 Calculate total number of stereocentre, prochiral carbon and theoretical stereoisomer in the
following compound.

N
S
O

Number of stereocentre = v ; Number of prochiral carbon = x and number of stereoisomer =

yz. Represent your answer as vxyz. For example v = 4, x = 4 and yz = 34 so represent it as
4434.

Q.13 How many geometrical isomers are possible for the following structure.

H
Q.14 Relationship between molecules:–
CH3 CH3 CH3 CH3

(a) &

C C
H H H H
H H Cl H
(b) C=C=C=C & C=C=C=C
Cl Cl H Cl
CH3 CH3 CH3 CH3

(c) &

Cl Cl

(d) CH3 & CH3

CH3 CH3
40
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(e) &

(f) &

Q.15 Calculate total no. of optical isomers, optically, active, meso & enantiomer pairs corresponding to
the following:–

(a)

41
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 organic chemistry
DPP-14 Time: 15 minutes

Q.1 Match the following :

Column I Column II
O
Me C – Me
(A) (P) Meso compound
Me Progesteron

O
Me2N
Me OH
C C – Me
(B) (Q) Compound having even no. of chiral carbon

O
(RO–486/mifepristone)
O
H
(C) O (R) Optically active compound
H
O N
H

COOH
H OH
(D) (S) Compound having odd no. of chiral carbon
H OH
COOH
(T) Compound having odd no. of prochiral carbon.

Q.2 Match the following :

Column I Column II

Et N
(A) Compound having only plane symmetry and (P) N
N
Et
Et
axis of symmetry (Consider the given chair form
only)

Me Me

(B) Compound having center of symmetry, plane of (Q)

symmetry and axis of symmetry

(C) Compound having axis of symmetry (C3) (R)

N
:

(D) Compound having C2 axis of symmetry but absence (S) 2,2,3,3-Tetramethyl butane in
of plane of symmetry staggered conformer

42
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Question No.3 to 4 (2 questions)
Questions below consist of an "Assertion" in column I and "Reason" in column II. Use the
following key to choose the appropriate answer
(A) If both " Assertion" and "Reason" are correct and "Reason" is the correct explanation of the
"Assertion".
(B) If "Assertion" and "Reason" are correct, but "Reason" is not the correct explanation of the
"Assertion".
(C) If "Assertion" is correct, but "Reason" is incorrect.
(D) If "Assertion" is incorrect, but "Reason" is correct.

Q.3 Assertion : Cyclopropane is planar while cyclobutane is non-planar.

Reason : Angle strain in cyclopropane is more than that in cyclobutane.

Et
Q.4 Assertion : Et is most stable of conformer of
Me Me Me
Me
Reason : Torsional strain and flag pole interactions cause the boat conformation to have
considerably higher energy than the chair conformation.

Q.5 Correct statement about D-mannitol (in given form) :

OH OH
HO
OH
OH OH
(A) C3 axis of symmetry (B) C2 axis of symmetry
(C) Centre of symmetry is present (D) 3-chiral centre are present

Q.6 Which of the following pair of compounds can be separated by fractional crystallisation.
D H Me Me Cl
O O O O
(A) H O–C Me and D O–C OH (B) and
Cl Cl
Me OH H H Cl
COOH COOH Me Me
Me
H OH HO H
(C) HO H and HO H (D) and
COOH COOH Me

Q.7 An unknow compound weighing 4.5 gm is dissolved in enough carbon tetrachloride to make a total
volume of 250 c.c. The observed rotation of this solution is +357.75° in a 25 cm cell using the
sodium D line. But if 4.5 gm is dissolved in 125 cc we observed rotation is +355.50°. Calculate
specific rotation for this compound. (assuming length of polarimeter tube is 1 dm)

Q.8 Identify chiral and achiral compounds from the list given below :
F
Br I Cl
F C=C=C
(a) (b) (c)
Cl
Br Cl
H
CHO NO2 SO3H H H
H OH CH3
(d) (e) (f)
H OH
CO2H SO3H NO2 CH3 CH3

43
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 Me CH3 CH3
H
Et H CH3 CH3 CO2H
(g) (h) C=C (i) N–N
Cl H H HO2C
H
Me H CH3 CH3

H3C CH3
HO2C CO2H C H
N H H C
N H C
N
(j) H5C6 C6H5 (k) C6H5 (l) O C
H5C2O2C
HO2C CO2H C
H CH3

C=C=C=C
(m)

NO2 NO2

Q.9 Calculate the specific rotations of the following samples taken at 25° using the sodium D line.
(a) 1.00 g of sample is dissolved in 20.0 mL of ethanol. Then 5.00 mL of this solution is placed in a
20.0 cm polarimeter tube. The observed rotation is 1.25° counterclockwise.
(b) 0.050 g of sample is dissolved in 2.0 mL of ethanol, and this solution is placed in a 2.0 cm
polarimeter tube. The observed rotation is clockwise 0.043°.
(c) Indicate the stereo centres in the following molecule and total number of stereomers in the
following molecule. Also draw the structures of pair of distereomers.
H
N H
N O

COOH
Q.10 Select chiral molecule out of the following list compound.
H
CH3 HOOC O
OH
HO H C=C=C C
(i) (ii) (iii) (iv) N C6H5
HO H H
O N
COOH HO2C

CO2H CH3 CH3 Cl

N=N
(v) HO2C (vi) (vii)
(Azodiformic acid) CH3 CH3

CH3 CH3
(viii) (ix)
CH3 CH3 CH3 CH3

44
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 organic chemistry
DPP-15 Time: 15 minutes
Q.1 Match the following :
Column I Column II
H
(A) H C (P) It can show geometrical isomerism
Cl

(B) H H (Q) Optically active compound

C
CH3 CH3
O O
(C) (R) Presence of odd, number of chiral carbon
NH NH

Br Br
H
(D) C=C—C–C=C (S) Resolvable compound
H HH H Br
(T) Presence of Pseudo chiral centre

Q.2 Match the following :

Column I Column II
OH OH

(A) H (P) Total number of stereoisomers is odd for the structure

CH3
O
H
H CH3
(B) (Q) Total number of stereoisomers is even for the structure
CH3 – C
CH2
CO2H
H OH
(C) H OH (R) Odd number of chiral centre
CO2H
OH
H
HO
(D) CH2NH2 (S) Even number of chiral centre
HO
(T) Optically active diastreomers possible
(U)
Question No.3 to 4 (2 questions)
Questions below consist of an "Assertion" in column I and "Reason" in column II. Use the
following key to choose the appropriate answer
(A) If both " Assertion" and "Reason" are correct and "Reason" is the correct explanation of the
"Assertion".
(B) If "Assertion" and "Reason" are correct, but "Reason" is not the correct explanation of the
"Assertion".
(C) If "Assertion" is correct, but "Reason" is incorrect.
(D) If "Assertion" is incorrect, but "Reason" is correct.

45
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 CH3 O
Q.3 Assertion : is an optically active compound.
Cl CH3
Cl
Reason : No symmetry element is present in above compound.

Q.4 Assertion : Cis form of 1, 3-dimethyl cyclohexane is more stable than its trans form.
Reason : Heat of combustion of trans form of 1,3-dimethyl cyclohexane is more compared to its cis
form.

Q.5 Which of the following Fischer projection is the enantiomer of the following molecule ?
F Br
F HO
H
H3C
Cl CH3
F F F F
H3C H H3C H H CH3 H3C H
(A) F Br (B) Br F (C) F Br (D) F Br
Cl CH3 H3C Cl H3C Cl H3C Cl
OH OH OH OH

Q.6 How many plane of symmetry are present in following compound.

(A) 2 (B) 1 (C) 0 (D) 3

Q.7 (i) The specific rotation of (S)-2-iodobutane is +15.90°.

(a) Draw the structure of (S)-2-iodobutane
(b) Predict the specific rotation of (R)-2-iodobutane
(c) Determine the percentage composition of a mixture of (R) and (S)-2iodoobutane with a
specific rotation of 7.95°.
(ii) Dextrorotatory -pinene has a specific rotation D20 = + 50°. A sample of -pinene containing
both the enantiomers was found to have a specific rotation value D20 = 30°. The percentage
of the (+) and (–) enantiomers present in the sample are, respectively.

Q.8 Consider the following six structures :

OH OH
H H
N N
(I) O (II) O

HO CH3 CH3 HO CH3 CH3

OH OH
H H
N N
(III) O (IV) O

HO CH3 CH3 HO CH3 CH3

OH OH
H H
N N
(V) O (VI) O

HO CH3 CH3 HO CH3 CH3

46
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 Establish the stereochemical relationship between : (a) I and II, (b) III and IV, (c) II and III, (d) I and
V, (e) IV and (VI)

Q.9 Select resolvable compounds

Br I NO2 SO3H

(i) (ii)
I Br SO3H NO2

N Me
(iii) Ph – S = O (iv)
CH3 Me N

.. Br
N
(v) MeCHBrCH2Me (vi) Me
Me

..
N
(vii) (viii)
Me O
H Me Cl
Me N

(ix) MeN DH2Br (x) MeCH2CHCH2Me

OH

SO3H NO2
Cl
(xi) (xii) C = C = CH2
H
SO3H NO2

47
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 organic chemistry
DPP NO- 16 Time: 15 minutes
Q.1 Find relationship between given pairs
Identical Enantiomer Diastereomer Constitutional Other
isomer

(1)
(a) (b)

OH OH OH

(2)
OH OH OH
(a) (b) (c)

(3)
CO2H CO2H
(a) (b)
H Me H H
(4)
Me H Me Me
(a) (b)
HH

(5)

(a) (b)
Me Et
H OH HO H
H OH HO H
(6) Et Me
(a) (b)

Cl Cl Cl Cl

(7)

Br Br Br Br
(a) (b)

(8)

(a) (b) 48
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 Identical Enantiomer Diastereomer Constitutional Other
isomer

OH OH

(9)

(a) (b)

(10) OH OH
O O
(a) (b)

HO
H
(11) NH2
HO COOH
(a)
OH
HOOC
OH
H NH2
(b)

(12)

(a) (b)
Cl

(13)
Cl
(a) (b)

O H Cl
(14)
H O
Cl
(a) (b)
(a) (b)
O Me
(15) S—O
O
(a)
Me
O
O—S
O
(b)
49
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 organic chemistry
DPP NO- 17 Time: 15 minutes
Q.1 Find relationship between given pairs
Identical Enantiomer Diastereomer Constitutional Other
isomer
Cl
(1) Cl

(a) (b)

(2) N N

(a) (b)
Me H Me H
O
(3) Me
H OH
O O
(a) (b)

COOH COOH
(4) H OH HO H
H OH HO H
COOEt COOEt
(a) (b)

Cl Cl Cl Cl

(5)

H Me Me H
(a) (b)

OH OH
(6)
H H
(a) (b)

H H
Me H
Br Br
(7)
H H H
(a) (b)

Me Et
(8) H OH HO H
H SH HS H
Et Me
(a) (b) 50
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 Identical Enantiomer Diastereomer Constitutional Other
isomer

Cl Cl
Cl Cl
(9)
Cl Cl
(a) (b)

O OH

(10)
N N
H
(a) (b)

(11)

(a) (b)

H H

(12)
Me H
H Me
(a) (b)

Br Cl

(13)
Cl Br
(a) (b)

(14) OH OH
HO H HO H
(a) (b)

H Cl H
Et
Cl H
(15) H Cl
Cl Et
(a) (b)

51
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 organic chemistry
DPP NO- 18 Time: 15 minutes
Q.1 Find relationship between given pairs
Identical Enantiomer Diastereomer Constitutional Other
isomer
H2C = N CH = NH
O
(1)
O
(a)
H2C = N CH = NH
O

O
(b)
O

(2) C OH

H Me
(a)
Me
C H
OH
O
(b)

COOH H
H Br Br COOH
(3) H CN H
HO
OH CN
(a) (b)

O O
(4)

Br Br
(a) (b)

Br Br Me
H
(5) H Br
H
Br H
(a) (b)

O OH
(6)
(a) (b)

52
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 Identical Enantiomer Diastereomer Constitutional Other
isomer

CH3 CH3
H OH HO H
(7)
H OH H OH
CH3 CH3
(a) (b)
CH3
H OH
HO H
CH3
(c)

(8)

(a) (b)

CO2H CO2H
H OH HO H
(9) H OH HO H
CO2H CO2H
(a) (b)

Et

(10) Me Me

Et
(a)
Me Et

Et Me
(b)

O
(11)
O
(a)
O

O
(b)

53
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 Identical Enantiomer Diastereomer Constitutional Other
isomer

N
(12) N
(a) (b)

N
(13) N
(a) (b)

Cl Br
I
(14)
Br Cl
I
(a) (b)

O O
(15)
O O
(a)
O
O
O
O
(b)
O
O
O
O
(c)

NH Me NH2

(16)

(a) (b)
NH
NH2

(c) (d)
54
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 organic chemistry
DPP NO- 19 Time: 15 minutes
Q.1 Find relationship between given pairs
Identical Enantiomer Diastereomer Constitutional Other
isomer
OH O

(1)

(a) (b)
OH

(c)
H
N N
(2)

O OH
(a) (b)

(3) OH O
(a) (b)

OH OH
(c) (d)

(4)
(a) (b) (c)
Me
N N
(5)
OH
O
(a) (b)

(6) Me — C N Me — N —
—C
(a) (b)

(7) OH
OH
(a) (b)

55
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 Identical Enantiomer Diastereomer Constitutional Other
isomer

OH H
(8)
O OH O
(a) (b)
O

O H
(c)

O O
(9)

(a) (b)

(10) CH3OH OH
(a) (b)

OH OH

(11)

CH 3
(a) (b)

Cl Cl
Cl
(12)
Cl
(a) (b)

(13) CN
CN
(a) (b)

(14) CO2H
CO2H
(a) (b)

(15)

(a) (b)

56
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 organic chemistry
DPP NO- 20 Time: 15 minutes
If there is presence of given symmetry then writes ( ) otherwise (x)
Compound P.O.S(s) C2 C3 S4 S2

(1)
N

Cl

(2)

H H
C

(3) C

C
H H

(4)

Br
CH3
(5) C
CH3
CH3

CH3

(6)
CH3

Br
Br Br
(7)
Br Br
Br

57
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 organic chemistry
DPP NO- 21 Time: 15 minutes
If there is presence of given symmetry then writes ( ) otherwise (x)
Compound P.O.S(s) C2 C3 S4 S2

(1)

(2)

(3)

(4)

Cl Cl
(5) C=C
H H
Cl H
(6) C=C
H Cl
H
Br
(7) H
Br
CO2H
H OH
(8)
HO H
CO2H

(9)

(10)

58
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 organic chemistry
DPP NO- 22 Time: 15 minutes
1. Find (m) meso compounds & optically active (a) and total stereoisomer (a + m) of following
compounds
Compound Meso (m) Active isomer (a) (a + m)

H3C CH3
(1)
H3C CH3
Br
Cl
(2)
Cl

(3)

N
H
(4)
Cl Cl
Cl Br
H3C
(5) CH3
Cl Br
O OH
Cl
(6) Cl Cl
Cl
O
HO

Cl
(7)
H3C CH3
O Cl
(8) H3C
CH3

H3C O

(9)

59
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 Compound Meso (m) Active isomer (a) (a + m)

H3C

(10) CH3

CH3

Br
(11)
Br
Br
(12)
Cl

H H
C

(13)

H3C CH3

Cl Cl

(14)
Cl
Cl Cl Cl

CH3
(15)
CH3
H 3C
H 3C

Br
H3C
(16)
HN
CH3

60
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 organic chemistry
DPP NO- 24 Time: 15 minutes
1. Find (m) meso compounds & optically active (a) and total stereoisomer (a + m) of following
compounds
Compound Meso (m) Active isomer (a) (a + m)

(1)

CH3
(2) Cl
Cl
Cl
(3) CH3
CH3
Cl
Cl
CH3
(4)
Br CH3
Br
Br Br
(5)

Br
CH3 Cl SH
H3C CH3
(6)

Cl Br
(7) H3C
CH3
CH3

H3C
(8)
Cl

61
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 organic chemistry
DPP NO- 24 Time: 15 minutes
1. Find (m) meso compounds & optically active (a) and total stereoisomer (a + m) of following
compounds
Compound Meso (m) Active isomer (a) (a + m)

(1)

Br Cl
(2)
Cl Cl
Cl
CH3
(3)
CH3
OH
HO3
(4) CH3

OH

H3C
(5) CH3
HO
Br
Cl

(6)

CH3 CH3
(7)
Cl Cl
CH3 CH3
(8)
Cl Br
O OH
Cl Cl Cl
Cl
(9) Cl
Cl Cl Cl
HO O

62
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 organic chemistry
DPP NO- 25 Time: 15 minutes

1. Find (m) meso compounds & optically active (a) and total stereoisomer (a + m) of following
compounds
Compound Meso (m) Active isomer (a) (a + m)
(1)
Cl Cl

CH3
(2)
H3C Cl
Br
CH3
(3)
CH3
CH

(4)

Cl CH

(5)

CH2
(6)
CH2

CH3
(7)
H3C
CH3 H3C
H3C
(8) CH3
CH3 H3C
Br
(9) H2C CH3
H3C CH3
(10)
HO
O OH
Cl Cl Cl
(11) Cl
Cl
Cl Cl Cl
HO O

63
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 organic chemistry
DPP NO- 26 Time: 15 minutes
1. Identify correct matching and find out the total number of chiral centre.
S.No. Compound Optically active Chiral Achiral Optically No. of
molecule molecule inactive Chiral Center

N
(1) Et

Me
C
(2) Me

(3)
H
HO COOH
O
S
(4) Me

OH
(5)
OH

OH
(6) H
H
OH
Cl
Cl
(7)

O OH
HO
(8)
HO OH
OH

64
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S.No. Compound Optically active Chiral Achiral Optically No. of
molecule molecule inactive Chiral center

Me
Cl
H
(9) H
Cl Me
H
Me O

(10) O O

O
Me
H
CH2OH

Cl Cl
(11) H H

CH2OH

(12)
Me Me
O
Cl

(13)
F Br

(14)

Me
Cl H
(15)
H Cl
Me
Br
Me
H
(16)
Br
Me
H

65
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 organic chemistry
DPP NO- 27 Time: 15 minutes
1. Identify correct matching and find out the total number of chiral centre.
S.No. Compound Optically active Chiral Achiral Optically No. of
molecule molecule inactive Chiral Center

Me

Me
(1)

Me
(2) Me

H
NO2 COOH

(3)

NO2 F
Cl Cl

(4)

F F
Me

H Cl
(5) H Cl
H Cl
Me
(6) O=C=O

H Br
(7) C C
Br H

F NO2
(8) C=C=C=C
Cl Me

66
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S.No. Compound Optically active Chiral Achiral Optically No. of
molecule molecule inactive Chiral Center

Me H
C=C=C=C
(9) H Me

H H
CO2CH2CH2O2C
(10)
CO2CH2CH2O2C
H H

CO2H H
H
(11)
OH
HO CO2H

H
CO2CH2CH2OH
(12)
CO2H
H
H CO2H
OH
(13)
OH
CO2H H

Me H

O NH
(14)
HN O

H Me

H Me

O NH
(15)
HN O

H Me

Cl Cl
H H

(16)

67
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 organic chemistry
DPP NO- 28 Time: 15 minutes
1. Identify correct matching and find out the total number of chiral centre.
S.No. Compound Optically active Chiral Achiral Optically No. of
molecule molecule inactive Chiral Center

Ph COOH

(1) H H Ph
H

COOH H
H H
(2)
Me COOH
H
(3)
COOH
Me H
F
Br
(4) F
Br
I
(5) C=C=C
Cl

(6)

Me Cl

(7)

Me

(8)

Me Me

(9)

Me Me

68
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S.No. Compound Optically Chiral Achiral Optically No. of
active molecule molecule inactive Chiral center

(10) H H

Me Me
Cl

(11)
Cl
Me Cl
Me
Br
(12) COOH
Me Me
Br Me Br OH Me Br

(13) Me Me

H Me OH Br Me H
D COOH

(14)

Me H

(15)
O
O

H N C6H5
(16) N
HO2C

CH3

H Cl
(17)
Cl H

CH3

69
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