■ Exercise-1 ]

Stereoisomerism /,...------------------------------1--

a. Marked Questions may have for Revision Questions.

PART - I : SUBJECTIVE QUESTIONS
Section (A) : Geometrical isomerism
A-1.a. Which of the following compounds have restricted rotation and out of which can show geometrical isomerism?

C l

(i)� (iii) CICH = CHCI (iv) Ph-N=N-Ph

l8,lc1
(v) CH3CH = C(CH3'2
A-2. Write the essential conditions for geometrical isomerism.
A-3. Define restricted rotation and give one example each of acyclic and cyclic compound, which can show
geometrical isomersm.
A-4. Which of the following can show geometrical isomerism.
CH,

(ii) ((
CH,

�Br
(v)
�

J>=
H
C......-
(vii) '- H3
C (viii) CH 2= CH-CH=CH-Ph
Cl

A-5.a. Which of the following carbonyl compound will give two products after reaction with NHpH:
0
0
(i) (ii) CH3-CHO (iii)
L
6
CHO
(iv)DCHO (v)>==y (vi)
A
0

Section (B) : CIP Rules (E/Z Naming) & Physical Properties of G.I
8-1. Indicate whether each of the following compound is 'E' or'Z'.
CH3'..... <(Cl I CH3 ... D H H H2 C CI

(i) /C = C "Br (ii) > C = C< (Ill) > C = C< (iv) > C = C<
H H C 3H I H D CH 3 Cl

B-2.a. (a) BrHC = CHBr exists as two diastereomers draw them and cor1pare 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?

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Stereoisomerism/,...
Section (C) : Chiral carbon and Projection Formula
C-1. Number of chiral carbon atoms in the compound w, x, y and z respectively would be:

o5
Me Me

w X y z

C-2. How many number of chiral centres present in the following compounds?

C H20H

(i) H OH o D(+)-Sucrose
HOH,C
�
H H HO
CH,OH
OH H

Section (D) : R/S & D/L Naming.

D-1. Find R/S configuration of following compounds.

COOH
H OH
(IV) +
HO H
COOH

D-2. Find D/L configuration in the following molecules.

CHO
H----rOH
(II)
H ----r OH
CH2--0H

D-3."'IS. The R/S configuration of following compounds are :

;.)I__
Cl H
(c) �f•·, (d)
I ,,, , , ,
OH
H

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Stereoisomerism /,...--------------------------------
F-3. Give the relationship between the following pairs of compounds.
Compounds Relationship
CH� /H H '-.__ /H
(a) C=C and C=C
H/ 'cH2 - CH2 - OH Hp_..-/ '----cH2 - 0- CH)

CH, Cl
Cl Cl Br
(b) and

Cl CH,

(c) � and
C'
CH3 CH,
H
0H H 0H
(d) H$Cl and Cl$ H
H OH H OH
C2H, C2H,

H, /CH3 CH3, H H, /CH3

C �

F-4.a.

CIAB, a,Ac, Cl;'.) ••,,,, Br

I II m
(i) Total number of fractions on fractional distillation of I, 11 and 111. (ii) Optical active compounds.
(iii) Relation between I and 11. (iv) Relation between I and 111.

S.ection (G): Specific rotation, optical purity, enantiomeric excess and Optical Resolution
G-1. What does D/L & dlt represent.
G-2. Write the definition of specific rotation.
G-3. Write the formula for optical purity & enantiomeric excess.
G-4.a. The total number of fractions (n) obtained in the following reaction is ......... .

l•ra,,,,., ,,.,,"''"
(n) fraction

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Stereoisomerism ,....--------------------------------
/
Section (H): Optical active compounds without chiral carbon and Amine inversion
H-1. Which of the following are chiral compound.
0 CH3
0
� £) g,,\\iiCI I �"iiH
(i) /s, (ii) (iii) N
Me Et C2H5Q/'Br Et/ ...._,D

Me CH3 H
� I
(iv) Ji•"iiH (v) c (vi)
C111111 C2Hs
Et/ 'Ph C2H/
"'-. /\
5 H H CH3

H-2.a Which of the following are chiral molecules

H>O<xBr
(i) Ph--CH=C=C=CH-CI (iii) --
Br -H
Me Br
C CI Cl Cl
(iv) >O<>O< (v) >O=C =<)< (v;)�
B Br Br Br
Cl Cl

Section (I): Calculation of no. of Stereoisomers

1-1. Find the number of geometrical isomers possible of the following compounds.
(i) � (ii) �
(iii)� �iv)�
1-2. How many n-octene can show geometrical isomerism ?
1-3. How many geometrical isomers are possible for Hepta-2, 5-dienoic acid :

1-4.a For the given compound CH3- CH - CH= CH- CH 3.

I
OH
(I) Total number of stereoisomers.
(11) Number of optically active stereoisomers.
(11l)Total number of fractions on fractional distillation of all stereoisomers.
1-5. The total number of possible isomers with molecular formula C6H 12 that contain a cyclobutane ring.

1-6. The number of isomers for the compound with molecular formula C2BrCIFI are:
Section (J) : Conformational Isomerism
J-1. Which conformational state of n-butane lies in higher energy state when rotated along C2-C 3 bond?
J-2. Draw the most stable conformation of meso-CH3CHD - CHDCH3
J-3.a. Consider all types of C-C bond rotation in following molecule.

CD 3
I
H3 C-C-CF3
I
CCl3
How many number of different types of eclipsed conformations are possible ? Draw Newman conformations

■
of all eclipsed form.

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Stereoisomerism /,....------------------------------1--
J.4_ Write the most polar and most stable conformer of 1-nitropropane.
J-5. Draw the most stable conformer of 3-hydroxypropanal.

J-6.a Write the newman projection formula of the following compounds

(I) CI-CH2-CH2-CH3 in its most polar form.
(11) HO-CH2-CH2-0H in its most stable form.
(111) HOO�H2-CH2-COOH in its least stable staggered form.
J-7. Draw the most stable newman projection formula along C 1 -C2 bonds of following compounds.
CH 3
1 2 1 21
(ii) CH,-CH-CH3 (iii) CH3-C-CH3
I I
CH3 CH 3

CH 3 CH3 OH OH
. I I 1 2 I I
( iv) CH -CH-CH-CH (v) HO-CH2-cH2-F (VI.) HOOC-CH-CH-COOH
3
3 1 2 1 2

Section (K) : Cyclohexane

K-1. 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 �v) 1e, 2a (v) 1 e, 3a (vi) 1 e, 4a (vii) 1a, 3a
K-2. Which one is more stable and why?

�
____.::,,.

Me Me
(I) (II)

PART - II : ONLY ONE OPTION CORRECT TYPE

* Marked Questions may have more than one correct option.
Section (A) : Geometrical isomerism
A-1. Stereoisomers have different :
(A) Molecular formula (B) Structural formula (C) Configuration (D) Molecular mass
A-2. Which can show the cis-trans isomerism :
(A) CICH2CH2CI (B) Cl2C=CH2 (D) CICH =CHCI
A-3. Which of the following compounds will not show geometrical isomerism :
(A) Azomethane (B) 1-Bromo-2-chloroethene (C) 1-Phenylpropene (D) 2-Methy1-2-butene
A-4.a Which of the following compound can not show geometrical isomerism?

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Stereoisomerism ,...---------------------------------1-­
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A-S.* Which of the following will form only one oxime on reaction with NH20H solution ?

0
( ) (C)dD
B Cf

Section (B) : CIP Rules (E/Z Naming) & Physical Properties of G.I
B-1. Identify (Z) - 2 - pentene :

(A)>=<-"
H H
(B)"=-.
"'-
(C) =.r (D)'\=,/

B-2. The 'E'-isomer is/are:

(A) F)c=c<
H

Cl Br
C2 .
>C =C <CH(CH,)
H H

(C)
H,C 2

B-3.a. The correct order/s for the given pair of isomers is

CH3 _.....,.CHl CH J -.....,, _.....,.H
'C=C > C=C (Melting point)
H/ '-...CH3
�)
H/ '-...H
H -.....,, _.....,.H H -.....,, _.....,.COOH
(B) C=C < C=C (Dipole moment)
HOOC/ COOH HOOC/ '-... H
........_

(Boiling point)

(Water solubility)

Section (C) : Chiral carbon and Projection Formula

C-1. Chiral molecules are:
(A) Superimposable on their mirror image
(B) Not superimposable on their mirror image
(C) unstable molecules
(D) capable of showing geometrical isomerism
C-2.a. Number of chiral carbon persent in the following compound:
CH3 -CH-CH2 -CH-CH-CH3
I I I
OH Br C2H5
2 (B)3 (C)4 (0)5
(A)
C-3. The compound which has maximum number of chiral centres is

OH OH
Cl OH OH

(A)AA (B)� ( D)a

Cl
(C)CQ

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 ------------------------------­
Stereoisomerism
/,...
Section (D) : R/S & D/L Naming.
D-1. Which of the following is the structure of (S)-Pentan-2-ol is ?

y2H s
C2Hs CH, C H3 CH2

(A) H+OH (B) H+OH (C) H+OH (D) H +OH

C2Hs C2Hs CHZ CH ,
I
C2H0
Br
I
c ..1111\'lH
D-2."a. The configuration of the given compound is:
H3C/ �Cl
(A) E (B) R (C) S (D)Z
D-3. Which Fisher projection represents the given wedge dash structure :
Br

HsC2�
�
CH
H

Br CH3 CH 3 Br

(A) H,C,+CH, (B) H,C,+B r (C)Br+H (D) H,C+C,H,

H H C2H0 H

D-4."a. Which of the following have same configuration.

Br H
�IH
I
IIICI ),,,n111Br
A
Cl Br H F F '\Cl
I II Ill
(A) I & II (B) II & Ill (C) I &Ill (D)AII
D-5. Which has D configuration.

CH3 OH CH3 COOH

H+COOH H +OH H2 +H
(A) HO+H (B) ( C) (D)
COOH CH, CHO CH,

Section (E) : Element of Symmetries (POS, COS, AOS)

E-1. Which of the following compound posses plane of symmetry?

C H3 Cl
I
(B) H,,,,,,••, -.........._C2H5
(D) □"!'--..._CH
Cl
3

Br

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Stereoisomerism /,...------------------------------1-­
E-2.a.. Which of the following compound posses centre of symmetry?

H //
0 CH3
Hx"N-CxCHl H OH ��yl
(B) (C)OH+H
H3C C-N H
(D) �

'\.H Cl H
0
//
CH3

E-3. Which of the following are chiral

CH3 ''''CI

(1)
CH�·
n
,,,ij1CH3
(2)
')-]"'

LJ.,'''''CH
4
( )
CH,
b
,.CH
3

(A)1, 2, 3 (B)1, 2, 4
3

(C)2,3,4 (D) 1,3,4

Section (F) : Definition and Properties of Enantiomers, Diastereomers, Meso compounds

F-1. Which is not the p air of enantiomers ?

+ +
COOH COOH

(A) H Cl Cl H (B) H�H HO�

CH3 CH3
C2H s C2 H5

+ +
3 3

OH

(C) Br
C2H s
H
3
Br
CH3
H
5
(D)H J: _ H
CH20H
)::
HO s H
CHO

F-2.a. Which of the following pairs of compounds are enantiomers:

CH3 CH3
H+OH HO+H
(A) H--+-OH and HO--+-H (B) an d
OH IH HI OH HOI H HO IH

CH3 CH3 CH3 CH3

+ +
H +OH H OH HO H HO�H
and (D) H IOH and
HO H H IOH HO H
(C)
I T
CH3 CH3 CH3 CH3

Stereoisomers which are not mirror image of each other, are called
(A)Enantiomers (B)Tautomers (C ) Meso (D)Diastereomers
F-3.

F-4. Which one a mong the following is not diastereomeric p air.

COOH COOH COOH COCH
H OH HO H H H H OH
+ + :+= +
H Br H Br B H B H
COOH COOH COOH COOH
(I) (11) (III) (IV)
(A)I an d Ill (B)I and II (C) II and Ill (D)I and IV

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Stereoisomerism /,...---------------------------------1-­

F-5.a.. What is the relationship between (I) & (l•I)

F Br
1--t-H c1+cH 3

Br CH3 TIH
,
Cl F
(I) (ll)

(A) Enantiomer (B) Diastereomers (C) Constitutional isomer (D) Identical molecules

(A) Enantiomers (B) Optical inactive diastereomers

(C) Optical active diastereomers (D) Identical

Sectioro (G) : Specific rotation, optical purity, enantoomeric excess and Optical Resolution
G-1. The instrument which can be used to measure optical activity, i.e., specific rotation:
(A) Refractometer (B) Photometer (C) Voltmeter (D) Polarimeter
(+) 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 wil l be :
(A) + 6 unit (B) + 12 unit (C) - 6 unit (D) + 24 unit

CH3 Cl

H Cl H CH J
G-3.-a. If optical rotation produced by is+ 36° then that produced by is
Cl H C l += H
=t=
H3 CH 3
(A) -36° (B) 0° (C) +36° (D) unpredictable
G-4. 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

G-5.a.. The racemic mixture of Alanine CH 3-yH-COOH)can be resolved by using,

( NH 2 )

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

(3) (±) -2-Butanol (4) (de mix)-2- Chlorobutanoic acid
(A) 1 & 2 only (B) 1 & 3 only (C) 2 & 4 only (D) 3 & 4 only
G-6."!9.. The major product (ester) of the following reaction is
0
Me,* 11 ,. /Me
H2so.
,•. C -C-OH + HO- C.w
H� I I '�El

(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)

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/
Stereoisomerism
G-7. 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- C H2- C H2-COOH (D) (+)-lactic acid and (- )-lactic acid
NH2

Section (H): Optical active compownds without chiral carbon and Amine inversion
H-1.*a. Which of the following compounds will show optical activity?

(A) / l'-c H
H CH 2 s
J
(B) -r-O
C H3

C 2 H0
( C)

H-2. Which of the following amine is optically active?

(D) sec-Buty1amine

H-3."ls. The following molecules are:

H3C� ,.,.,...H H ,.,.,... CH3
'��-C = = c,
%,C = C =C
H
C
H✓ '--CH3 H3C�
(A) Enantiomers (B) Oiastereomers ( C ) Identical (0) Conformers
H-4.* Which of the following is/are chiral?
Cl CI Cl CI
>OOO< B >OO=<
(A) ( ) Br Br
Br Br

Me Me
H�Br
(C)� (O)Br/vv"':..H
Et Et

Section (I): Calculation of no. of Stereoisomers

1-1. How many geomerancal isomers are possible for the given compound.
Ph - C H = C H - C H = C H - C OOH
(A)2 (8)4 ( C )6 (0)8
1-2. How many geomet�ncal isomers are possible for the given compound.
C H3 - C H = C H - C H= C H - C H = C H2
(A)2 (8)3 (C)4 (D)8
1-3. How many geomet01Ccal isomers are possible for the given compound.

C H3--o- C H = N - OH

(A)2 (8)4 (C)6 (0)8

1-4. Total number of stereoisomers of compound is :
C H3 - C H- C H- C H 3

6H �r
(A) 2 (8)4 ( C )6 (0)8

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Stereoisomerism /
1-5.a. Total number of optically active stereoisomers of tartaric acid is
(A)2 (8)4 (C) 3 (D)O
--
1-6. Number of fractions on fractional distillation of mixture of:
F F Br F
D CI H I H F H Br
+ + + +
H I 0 Cl 0 I Cl D
Br Br Cl I
(I) (II) (III) (IV)
(A)2 (8)3 (C)4 (0)1

1-7."!s. Total number of optically active stereoisollhers of CH 3 - CH- CH - CH -CH3

I I I
Cl Cl Cl
(A)2 (8)4 (C)6 (0)8
1-8.a. T he total number of ketones (including stereo isomers) with the molecular formula C6H 120 is:
(A)4 (8)5 (C)6 (0)7
1-9. Total number of optical active stereoisomers of the following compound is :
CH 3 - CH = CH - CHCI - CH = C = CH - CH = CH - CH 3
(A)8 (8)6 (C)16 (0)10
Section (J) : Conformational Isomerism
J-1. T he eclipsed and staggered conformation of ethane is due to -
(A) Free rotation about C-C single bond (8) Restricted rotation about C-C single bond
(C)Absence of rotation about C-C bond (0) None of the above
J-2. 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 (0)Attraction of opposite charges
J-3."!s. T he Baeyer's angle strain is expected to be maximum in
(A) Cyclodecane (B) Cyclopentane (C)Cyclobutane (D)Cyclopropane
J-4. The minimum torsional strain developed in butane is at dihedral angle(s)
(A) 0°, 108° (B)120•, 240 ° (C) 60•, 1 ao•, 300" (D)60•, 120•, 1 ao•
J-5. In the following the most stable conformation of n-butane is :

J-6.a. Newman projection of Butane is given, C-2 is rotated by 120° along C2-C3 bond in anticlockwise direction
the conformation formed is

pH3
H*c:H3
3 2

H H
H
(A) anti (B) fully eclipsed (C) gauche (D) partially eclipsed
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Stereoisomerism /,...-------------------------------­
J-7.'5.. Which of the following is an achira l molecule?
C H, CH C H, COOH
H,C CI Br, H H*OH H*OH
(A) * (B) * (C) (D)
Cl H Cl H,C�H
H H �OH
CH, CH,
H C OOH

J-8.& The newman projection formula of 2,3-dimethylbutane is given as

X
H CH,
�

HYH

X,Y respectively can be

(A)-CH(CH3)2 and H (B)-CH3and-C2H5 (D) H and-CH(CH)2
J-9. In 2-Fluoroethanol which conformer will be most stable ?
(A) Eclipsed (B) Skew (C) Gauche (D) Staggered
J-10. The tru e statement about the following corformation is:

Me
H*F

H OH
Me
(A) It has maximum angle strain.
(B) It does not have e clipsing stra in (tortional strain).
(C) It does not h ave any intramolecular hydrogen bonding.
(D) It has maximum vander waal strain.

COOH
HOWH OH
?OOH �
J-11.a � and
H OH � booH
are

HO H
COOH
(A) Enantiom ers (B) diastereomers (C) Identical compounds (D) Conformers

Section (K) : Cyclohexane

K-1. The least stable conformation of cyclohexane is
(A) Boat (B) Chair (C) Twist bo at (D) Half chair
K-2. Flagpole intera ction is present in
(A) Bo at form of cycloh exane (8) Ch air form of cycloh exane
(C) Anti form of n-butane (D) Fully eclips ed form of n-butane
K-3. Chair form of cyclohexane is more stable than boat form be cause :
(A) In ch air form ca rbons are in staggered form and in bo at form carbons are in eclipsed form
(8) In chair form carbons are in eclipsed form a nd in boa t form all th e carbons are in staggered form
(C) Bond angle in cha ir 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 °

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Stereoisomerism /,--------------------------------­
K-4.-a.. The most stable form of trans-1,4-dimethylcyclohexane is represented as :
CH3

(B)�
CH,
CH3
H H
( C) f �·c H, (D)� 3
v-----.......__
H

K-5. Geometry of the given compound CH,� is:

CH,�

(A) Cis (B)Trans

(C) Cis and trans both (D) No geometrical isomerism
K-6.-a.. The most stable form of cis cyclohexane-1,3-diol is represented as:
OH
(A) �OH (B)�oH
�

OH OH
O,H�
(C) � OH (D)Lt:d

PART- Ill· MATCH THIE COLUMN

1.-a.. Match the column-I with column-II
Column-I Column-II
H
O=HC
I
f OH
(A) iP) Chiral Molecule
H 1'""j---cH=O
HO

HO'{·••'' CH=O
(B) (q)Achiral Molecule
H0-¾""111 H
CH=O

(CJ O=H10H
(r) Plane or centre of symmetry present
H .i• CH=O
HO

Br

(D)
H \
I
Ph-\"" H4
Ph
(s)Axis of symmetry present (except C,).

Br

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Stereoisomerism /,...---------------------------------
2.'a. Match the following:
Column-I Column-II
OH OH
H OH H H
(A) * and * ,�p) 1 st is more stable in the given form.
H H H H
H OH
I TI
COOH COOH
H COOH H H
d
( ) * an * (q) I, 11 are conformational diastereomers.
8
H H H H
H COOH
I Il
Me Me
H H
D D
(C) * and * (r) 11nd is more stable in the given form.
H H
D D
Me Me
T IT
CHO CHO
H NH2 H H
(D) * and * (s) dipole moment of I is more than �.
H H H H
H N H2
l 11
(t) I, I� are configurational diastereomers.
3. Match the following:
Column-I Column-II

A
CH,

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

CH3 H '
CH H

jH,
( )
A (q) Conformation with maximum vander waal strain

i
8
H H H CH,

H H

(C) (r) Conformation of maximum torsional strain

CH,

H�CH,

(D) HYH (s) Conformation with minimum torsional strain

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■ Exercise-2 )
Stereoisomerism /,...------------------------------1--

a. Marked Questions may have for Revision Questions.

PART - I : ONLY ONE OPTION CORRECT TYPE
1.a. Which of the following molecule is chiral.
Cl

r., � r.,
(A)� (C) (D)
H H Br

2.a. Which one of the following compounds will show enantiomerism?

(A) CH, -0- CH3 (B) H 3C-@- CH3

3.
(C)

HO-H2 r {""\-OH

Number of conformational isomers of ethane

(D)o-OH

(A) 7 (B) 3 (C)4 (D) Infinite

4.a. Which of the following statement regarding the projections shown below is true?

H,c'rfyc1
}!
Cl�CH3 CH,
H
Cl CH,
(a)
(b)
(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
5. The structures represent

Cl H Cl
� &
H OH
H
(A) geometrical isomers (B) positional isomers
(C) conformational isomers (D) configurational isomers
6.a. The given compound (X) has:

Cl

Cl Cl
(A) chirality (B) superimposability on its mirror image isomer
(C) plane of symmetry (D) C2 axis of symmetry

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Stereoisomerism /,...-------------------------------
The compounds X and Y in below reaction can be
- H2 0
7.'a.
Ph - NH . NH2 + (X) (Y) P+Q I
organic
+
products
+
�
(A) CH3-CH2-C-CH3 CH3-C-Ph

No. of Geometrical isomers for following compound is:

CH3
8.

C:::X
CH2 - CH = CH - CH = N - OH
(A)8 (B)16 (C)32 (D) 10

cihM•
CH= NH

How many sterel»somers are poss;ble for ?

}¥Et
9.

OH
(A)128 (B)64 (C)32 (D) 16
10.'a. How many spatial orientations are possible in the following compound?
J CH=CHCH,

(A) 2 (C) 6 (0)4

CHCICH,Br
(B)8
PART - II : SINGLE AND DOUBLE VALUE INTEGER TYPE
1.'a. How many cyclic and acyclic structural isomers of C5H10 can show geometrical isomerism?
2.'a. In given compounds how many can show geometrical isomerism-

D
CH_,

(i)�
(on M
cp
(iv)O
Me Et OH
CH,

3. In given compounds how many have Z configuration along double bond?

Me3C Ph Me CH = CH2
>=<
H>=< NMe2
ro oo
H Et

1
CH3 H
F

X ""---/
(iii) (iv) �
14 NH 2
H D

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Stereoisomerism /,...--------------------------------

Cl

4. � Sum of c, & c, axis of symmetry is

Cl Cl

5. Optical rotaion data are expressed in standard way (specific rotation [n]0).
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.
6. How many of the following are cis dichlorocyclohexane.
Cl Cl
(iii) � (iv)�
�Cl Cl

I� Cl
fV r==?
(v) (W) {vii) c� 'ci (viii)
�Cl
Cl Cl Cl

7.a How many of the following are {configurational} enantionmers of {A)?

H r
B Cl

"" $
(A)
H CH3
CH 3

H
C Br
H , l Cl H�CH,
C
(p) $
Br (q)CH� (r) (s)
B H
(t)
H H�Br
CH, H c1CH3 C Cl
H3

8. 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

9.1s. P"'e (R Mandelic acid @1-COOH has specific rotation of-150. If a smaple contains 60% oflhe R
)

and 40% of its enantiomer, then [n] of this solution is.

10. Total number of geometrical isomers in the given compound are

8r=CH-IJC•CD-HC•€

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Stereoisomerism /,----------------------------------

o-
11. Total number of geometrical isomers in the given compound are :

CH=C-C=C-C=CH--0
I I I I
D H H D

12.a Total number of stereoisomers of compound CH3 - CH= CH- CH - CH= CH- CH3 are :
I
Cl

13.a. Total number of optically active stereoisomers of CH3 - CH - CH= CH - CH - CH 3 are:

I I
Cl Cl

14.a. For the compound A-CH2-CH27-A draw the newmann projection formula of all the stable conformational
isomers if µobs = 2D and Xan1I. = 0. 75 then find µgauche .(If A= NO2)

15. Total number of stereoisomers possible for the given structure excluding the configuration mentioned is :
CH 2OH

vf-�OCH,

H�H
H OH

16.a. Ob serve the compound 'M'

Cl

M-
HO
If in this compound
A OH

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

PART - Ill : ONE OR MORE THAN ONE OPTIONS CORRECT TYPE

1. 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 atoliiis.
2. Which of the following compounds has cis configuration at each double bond?
(A)� (B)�

(C) / \ \ (D)N7
/ \
3. Which of the following carbonyl compounds can give two oximes on reaction with hydroxyl amine?
(A) HCHO (B) CH3CHO (C) PhCHO (D) CH3 COPh

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Stereoisomerism /,...--------------------------------
4. Which of the following is true for maleic acid and fumaric acid.
(A) Configurational isomers (B) Stereo isomers
(C) Zand E isomers (D) Constitutional isomers
5. Which of the following is correct statement :
(A) Geometrical isorm,ers are not mirror image isomer.
(B) A compound 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.
6.a Which of the following statement(s) is/are correct for given compound:
COOH H

iQPh

H COOH
a.-truxiMic acid
(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
7. Find out correct statement/s.
(A) All chiral centers are stereogenic centers.
(B) All stereogenic centers are not chiral center.
(C) A compound may be chiral without chiral center.
(D) A compound will be chiral only if it has at least one chiral center.

8.a Which is/are not the structure of 3-Methyl butan-2-ol.

c,H .
HJ y
y r ?H
(B) (C)
�CH3 � L-1
H CH3 H H CHJ

H
�
C2H�C
/ '¾. OH

9. H111,,,,, ..c�
CH3
/ OH

Fischer projection formula of this compound can be represented as :

(D)

10.a. Which of the following compounds will have C2 axis of Syilinmetry?

Br Br

(B) F�-F (C)@l$) (0)($)

F
ef
Br Cl

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Stereoisomerism /,...--------------------------------

�H2
H3 C � H
11. + is :
'
NH?" ' CH3
H
(A) optically active molecule. (B)having plane of symmetry.
(C) having axis of symmetry. (D)having centre of symmetry
12. The correct relation between compound(s)I and II is/are
COOH

H+:� H OH

(l)H-+-OH (II)Ht OH
COOH OOCH,

(A)identical . (B)diastereomers. ( )enantiomers.

C (D)configurational isomers
13. 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.
14.a. Which of the following will show geometrical isomerism?
H H
VVv
(B)
Cl�CI
N-OH
l CI
/
(C) )C)=c '-- (D)
F Br D N-OH
HO-N

PART - IV : COM.PRl:HENSION
Read the following passage carefully and answer the questions.
Comprehension # 1
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 energy also increases. In staggered conformation
Van der Waal's and torsional strains are less so these conformations are relatively more stable.
1. Which conformation has maximum energy.

H�NO, H�H

(A) CHYH (B)MeyH

N02

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Stereoisomerism /,...--------------------------------
2. In which conformation torsional strain (rotational barrier) is minimum.

CH3 H
CH*CH3 CH3lliC H3

(A) CHYCHJ (B) HYH

CH3 CH3

H Hr+<H

(0) H
H YH
H H H

Comprehension # 2
Tartaric acid [HO2CCH(OH)C H(OH)CO2H] was an important compound in history of stereochemistry. Two
naturally occuring forms of tartaric acid are optically inactive. One optically inactive form (P) has a melting
point of 21 o-212•c and can be separated into two optically acitve forms, whereas other optically inactive form
(Q) cannot be resolved further.
3.a.. Optically inactive form Q is

(C) (0) none of these

4:a. A 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.
(0) Optically inactive due to intramoleuclar hydrogen bonding.

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■ Exercise-3 )
Stereoisomerism /,....--------------------------------

PART - I : JEE (ADVANCED) / HT-JEE PROBLEMS (PREVIOUS YEARS)

* Marked Questions may have more than one correct option.
1. An enantiomerically pure acid is treated with racemic mixture of an alcohol having one chiral carbon. The
ester formed will be : [IIT-JEE-2003(5), 2/84]
(A) Optically active mixture (B) Pure enantiomer
(C) Meso compound (D) Racemic mixture
2. A recemic mixture of(±) 2-phenylpropanoic acid on esterffication with(+) 2-butanol gives two ester. Mention
the stereochemistry of the two esters produced. [IIT-JEE-2003(M),2/60]
3. Give the Newman projection formula of the least stable staggered form of n-butane. Which of the following
reasons is the causes of its unstability? [IIT-JEE-2004, 2/60)
(i) Vander-Waal's strain (ii) Torsional strain (iii) Combination of both.
4. Newman projection of Butane is given,C-2 is rotated by 120° along C-2 & C-3 bond in anticlockwise direction
the conformation formed is : [IIT.JEE-2004, (S) 2/84]
H C
H , H

*
3 2

H H
H,
C
(A) staggered (B) fully eclipsed (C) gauche (D) partially eclipsed
5. It is given that for conformational isomers, the net dipole moment is [IIT-JEE-2005, 6/60]
µobs: r µ,X I

where �Lobs= obsereved dipole moment of the compound

µ1 = dipole moment of the stable conformational isomers
xI = mole fraction of stable conformers
for the compoundZ-CH2-CH2-Z draw the Nev.man projection formula of all the stable conformationalisomers,
if µobs = 1D, and x.n,1 = 0.82, and find �lgauche' Now draw the Newman projection formula of the most stable
conformation of mesa Y-CHD-CHD-Y
(a) If Y is CH3 (rotation about C2 - C3 bond) ib) If Y is OH (rotation about C1 - C2 bond)
6. 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, 3/162)
(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statelliilent-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.
7.* The correct statement(s) about the compound given below is (are) [IIT-JEE-2008, 4/163)

c1 H
� / C H3
H.C /�
Cl H
(A) The compound is optically active
(8) The compound possesses centre of symmetry
(C) The compound possesses plane of symmetry
(D) The compound possesses axis of symmetry

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Stereoisomerism /,...-------------------------------
8.* The correct statement(s) about the compound H3C(HO)HC-CH=CH-CH(OH)CH3 (X) is(are) :
(IIT-JEE-2009, 4/160)
(A) The total number of stereoisomers possible for Xis 6.
(B) The total number of diastereomers possible for Xis 3.
( ) If the stereochemistry about the double bond in Xis trans, the number of enantiomers possible for Xis4.
C

(D) If the stereochemistry about the double bond in Xis cis, the number of enantiomers possible for Xis2.
9. The total number of cyclic structural as well as stereo isomers possible for a compound with the molecular
formula C5H 10 is [IIT-JEE-2009, 4/160)
10.* In the Newman projection for2,2-Dimethylbutane [IIT-JEE-2010, 3/163]
X
H 3 mCH3
C

Hx;:xH

X and Y can respectively be :

(A) H and H (B) H and C2H5

11.* 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, 4/180]

'
12. The number of optically active products obtained from the complete ozonolysis of the given compound is:
CH3

CH3-CH=CH-(?--CH=CH-�-CH=CH-CH,
..
'
H

.' [IIT-JEE- 2012, 3/136]

-. -.

(A) 0 (B) 1 (C)2 (0)4

13.* Which of the given statement(s) about N, 0, Pand Q with respect to Mis (are) correct?
[IIT-JEE- 2012, 4/136]
Cl
H H

:*:
H H*OH
HO H H H�H
Cl Cl
M N p Q
(A) M and N are non-mirror image stereoisomers (B) Mand O are identical
( ) Mand Pare enantiomers
C (D) M and Q are identical

14. The total number(s) of stable conformers with non-zero dipole moment for the following compound is
(are) : [JEE(Advanced)-2014, 3/120]
Cl
Br-+-CH3
Br-+-CI
CH3
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Stereoisomerism ,...-------------------------------
/
15. The total number of stereoisomers that can exist for Mis [JEE(Advanced)-2015, 4/168]

16.* Compound(s)that on hydrogenation produce(s)optically inactive compound(s)is (are)

[JEE(Advanced)-2015, 4/168]
H Br
A)
( HC�CH
3 J

H Br

I
HC��-
2
(C) 'CH3
CH3

PART - II : JEE (MAIN)/ AIEEE PROBLEMS (PREVIOUS YEARS)

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

H
CH3 0 CHl I CH3
I II I H-Cffi I
C,Hs - CH-C3H1 CH3 - C -CH-C2H5 C,Hs - CH -C,Hs
(I) (II) (III) (IV)

it is true that
(1)All four are chiral compounds (2)Only I and 11 are chiral compounds
(3)Only Ill is a chiral compound (4) Only II and IV are chiral compounds
4. Which of the following will have a mesa-isomer also? [AIEEE 2004]
(1)2-Chlorobutane (2)2,3-Dichlorobutane
(3)2,3-Dichloropentane (4)2-Hydroxypropanoic acid
5. Amongst the following compounds, the optically acitve alkane having lowest molecular mass is
[AIEEE 2004]

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Stereoisomerism /,...-------------------------------
6. Which of the following compounds is not chiral ? [AIEEE2004]
(1) 1-Chloropentane (2) 2-Chloropentane
(3) 1-Chloro-2-methylpentane (4) 3-Chloro-2-methylpentane

7. Which type of isomerism is shown by 2,3-dichlorobutane ? [AIEEE2005]

(1) diastereomerism (2) optical-isomerism
(3) geometric-isomerism (4) structural-isomerism

8. Increasing order of stability among the three main conformations (i.e. ec!opse, anti, gauche) of 2-fluoroethanol
is [AIEEE- 2006]
(1) eclipse, gauche, anti (2) gauche, eclipse, anti
(3) eclipse, anti, gauche (4) anti, gauche, esclipse

9. Which of the following molecules is expected to rotate the plane of polarized light? [AIEEE2007, 3/120]

(4)�
SH

10. Which one of the following conformations of cyclohexane is chiral? [AIEEE-2007, 3/120]
(1) Chair (2) Boat (3) Twist boat (4) Rigid

H02 -----LC02H

The absolute configuration of �,··\ H6 �H is

1

H
11. [AIEEE2008, 3/105]
.
OH
(1) R, R (2) R, S (3) S, R (4) s, S

12. The alkene that exhibits geometrical isomerism is [AIEEE2009, 4/144]

(1) 2-methyl propene (2) 2-butene
(3) 2-methyl-2-butene (4) propene

13. The number of stereoisonihers possible for a compound of the molecular formula CH3-CH=CH-CH(OH)-Me
is: [AIEEE2009, 4/144]
(1) 2 (2)4 (3) 6 (4) 3

14. Out of the following, the alkene that exhibits optical isomerism is. [AIEEE2010, 4/144]
(1) 3-methyl-2pentene (2) 4-methyl-1-pentene
(3) 3-methyl-1-pentene (4) 2-methyl-2-pentene

15. Which of the following compound will exhibit geometrical isomerism ? [JEE(Main) 2015, 4/120]
(1) 1-Phenyl-2-butene (2) 3-Phenyl-1-butene
(3) 2-Phenyl-1-butene (4) 1, 1-Diphenyl-1-propane

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■ Answers
Stereoisomerism /,...--------------------------------

�X�RCISE - 1
PART-I
A-1. Restricted rotation present in all the options but geometircal isomersim shown by ii, iii, iv, vii.
A-2. Essential conditions for geometrical isomerism are
(1)Restricted rotation must present.
(2)Two different groups must be present on both restricted atoms.
(3)Groups responsible to show geometrical isomerism must be nearly in the same plane.
A-3. The bond across which atoms cannot rotate without breaking the bonds is called restricted rotation. e.g.
i9d
C=C, C=N, ring etc.
o e

A-4. (iii) , (iv), (vi), (vii)and (viii)

A-5. 5 (i, ii, iv, v ,vi )
(i) = E (ii)= E (iii)= E (iv)= Z

Br __........Br
'----
B-2. __........c=c........__
H II H
dipole moment : II> I
(b) Because of good packing of trans isomers.
H /CH3
'\..
C=C
H,c( '\..H
Cis-Hex-2-ene Trans-Hex-2-ene
Cis has higher boiling point due to more polarity.
C-1. W has 3, X has zero, Y has 2 and Z has only one chiral centres.

C-2. (i) H OH O =9 =8
HOH 0
:

.
�
H HO
-
CH.OH
OH H

D-1. (I)R (11)S (Ill)R (IV) (R, R)

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D-2. (I) D (11) ( 2D, 3D)
COOH

(111) Equivalent fischer projection is NH+ H and configuration L

CH3

D-3. RRRR
E-1. (i) Plane of symmetry and Centre of symmetry. (ii) Plane of symmetry.
(iii) Plane of symmetry. (iv) Plane of symmetry.
(v) Plane of symmetry and Centre of symmetry.
E-2. (i) POS present and COS, AOS absent. (ii) POS present and COS, AOS absent.
(iii) POS, AOS present and COS absent. (iv) POS, COS present and AOS present.
(v) POS present and COS,AOS absent. (vi) POS, COS and AOS absent.
CH3

+
Compound Br has a single chiral centre which has no plane of symmetry.
H
D

F-1. Enantiomeric pair= (I & ill)

Diastereomeric pairs= (I & II), (II & ill)

F-2. (I) Enantiomers (i'I) Position isomers (Ill) Identical (IV) Diastereomers
F-3. (a) functional isomers (b) Enantiomers (c) Geometrical isomers (d) Diastereomers
F-4. (i) Mixture of I, II and III give two fraction on fractional distillation.
(ii) 1, II and III all are optically active
(iii) I and II are pair of enantiomers
(iv) I and III are optical diastereomer.
G-1. D/L represent nomenclature (relative configuration) while d/t represents direction of optical rotation.

G-2. Specific rotation is the number of degrees of rotation observed if a 1-dm (10-cm) tube is used and the
compound has concentration 1 gm/ml. Thus specific rotation [a] is

,. _e_
[ a], = e X C

[a]= Specific rotation 0= observed angle of rotation (degree)

t= Pathlength (dm) C= concentration (gm/ml)
i.= wavelength (nm) t= temperature (25° C)

observed optical rotation

G-3. % Optical puri ty= optical rotation of pure enantiom er x 100

.
% EnantIomenc Id -ti x 100 = excess of one enantiomer over other
. excess= -- X 100
d+€ entire mixture

G-4. 4
H-1. i, ii, iii, iv
H-2. ii, iii, v, vi
1-1. (i) 3, (ii) 2, (iii) 2, (iv) 8

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