OC Stereoisomerism E

JEE (MAIN+ADVANCED)
STEREOISOMERISM
CONTENT
S.No Pages
1. Stereoisomerism 01 – 21
2. Exercise-1 (Subjective Questions) 22 – 25
3. Exercise-2 (Objective Questions) 26 – 38
4. Exercise-3 (Section-A) 39 – 40
5. Exercise-3 (Section-B) 41 – 44
6. Exercise-4 45
7. Exercise-5 46 – 52
8. Answer Key 53 – 55
STEREOISOMERISM
ISOMERISM
INTRODUCTION
(i) The compound which have the same molecular formula but differ in physical and chemical properties are
called as Isomer and the phenomenon is called Isomerism.
(ii) The term ‘isomer’was given by Berzellius.
(iii) The isomer was derived from Greek word meaning ‘equal or like part’ (isos= equal; meros = parts)
Isomerism
Structural Isomerism Stereoisomerism

Chain isomerism
Position isomerism
Configurational Conformational
Ring chain isomerism
Functional isomerism
Metamerism
Geometrical Optical
Tautomerism Isomerism Isomerism
STEREOISOMERISM / SPACE ISOMERISM
Compounds having same molecular formula, same connectivity and structural formula but differ due to
spatial arrangement of group or atom are said to be stereo isomers and phenomenon is termed as
stereoisomerism.
It is divided into two parts : (1) Configuration isomerism (2) Conformational isomerism
1. Configuration isomerism : Stereoisomers which are not interconvertible at room temperature are
known as configurational isomers
Configurational isomerism is further divided into two parts
(A) Geometrical isomerism
(B) Optical isomerism
GEOMETRICAL ISOMERISM
It is type of configurational isomerism which arises due to restricted rotation of atoms or groups
around a double bonded system or cyclic system.
Conditions
(i) Restricted rotation
(ii) Different functional group around system which is showing geometrical isomerism.
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STEREOISOMERISM
For example:
X Y X Y
(a) C=C (b) C=C
X Y Y X
Not showing G.I. Showing G.I.

(Because same group X and Y
present on each carbon)
Geometrical isomers are named as

(a) cis- trans isomers (b) E and Z isomers (c) Syn-anti isomers
(a) Cis- trans isomers. When like atoms or groups attached at the same side of double bonded
C-atom-called as cis. isomers. When like atoms or groups are on the opposite sides of
doubly bonded carbon, are called. trans isomers.
a a a b
C=C C=C
b b b a
cis isomers trans isomers
Cl Cl Cl H
C=C C=C
H H H Cl
cis isomer trans isomer
HOOC COOH HOOC H

C=C C=C
H H H COOH
Maleic acid Fumaric acid
(cis isomer) (trans isomer)
(b) E and Z isomers,
(i) The above system is used for derivatives of alkenes in which all the four substituents
should be different
a 
C=C
b 
(ii) Following a set of rules (Cahn - Ingold-Prelog rules) the substituents on a double
bond are assigned priorities.
(iii) The double bond is assigned the configuration E (From entgegen, the german word
for opposite) if the two groups of higher priority are on the opposite sides of the
double bond.
1 2
C=C
2 1
E form
(iv) On the other hand, the double bond is assigned the configuration Z (From zusamenn,
the German word for together) if the two groups of higher priority are on the same
side of the double bond.
STEREOISOMERISM
1 1
C=C
2 2
Z form
Priority rule : cahn, ingold & prelog proposed a sequence rule.

Rule-1 When atom or group of atom which are directly attach to the stereogenic
centre have higher atomic number will have higher proirity. Example
(2) (2)
F Cl (2) NH NO2 (1)
C=C 2
C=C
(1) I Br (1)
(1) F CH3 (2)
Z-form E-form
Rule-2 When the atomic number will be same, priority assigned on basis of atomic
weight.
(1) NH H (2)
2
C=C
(2) CH3 – CH2 D (1)
E-form
Rule-3 When both atomic number and atomic weight are same then proirity will be
decided by the next joining atom.
CH3
(1)
CH3 – CH CH3 (2)
C=C
CH3 – CH2 – CH2 CH2 – CH3
(2) (1)
(E-form)
(2) CH3 CH3

CH3
C CH2 – CH – CH3
C=C (2)
CH3
CH2 CH – CH3
(1)
(1) OH CH3
(Z-form)
Rule-4 If multiple bonded group attach to the double bonded carbon, then they are
considered in following manner.
A
C =O C –O – C  A  – C – A – C
O C A C
STEREOISOMERISM
For example :
(2) Cl – CH (1)
Ex.-1 2 CH = O
C=C
NH CH2 – OH (2)
(1) 2
(E-form)
(2) (2)
NC CH = CH2
C=C
Ex.-2 C  CH (1)
(1) CH
O (Z-form)
(c) Syn-anti isomers This type of isomerism exhibit by oximes and Azo compound. Oximes
are the compounds formed by the reactions of aldehydes or ketones with hydroxyl amine.
The products obtained have all the necessary conditions for Geometrical isomerism. i.e.
restricted rotation they can be represented by the general formula
C = O + H 2 – N – OH 
Oxime of aldehyde
and oxime of unsymmetrical
C = N – OH ketone also show
Oxime Geometrical Isomerism
Aldoximes
CH3 C H CH3 H
C
N N
OH HO
Syn form Anti form
When –OH group and H atom is same side, then it is syn form otherwise anti form
CH3 CH2 – CH2 CH2 – CH2 CH3
C C
N N
OH OH
Syn form Anti form
In unsymmetrical Ketoxime, if-OH and the alphabetically alkyl present on the same side of
double bond, then it is called as syn form and other isomer is anti form
Geometrical Isomerism in Azo compound :

Eq. Ph – N = N – Ph
Ph Ph
N N
N N
Ph Ph
Syn form Anti form
STEREOISOMERISM
Geometrical Isomerism in cyclo alkane :

In cyclic compound the rotation about C – C single bond is not free because of the regidity caused
by the presence of other carbon of the ring which keep them tightly held, thus a disubstituted cyclic
compound (having the two substitution at the separate carbon) will also show Geometrical
Isomerism.The substituents on the same side are cis-isomers while the substituents on opposite
sides represent trans-isomers.
Cl H Cl H H H H H
H
H Cl Cl Cl Cl Cl
H Cl
Trans form Trans form Cis form Cis form
No. of geometrical isomers in polyenes :

Case-1 Incase of unsymmetric alkene. If R1  R2 (R1 – CH = CH – CH = CH – R2)
no. of G.I.  2n
n  number of double bond showing geometrical isomerism
Ex.- CH 3 – CH = CH – CH = CH – CH2 – CH3

N = 2n = 22 = 4.
Case-2 Incase of symmetric alkene. If R1 = R2 (R1 – CH = CH – CH = CH – R2)
no. of G.I.  2 n 1  2P 1
n
if n is even no. then , P =
2
n 1
if n is odd no. then, P =
2
Ex.- CH3 – CH = CH – CH = CH – CH = CH – CH3
n3
3 1
here P
2
N = 22 + 21 = 6
OPTICAL ISOMERISM
Configurational isomers which are differ in their optical activity.
Optical Activity : The ability of optically active substances to cause rotation in the plane of
oscillations of polarized light is called optical activity. The substances which do not have any
interaction with plane polarized light are called optically inactive substances.
STEREOISOMERISM
Following experiment was conducted to determine the optical activity of a substance

(a) Under ordinaryconditions, the light waves oscillate in infinite number of planes passing through the line
of propagation at right angle.
(b) Plane polarized light is a light whose vibrations take place in only one of these possible planes.
(c) Ordinary light can be turned into plane polarized light by passing it through Nicol prism (made up of
calcite, a special crystalline form of CaCO3)
(d) When plane polarize light is passed through the liquid or dissolved state of such substances.
(e) The plane of oscillation gets rotated through some angle towards left or right of the original plane of
oscillations. The substances which rotate the plane of polarized light are called opticallyactive substances.
(f) The substances which rotate the plane of polarized light in the clockwise direction, i.e., towards right are
called dextrorotatory substances (Latin : dextro means right). This is indicated by putting a better d or
(+) sign before the name of the substances.
(g) The substances which rotate the plane of polarized light in the anticlockwise direction, i.e., towards left
are called leavorotatory substances (Latin : laevus means left). This is indicated by putting letter ‘ ‘ or
(–) sign before the name of the substance.
(h) The angle through which the plane of polarized light is rotated is represented by and is called observed
angle of rotation.
Polarimeter
(i) The amount of rotation caused by an optical active compound depends on various factors-
(a) Wavelength of light beam
(b) Temperature
(c) Density or concentration
(d) Length of the solution through which light beam has been passed.
Specific Rotation : The specific rotation of optically active compound can be defined as the amount
of optical rotation observed when plane polarised light is passed through a solution of 1 gm per ml
concentration solution in a 1 dm long tube.
t 
Specific rotation = [] 
l C
Cause of optical activity:-

(a) In order to exhibit optical activity, an object or molecule must be chiral.
(b) Any molecule or object is said to be chiral if does not have any element of symmetry i.e. a plane of
symmetry or a centre of symmetry.
STEREOISOMERISM
Plane of symmetry:- A 'Plane' of symmetry' is a plane which divides an object in such a way that the
part of it on one side of the plane is the mirror image of that on the other side for eg. a ball is
symmetrical while a hand is asymmetric
A chiral molecule or object is non-superimposable on its mirror images.

(c) Hence, chiral objects or molecules are also called dissymmetric objects or molecules the word chiral
in fact is derived from the Greek word cheir, meaning hard.
Chiral centre:-
(i)Acarbon atom bonded to four different atoms / groups in the molecule is called Chiral centre.
(ii) The chiral centre in the molecule is represented by asterisk (*). For example, the second carbon in
lactic acid is chiral centre because it is bonded to four different groups
(– H, – CH3, – OH and – COOH).
Chiral centre
H
CH3 – C*– COOH
OH
(iii) Some more examples of molecules having one chiral centre are
* * *
CH 3 – CH – C 2H 5 CH 3 – CH – C 2H 5 CH3CH2 CH2 – CH – C2H5
Br OH CH3
2-Bromobutane 2-Butanol 3-Methylhexane
(d) Compounds which are mirror images of each other and are not superimposable are termed
enantiomers and the phenomenon is described as enantiomerism.
Enantiomers : Enantiomers are molecules which are mirror images of each other i.e. they should be
non-superimposable.
d d
c b a a b c
Mirror
Characteristics of Enatiomers :
Some of the important characteristics of enantiomers are as given below :
(i) Enantiomers have identical physical properties such as melting point, boiling point, density, refractive
index etc.
STEREOISOMERISM
(ii) Enantiomers are optically active substances. They rotate the plane of polarized light in opposite
directions but to the equal extent.
(iii) Enantiomers have identical chemical properties. This means that they form same products as a result
of chemical combination. However, their reactivity, i.e., rates of reaction with other optically active
substances are different.
(iv) Enantiomers have different biological properties. For example (+) -sugar plays significant role in
animal metabolism. On the other (–)-sugar does not play any role in metabolism.
Representation of Enantiomers :
(a) Perspective formulae (b) Fischer Projection Formulae
(a) Perspective formulae :

(i) In this method, the four groups bonded to the chiral centre are represented by different means.
(ii)Anormal line represents the bond lying in the plane of paper.
(iii)Abroken line represents the bond going behind the plane of the paper and a solid wedge
represents the bond projected out towards the viewer.
W in the plane
below the plane
C
X Z
Y above the plane
(b) Fischer Projection Formulae
(i) Emily Fischer devised a most simple and convenient method to represent the three dimensional
arrangement of groups bonded to chiral centre.
(ii) He used the point of intersection of two perpendicular lines to represent the chiral centre.
(iii) Horizontal lines represent the bonds projected out of the plane of the paper towards viewer.
(iv) Vertical lines on the other hand, represented the bonds projected back from the plane of the
paper away from the viewer.
(v) The Fischer projection formulae of enantiomers of 2-butanol and lactic acid are as under
Chiral centre
CH3 CH3 CH3 CH3
H OH HO H H OH HO H
C2H5 C2H5 COOH COOH
Enantiomers of 2-butanol Enantiomers of lactic acid
STEREOISOMERISM
Important Points About Fischer Projection Formula :

(1) Fischer projection of a stereoisomer must not be lifted from the plane of the paper and turned over.
Such an operation would result into an arrangement which is enantiomer of the original stereoisomer.
W W
Lift and
X Z turn over Z X
Y Y
(A) Enantiomer of A
(2) Fischer’s projection can be rotated in the plane of the paper about the chiral centre through 180º or
its whole number multiple. Such an operation produces the same arrangement
W Y
Rotate in the paper
X Z plane through 180° Z X
Y W
(A) (Same as A)
(3) Fischer projection should not be turned in the plane of the paper through angle of 90º about the chiral
centre. Such an operation also produces enantiomer of the original compound.
W X
Turn through 90°
X Z in the plane of paper Y W
Y Z
(A) Enantiomer of A
(4) Keeping one group as steady, the other groups in the Fischer projection can be rotated clockwise or
anticlockwise simultaneously. Such operation would give same arrangement as the original.
W Fixed W
Clockwise movement
X Z of groups other than W Y X
Y Z
(A) (Same as A)
Diastereomers :
The stereoisomers which are non-superimposable and do not bear mirror image relationship are called
diastereomers. For Example, a compound having two asymmetric carbon atoms can have four
stereoisomers as shown below in the case of tartaric acid :
COOH COOH COOH COOH

H OH HO H HO H
H OH
HO H H OH H OH HO H
CH3 CH3 CH3 CH3

(I) (II) (III) (IV)
Mirror Mirror
One pair of enantiomers Second pair of enantiomers
STEREOISOMERISM
(I) is mirror image of (II); similarly (III) and (IV) are mirror images of each other. Thus, the four
isomers are two pairs of enantiomers. Now compare (I) with (III); they are neither superimposable
nor they are mirror images. They are called diastereomers. (I) and (IV) are also diastereomers, as
are (II) and (III) and (II) and (IV).
Characteristics of Diastereomers are :

(i) They show similar but not identical chemical properties. The rates of reactions are different.
(ii) They have different physical properties, such as melting points, boiling points, densities, solubilities,
refractive indices, etc.
(iii) They can be easily separated through fractional crystallization, fractional distillation, chromatography,
etc.
(iv) Diastereomers are also encountered in the case of geometrical isomers :

H3C CH3 H3C H
C=C C=C
H H H CH3
Cis Trans
MESO COMPOUND
(a) The compounds containing two or more chiral centres but possessing achiral molecular structure
because of having plane of symmetry, are called meso compounds.
CH3 CH2CH3
H * Br H * OH
CH2
H Br H OH
* *
CH3 CH2CH3
(2S, 3R) (2S, 4R)
Meso Compound
Plane of symmetry is represented by dotted line
(b) Meso compounds do not rotate the plane of polarized light in any direction, i.e., they are optically
inactive.
(c) This is because of achiral nature of their molecules. Because of the present of plane of symmetry the
optical rotation caused by half of the molecule is compensated by the rotation caused by the other
half.
(d) This cancellation of rotation within the molecule is referred to as internal compensation.
(e) In short, the meso compounds are optically inactive due to internal compensation.
STEREOISOMERISM
CONFIGURATION
(i) Three dimensional arrangement of groups about the chiral centre is called configuration
(ii) There are two methods for assigning configuration to a molecule :
(a) Relative method (b)Absolute method.
(1) Relative method of configuration (D, L System) :

(a) It uses D–Glyceraldehyde and L–Glyceraldehyde as the basis for the configuration determination.
(b) The stereochemical descriptor D refers to the arrangement in which – OH group attached to the
chiral centre is on the right side of Fischer projection, whereas descriptor L refers to arrangement in
which – OH group is on the left side of the Fischer projection of glyceraldehyde.
CHO CHO
H3C OH HO CH3
CH2OH CH2OH
(D) (L)
(d) This method was found suitable for the study of optically active sugars as the sugars are defined as
poly hydroxy aldehydes and ketones.
(e) Glyceraldehyde also contains hydroxy and aldehyde groups but this method cannot be used for
those molecules which do not process hydroxy aldehyde groups like CFCl BrI.
(f) If two or more than two –OH groups are present then D, L configuration is decided on basis of –OH
group of lowest chiral in the Golden rule following fischer projection
Golden Rule
usually, the Fischer projection is drawn, so that the longest carbon chain in the molecule is vertical with
he highly oxidised function at the top.
Examples :
(i) (ii) (iii)

COOH COOH COOH
H OH H OH
H OH
H OH HO H
Et CH3 Et
D-form D-form L-form
R–S system (Absolute configuration)

R  Rectus (Right)
S  Sinister (Left)
R-S nomenclature is assigned as follow :
Step-I :- By the set of sequence rule, we give the priority order of atom or group connected
through the chiral carbon.
Step-II :- If atom/group of minimum priority present on the verticle line, then
Movement of eyes in clockwise direction = R
STEREOISOMERISM
Movement of eyes in anticlockwise = S

Movement of eyes taken from 1  2  3 through Low molecular weight group (if needed)
2 3
S
1 3 1 2
R CW R ACW
4 4
Step III :- If minimum proirity group present on the horizontal line, then
clockwise rotation  S
anticlockwise rotation  R
1 1
2 4 4 3
R ACW R ACW
3 2
Example:-
COOH COOH
2 4
ACW
4 1 OH 1 Br
3
(1) H (2) NH2
R R
3 2
CH3 OH
Optical Isomerism in compound containing no chiral carbon atom

Various types of compounds belonging to this group are allenes, alkylidene cycloalkanes, spiro
compounds (spiranes) and properly substituted biphenyls.
(i) Allenes These are the organic compounds of the following general formula.
>C=C=C<
Allenes containing even number of double bonds exhibit optical isomerism provided the two groups
attached to each terminal carbon atom are
a a a x
C=C=C or C=C=C
b b b y
(ii) Alkylidene, cycloalkanes and spiro compounds :

When one or both of the double bonds in allenes are replaced by one and two rings, the resulting
systems are respectively known as alkylidene cycloalkanes and spiranes.
H3C H a CH2 CH2 a

C or
C C C
H COOH b CH2 CH2 b
1-Methyl cyclo hexylidene-4-acetic acid
(Alkylidene cycloalkane) Spiranes
STEREOISOMERISM
(iii) Biphenyls :Suitably substituted diphenyl compounds are also devoid of individual chiral carbon atom,
but the molecules are chiral due to restricted rotation around the single bond between the two
benzene nuclei and hence they must exist in two non-superimposable mirror images of each other.
COOH O2N F HOOC
NO2 HOOC COOH F
Number of optical isomers :

Case - 1 When the molecule is unsymmetrical. (It cannot be divided into two halves)
Number of d and l isomers = 2n
Number of meso form = 0
Total number of optical isomers = 2n
Where n is the number of chiral carbon atoms.
For eg. 2, 3 - Pentane diol
CH 3
|
H — C* — OH
|
H — C* — OH
| d and l isomers = 22 = 4
C 2H5
Case - 2 When the molecule is unsymmetrical, number of chiral carbon = even number
Number of d and l forms =2(n – 1)
Number of meso form =2(n/2 – 1)
Total number = addition of the above
n –1
= 2n – 1 + 2 2
For eg.: Tartaric acid
COOH
|
H — C* — OH
|
H — C* — OH
|
COOH
Number of d and l forms = 2(n/2 – 1) =2
Number of meso form = 2(2/2 – 1) =2º = 1
Total optical isomers = 3
Case- 3. When the molecule is symmetrical.
number of d and l form = 2(n – 1) – 2 (n/2 – ½)
Number of meso form = 2(n/2 – ½)

Total number of isomers = 2n–1
RACEMIC MIXTURE
(a) An equimolecular mixture of a pair of enantiomers is called racemic mixture or racemic modification.
(b) A racemic mixture is optically inactive. This is because of the fact that in equimolecular mixture of
enantiomeric pairs, the rotation caused by the molecules of one enantiomer is cancelled by the rotation
caused by the molecules of other enantiomer.
STEREOISOMERISM
(c) This type of compensation of optical rotation in a racemic mixture is referred to as external
compensation. Thus, racemic mixture becomes optically inactive because of external compensation.
(d) Representation of Racemic mixture : The racemic mixture of a particular sample is indicated by using
the prefix (d, l ) or (±). For example, racemic mixture of lactic acid is represented as (±) lactic acid.
RACEMIZATION
It is a process of conversion of an optically active compound into the racemic modification. Both (+)
and (–) forms of the compound are capable of racemizations under the influence of heat, light or
chemical reagents.
RESOLUTION
The process of separation of constituent enantiomeric forms from the racemic mixture is known as
resolution.
1. Chemical method : This is probably the best method of resolution. The racemic mixture is to combine
with another opticallyactive compound and the resulting products (salt - formation) differ in properties,
particularly in solubilityin various solvents. Byfractional crystallization from a suitable solvent, they can
be separated.
2. Mechanical method : If the d and l-forms of a substance exist in well defined crystalline forms, the
separation can be done by hand picking with the help of magnifying lens and a pair of tweezers.
3. Biochemical method : In this method, the resolution is done by use of micro-organisms, when certain
bacteria or moulds are added to a solution of a racemic mixture, they decompose one of the optically
active forms more rapidly than the other.
2. CONFORMATIONAL STEREOISOMERISMS
Different non-identical arrangement of atoms or group in a molecule that result by the rotation
about a single bond and that can easily be reconverted at room temperature are known as
conformational sterio isomers of conformers.
Conformation isomerism :
The different arrangement of atoms is space that result from the free rotation of group about C–C bond
axis are called conformers, and this phenomenon is called conformation isomerism. The basic structure
of the molecule various bond length and bond angle remain the same. There are infinite no. of conformers
of any molecule two out of them are defined as staggered and eclipsed.
Condition of conformation :
There should be three -bond present in a molecule.
Projection of Tetrahedral Carbon Atom :

Newman projection : In this method the molecule is observed along the central carbon-carbon
bond. a circle is drawn and centre of the circle represents the front carbon. the bonds of the front
carbon are drawn from the centre of the circle while the bonds at the hack carbon are drawn from
the periphery.
H
H
C-H bond of back carbon
H C-H bond of front carbon

H H H
STEREOISOMERISM
Saw horse projection : In this method, central carbon-carbon bond of the molecule is represented
by a straight line written in bond of the molecule is represented by a straight line written in slightly
tilted manner and the molecule is observed from the right side.
H
C H
H H
C
H H
Dihedral angle :– Angle between valencies of two adjacent atoms

Conformation in ethane (CH3–CH3)
H
H H H
H
H H 60°
Saw horse formula : H H
H H
H
Eclipsed Straggered
HH H
H H
60°
Newman's projection formula :
H H
H H H H
H
Eclipsed form : When H-atoms of one carbon are directly behind the other is called eclipsed form.
Staggered form : The hydrogen of two atoms are maximum distance with respect to one another.
Skew form : The different forms which exist between 0° to 60°.
Stability : The eclipsed form is less stable than staggered due to Vander Waal repulsion and torsional
strain.
Eclipsed < Skew < Staggered
Vander Waal repulsion : Repulsion between atoms or group of atoms.
Torsional strain : Bond pair-bond pair repulsion in eclipsed form.
Potential energy curve : Eec – Est = 3 Kcal / mole or 12.5 kJ / mole
Potential energy
3 Kcal
0 60° 120° 180°

Staggered Eclipsed Staggered
Rotation
STEREOISOMERISM
Conformation in propane :
HCH H HH
3 H CH3
60° 60°
H H H H H CH3
H H H H H
Eclipsed Staggered Eclipsed

Potential energy
13.8 kJ
Eec – Est = 13.8 kJ/mole

0 60° 120° 180°
Staggered Eclipsed Staggered
Rotation
Conformation in n-butane :
1 2 3 4
CH 3  CH 2  CH 2  CH 3 (C2–C3 bond rotation)
CH3 CH3
CH3 CH H CH3 H CH H H
3 3
H H H H H CH3 H H
H H H H H CH3
Partially staggered
Fully Eclipsed Partially Eclipsed Fully staggered
(Gauche form) or Anti form
CH3
CH3H
CH3 H
H H H H
CH3 H H
Partially Eclipsed Partially staggered
(Gauche form)
8Kcal
3.4Kcal
STEREOISOMERISM
Stability order : Anti form > Gauche > Partial eclipse > fully eclipsed
Exercise : (i) n-pentane (about C2–C3)

(ii) 3-methyl pentane (about C2 – C3)
Some important example :

O–H
H O–H
Ethylene glycol :
H H
H
Gauche form is most stable due to intramolecular H-bonding.
*** Z  CH 2  CH 2 Z= –OH, –NH2, –F, –CHO' –COOH, OCH3
|
OH
Gauche in all cases due to H-bonding.
Gauche effect : In a lone pair containing compound bulkier group should be placed in Gauche (60°)
from l.p.As l.p. has minimum steric repulsion.

(i) CH3CH2 NH 2
CH3 H
H H H H
N < N
H H H CH3

(ii) CH 3  CH  O H
|
CH 3
H H
CH3 H CH3 CH3
O O
>
CH3 H
Draw most stable conformation of following compound.
(i) n-pentane (C2–C3) bond rotation.
CH3
H H H H
C–C–C–C–C
H H H H
C2H5
STEREOISOMERISM
(ii) n-hexane (C2–C3) rotation

(C3–C4) rotation
CH3 C2H5
H H H H
C–C–C–C–C–C
H H H H
C3H7 C2H5
(iii) 3-methyl pentane (C2–C3)
CH3
CH3 H
C–C–C–C–C
C H H
C2H5
(iv) 3,3-dimethyl hexane (C3–C4) :
C2H5
C H H
|
CCCCCC
| CH3 CH3
C C2H5
(v) 2,2,3,4,5,5-hexamethyl hexane (C3–C4) :
C C C–C–C
| | H CH3
CCCCCC
| | | |
C C C C CH3 H
C–C–C
C
Conformation in cyclo alkane :
Baeyer's strain theory : According to Baeyer's strain theory, the amount of the strain is directly
proportional to the angle through which a valency bond has deviated from its normal position. i.e.
1
Amount of deviation d = (109° 28' – Valency angle)
2
1
in cyclopropane d = (109° 28' – 60°) = 24°44'
2
1
in cyclobutane d = (109° 28' – 90°) = 9°44'
2
1
in cyclopentane d = (109° 28' – 108°) = 0°44'
2
1
in cyclohexane d = (109° 28' – 120°) = –5°16'
2
STEREOISOMERISM
Heat of combustion :
Cyclohexane > Cyclopentane > Cyclobutane > cyclopropane
Heat of combustion per –CH2–
Cyclopropane > Cyclobutane > Cyclopentane > Cyclohexane
Orbital picture of angle strain :
C
C
C 109°28’
C
C C
In cyclopropane however, the C–C–C bond angle cannot be 109° 28' but instead must be 60°. As a
result the C-atom cannot be located to permit their sp3 orbitals to point toward each other. there is less
overlap and the bond is weaker than the usual C–C bond.
Conformation of cyclohexane : Cyclohexane exist in different form, such on chair form, boat form
twist boat form, half chair form.
Stability order : Chair form > boat form
Flag pole
hydrogen
Flag pole
hydrogen HH
H H
Boat conformation :
due to intraction between flag pole hydrogens boat conformation is unstable.

Chair form of cyclohexane :
H H
H H
Ha
He H H
H H
Newman’s projection
There are two type of hydrogen in cyclohexane:
(i) Axial hydrogen (Ha)
(ii) Equatorial hydrogen (He)
Ha Ha
He He
He
Ha He
Ha
Ha He He
Ha
Equatorial bond
Axial bond
In cyclohexane all carbon mentain tetrahedral geometryso that cyclohexane is most stable cycloalkane.
At room temperature one chair form flips to another chair form during flipping axial bonds converts to
equatorial & equatorial bonds converts to axial.
Ha
He
ring

 Ha
flippings
He
STEREOISOMERISM
K=1
Both chair form are equally stable.
Conformation of mono substituted cyclohexane :

CH3
Methyl cyclohexane
H CH3
5 6
H 1 H
3  H CH3
4
H
H
2
K>1
(1,3 – 1,5 intraction)
When methyl gropu is add axial position than their will be more 1,3 –1,5 intraction so that this conformation
will be least stable. By ring flipping methyl group occupied equatorial position so that new reverse chair
form will be more stable.
Write the orders of equilibrium constant for following equilibrium.

CH3
(i) K1
CH3
C2H5
(ii) K2
C2H5
C C
C
(iii) C
K3
C C
C
C C C
C
K4
(iv)
C C
C
order K1 < K2 < K3 < K4
As the size of alkyl group increases 1,3 – 1,5–intraction also increases, so that bulkyalkyl group preferably
occupied equatorial position.
STEREOISOMERISM
Draw most stable chair conformation of following compound.
CH3
(a) 1,2 - dimethyl cyclohexane
CH3
C2H5
C2H5
(b) 1-ethyl-2-methyl cyclohexane CH3
CH3
Unstable Stable
CH 3
CH3
(c) 1,3,5-trimethyl cyclohexane
CH3
CH3 CH3
CH3
(d) 1,2,3,4,5,6-hexa methyl cyclohexane CH3
CH3 CH3
C2 H 5
(e) 1-ethyl-2,3-dimethyl cyclohexane.
CH 3 CH3
STEREOISOMERISM
EXERCISE-1 (Subjective Questions)
Q.1 How many pair(s) of geometrical isomers are possible with C6H12 (only in open chain structures)
Br
Q.2 How many geometrical isomers are possible by

Br Br
Br
Q.3 Considering rotation about the C-3 – C-4 bond of 2-methylhexane:

(a) Draw the Newman projection of the most stable conformer.
(b) Draw the Newman projection of the least stable conformer.
Q.4 Assign the priority order number to the following atoms or groups.
(a) –CHO, –CH2OH, –CH3 , –OH
(b) –Ph, –CH(Me)2, –H, –NH2
(c) –COOH, –Ph , –CHO, –CH = CH2
(d) –CH(Me)2, –CH=CH2, –CCH, –Ph
(e) –CH3, –CH2Br, –CH2OH, –CH3Cl
(f) –H, –N (Me)2, –Me, –OMe
(g) –CH = CH2, –Me, – Ph, –Et
(h) –CH2–CH2–Br, –Cl, –CH2–CH2–CH2–Br, (Me)2CH–
(i) –Cl, –Br, –I, –NH2
(j) NH2 , NO2 , CH2NH2 , CN
Q.5 Write the structure of :

(i) (E) penta-1,3-diene (ii) (2Z, 4E)hexa-2,4-diene
(iii) (2E, 4E)-3-ethylhexa-2,4-diene (iv) (R)-2-Bromopentane
(v) (S)-3-bromo-3-chlorohexane (vi) (2S, 3R)-2,3-dibromobutane
Q.6 Write the E / Z configuration of each compound.

F Br O2 N CH2–CH3
C=C C=C
(i) (ii)
H3 C O–CH3 H3C–NH CH3
Cl
Et Br CH2–CH3
(iii) C=C (iv) C=C
Me CH2–I Cl CH=CH2
BANSAL CLASSES Private Ltd. ‘Bansal Tower’, A-10, Road No.-1, I.P.I.A., Kota-05, Tel.(0744) 2791000 Page # 22
STEREOISOMERISM
Q.7 Draw the two chair conformers of each compound and indicate which conformer is more stable.
(a) cis-1-ethyl-3-methylcyclohexane
(b) trans-1-ethyl-2-isopropylcyclohexane
(c) trans-1-ethyl-2-methylcyclohexane
(d) trans-1-ethyl-3-methylcyclohexane
(e) cis-1-ethyl-3- isopropylcyclohexane
(f) cis-1-ethyl-4-isopropylcyclohexane
Q.8 Write the configuration of each compound?

Cl
Cl Br Br
(i) (ii) (iii) Br (iv) Br
Cl
Cl
Q.9 Draw the most stable conformer of N-methylpiperidine.
Q.10 How many monochlorinated products of methyl cyclohexane are optically active.
Q.11 How many enantiomers are possible on monochlorination of isopentane.
Q.12 Calculate the total number of chiral carbon atoms in.

CH3 H3C CH3
H3C H3C
C=O
H CH3
H H3C H
H3C H
HO H H
(i) H H (ii)
O H Cholesterol
Progesterone (important component of membranes:
(human female sex hormone) principal component of gallstones)
CH2OH
H3C OH
H3C C=O
O H3 C H H
H3 C H OH
H H
(iii) H H (iv)
O
O Testosterone
Cortisone (human male sex hormone)
(antiinflammatory hormone)
STEREOISOMERISM
Q.13 In what stereoisomeric forms would you expect the following compounds to exist?
(a) EtCH(CO2H)Me (b) MeCH(CO2Et)CO2H
(c) (d)
(e) (f) Et(Me)C=C=C(Me)Et
(g) (h)
(i) (j)
(k)
Q.14 How many stereocenter and pseudochirality center present in the following compound?
O O
H2N NH2
O O
Q.15 Calculate the total number of stereoisomers in the following compounds.
(I) (II) (III)
Q.16 The number of stereoisomers (excluding enantiomers) for

1-bromo-2-chloro-3-iodocyclopropane
STEREOISOMERISM
Q.17 Calculate the total number of stereoisomers possible for
H CH = CH – CH3
(i) (ii) C=C=C
Cl CH = CH – CH3
OH
HO OH
Q.18 How many stereoisomers are possible for Inositol,
HO OH
OH
Q.19 Comment on the relationship among the following compounds.
(I) (II) (III) (IV)
Q.20 When 20 gm optically active compound is placed in a 10 dm tube, in a 200 ml solution rotates the
PPL by 30°.
(a) What is the angle of rotation if above solution is diluted to 1 Litre?
(b) What is the specific angle of rotation if above solution is diluted to 1 Litre?
Write answer of part (a) and (b) in the same order and present the four digit number as answer
in OMR sheet. For example : If ans of (a) is 9 and (b) is 99 then fill 0999 in OMR sheet.
STEREOISOMERISM
EXERCISE-2 (Objective Questions)

[SINGLE CORRECT CHOICE TYPE]
Q.1 How many minimum no. of C-atoms are required for position & geometrical isomerism in alkene?
(A) 4, 3 (B) 4, 4 (C) 3, 4 (D) 3, 3
O O
Cl C—O C—O Cl
Q.2 H and CH3
C=C C=C
H CH3 H H
Shows which type of isomerism
(A) Functional group isomerism (B) Geometrical isomerism
(C) Metamerism (D) Position isomerism
Q.3 Which of the following does not show geometrical isomerism?

(A) 1, 2-dichloro-1-pentene (B) 1, 3-dichloro-2-pentene
(C) 1, 1-dichloro-1-pentene (D) 1, 4-dichloro-2-pentene
Q.4 Which of the following will not show geometrical isomerism?
Me Me
(A) (B) (C) Cl (D)
Me
Q.5 Geometrical isomerism is possible in:

(A) isobutene (B) acetone oxime
(C) acetophenone oxime (D) benzophenone oxime
Q.6 Which of the following will show geometrical isomerism?
(A) (B) (C) (D)
Q.7 Which of the following will show geometrical isomerism?

Me Br
(A) (B)
Br Me
Me
(C) (D)
Br
STEREOISOMERISM
Q.8 Total number of geometrical isomer of following compound is:
(A) 2 (B) 3 (C) 4 (D) 5
Q.9 Tautomer of which compound can show geometrical isomerism ?

O
N=O NO2
(A) (B) (C) (D)
O Et
Q.10 What characteristic is the best common to both cis-2-butene and trans-2-butene?
(A) B.P. (B) Dipole moment
(C) heat of hydrogenation (D) Product of hydrogenation
Q.11 The number of cis-trans isomer possible for the following compound
(A) 2 (B) 4 (C) 6 (D) 8
Q.12 Which of the following have zero dipole moment?

(A) benzene 1,4- diol (B) trans-1,2-dichloro ethene
(C) cis-1,2-dichloro ethene (D) 1,1-dichloro ethene
Q.13 Increasing order of stability among the three main conformation (i.e. eclipse, anti, gauche) of
ethylene glycol is :
(A) Eclipse, gauche, anti (B) Gauche, eclipse, anti
(C) Eclipse, anti, gauche (D) Anti, gauche, eclipse
Q.14 Which of the followings is most stable conformation of 3-Hydroxy propanal ?

CHO CHO CHO CHO
H H OH HO H H H
(A) (B) (C) (D)

H H H H H H H OH
OH H H H H
Q.15 How many stereoisomers can exist for the following acid
H  C(OH).CO 2 H
|
H  C.CO 2 H
|
H  C(OH).CO 2 H
(A) Two (B) Four (C) Eight (D) Sixteen
STEREOISOMERISM
Q.16 Which of the following have asymmetric carbon atom?
C l Br H Cl H Cl H H
| | | | | | | |
(A) H  C  C  H (B) H  C  C  C l (C) H  C  C  H (D) H  C  C  CH 3
| | | | | | | |
H H H H H H Br OH
Q.17 The number of optically active compounds in the isomers of C4H9Br is

(A) 1 (B) 2 (C) 3 (D) 4
Q.18 The number of optically active isomers observed in 2,3-dichlorobutane is:

(A) 0 (B) 2 (C) 3 (D) 4
Q.19 The total number of isomeric optically active monochloro derivative of isopentane is:
(A) two (B) three (C) four (D) one
Q.20 Select the optically active compound among the following :
NH H3C COOH
(A) HN (B) H3C COOH
H3C CH3 HN NH
(C) HOOC COOH (D) OC CO
Q.21 How many stereoisomers of the following molecule are possible?

HOOC.CH=C=CH.COOH
(A) two optical isomers (B) two geometrical isomers
(C)two optical and two geometrical isomers (D) None
Q.22 Which of the following is not chiral ?

OH
Me COOH HO OH
(A) (B)
HO OH
HOOC Me
OH
Cl F
(C) H3C – CH = C = C = C= CH–CH3 (D)
F Cl
STEREOISOMERISM
Q.23 Which species exhibits a plane of symmetry?
(A) (B)
(C) (D)
Q.24 Which of the following has centre of symmetry?

H
F Cl H Br
C
(A) H (B) (C) (D) PCl5
H
H F Br H Cl
Q.25 Which of the following will not show optical isomerism?

(A) Cl–CH=C=C=CH–Cl (B) Cl–CH=C=C=C=CH–Cl
(C) (D)
Q.26 Meso-tartaric acid and d-tartaric acid are

(A) positional isomers(B) enantiomers (C) diastereomers (D) racemic mixture
Q.27 The structures shown here are related as being:
H Br
CH3 Br
CH3 CH3 CH3

H
Br H Br H
(I) (II)
(A) conformers (B) enantiomers
(C) geometrical isomers (D) diastereoisomers
Me
H
Me
Br Me
Q.28 What is relationship between and Me
O
H
Br
O
(A) Diastereomer (B) Enantiomer (C) Conformer (D) None of these
STEREOISOMERISM
Q.29 What is relationship between

CH2CH3 Et
Et Br H3C CH2CH3
and
Me Br
(A) Enantiomer (B) Identical (C) Diastereomer (D) Epimer
Q.30 The two compounds given below are
(A) enantiomers (B) identical (C) optically inactive (D) diastereomers
Q.31 Which of the following is incorrectly matched?
(A) Enantiomer
H 3C H H CH3
(B) Enantiomer
H CH3
CH3 H
(C) H H3C Identical
CH3 H
Br Br
(D) Identical
Br Br
Q.32 Which of the following combinations amongst the four Fischer projections represents the same
absolute configurations?
(A) (II) and (III) (B) (I) and (IV) (C) (II) and (IV) (D) (III) and (IV)
STEREOISOMERISM
Q.33
L -form of the given compound is :

CHO CHO CHO CHO
H OH HO H H OH HO H
H OH HO H HO H HO H
(A) HO H (B) H OH (C) HO H (D) HO H
CH2OH CH2OH CH2OH CH2OH
Q.34 Which of the following compound has D-configuration ?
CHO CH2OH
H OH H OH
H OH H OH
(A) HO H (B) HO H
HOH2C OH H OH
H CHO
CHO H
H OH HO CH2OH
HO H H OH
(C) H OH (D) HO H
HO CH2OH H OH
H CHO
Q.35 Number of possible stereoisomers of glucose are
(A) 10 (B) 14 (C) 16 (D) 20
Q.36 The S-ibuprofen is responsible for its pain reliveing property. Which one of the structure shown is
S-ibuprofen.
O
Me C–OH
Me C Me H
(A) (B)
CH3 Me C
H C – OH
CH3 O
CH3 O
Me ||
Me C – OH
Me C H
(C) (D) Me C H
C – OH
O CH3
STEREOISOMERISM
Q.37
The compound with the above configuration is called:

(A) (2S, 3S)-2-chloro-3-pentanol (B) (2S, 3R)-2-chloro-3-pentanol
(C) (2R, 3R)-2-chloro-3-pentanol (D) (2R, 3S)-2-chloro-3-pentanol
Q.38 The full name of the compound is
(A) (2R,3R)-3-chloro-2-pentanol (B) (2R,3S)-3-chloro-2-pentanol

(C) (2S,3R)-3-chloro-2-pentanol (D) (2S,3S)-3-chloro-2-pentanol
Q.39 The R/S configuration of these compounds are respectively.

HO H
CF3 H NH2 H CH3
HS CHO
COOH
(A) R,R,R (B) R,S,R (C) R,S,S (D) S,S,S
[ONE OR MORE THAN ONE CORRECT CHOICE TYPE]
Q.40 Which of the following statements is/are not correct?

(A) Metamerism belongs to the category of structural isomerism
(B) Tautomeric structures are the resonating structures of a molecule
(C) Keto form is always more stable than the enol form
(D) Geometrical isomerism is shown only by alkenes
Q.41 Tautomer of which of the following can show geometrical isomerism
(A) CH3–CHO (B) CH3CH2–CHO

O
O
(C) (D)
Q.42 Which will form geometrical isomers ?

Cl
(A) (B) CH3CH NOH (C) (D) All of these
Cl
STEREOISOMERISM
Q.43 Which will show geometrical isomerism ?

Me Me Me Me
(A) CH3CH NOH (B)

Et Me Me Et
H3C
(C) H C C NOH (D) HO—N N—OH
3
Q.44 The isomerism observed in alkanes is :

(A) metamerism (B) chain isomerism
(C) position isomerism (D) geometrical isomerism
Q.45 Which of the following compound can form geometrically isomeric oxime on reaction with NH2OH
O
O
(A) (B) (C) (D)
O O
Q.46 Which of the following can exist in 'syn' and 'anti' form ?
(A) C6H5—N N—OH (B) C6H5—N N—C6H5
(C) C6H5—CH N—OH (D) (C6H5)2C N—OH
Q.47 Which of the following have zero dipole moment?

(A) p-Dichlorobenzene (B) Benzene-1, 4-diol
(C) Fumaric acid (D) Maleic acid
Q.48 The Z-isomer among the following are :

(A) CH3—C—H (B) CH3—C—H
C3H7—C—C2H5 C2H5—C—C3H7
(C) Cl—C—Br (D) Cl—C—Br
H—C—F F—C—H
Q.49 The IUPAC name of the compound :
(A) (2E, 4E, 6Z)-octa-2,4,6-triene (B) (2E, 4E, 6E)-octa-2,4,6-triene

(C) (2Z, 4E, 6Z)-octa-2,4,6-triene (D) (2Z, 4Z, 6Z)-octa-2,4,6-triene
Q.50 Which of the following compound has E configuration?
H Cl
CHO CH2OH CHO
(A) H (B) NH2 (C) Cl (D) H
Br
STEREOISOMERISM
Q.51 Which of the following will show optical isomerism as well as geometrical isomerism.
(A) (B)
(C) (D)
Q.52 Which of the following statements is/are correct?

(A) A meso compound has chiral centres but exhibits no optical activity
(B) A meso compound has no chiral centres and thus are optically inactive.
(C) A meso compound has molecules which are superimposable on their mirror images even
though they contain chiral centres
(D) Ameso compound is optically inactive because the rotation caused by any molecule is cancelled
by an equal and opposite rotation caused by another molecule that is the mirror image of the first.
Q.53 Which of the following statements are correct?

(A) Any chiral compound with a single asymmetric carbon must have a positive optical rotation
if the compound has the R configuration
(B) If a structure has no plane of symmetry it is chiral
(C) All asymmetric carbons are stereocentres.
(D) Alcohol and ether are functional iosmers
Q.54 Which of the following compounds are optically active?

(A) CH3.CHOH.CH2.CH3 (B) H2C=CH.CH2.CH=CH2
HOOC NO2
(C) (D)
NO2 COOH
Q.55 Which out of the following are resolvable pair?
N + en
(A) T (B) + en
H
D
O Me
P + en
(C) Me Ph (D) Et NH2 + en
Et
H
STEREOISOMERISM
Q.56 Which of the following is/are resolvable pair?
Me
O 
(A) + en (B) N + en
Et D
H
(C) N + en (D) S + en
D Me O Et
Et Me
Q.57 Which conformation of n-Butane has both plane of symmetry and centre of symmetry absent ?
(A) fully eclipsed (B) Gauche (C) Partially eclipsed (D) Anti
Q.58 Which of the following operations on the Fischer formula does not change its absolute
configuration?
(A) Exchanging groups across the horizontal bond
(B) Exchanging groups across the vertical bond
(C) Exchanging groups across the horizontal bond and also across the vertical bond
(D) Exchanging a vertical and horizontal group
Q.59 Which of the following pairs of compound is/are identical?
(A) (B)
(C) (D)
Q.60 Concider the following structure and pick by the right statement :
H O
NH2 C
F OH
C C
H CH2OCH3
H CH2OCH3
CH3 OH III
I II
(A) I and II have R-configuration (B) I and III have R-configuration
(C) only III has S-configuration (D) I and III have S-configuration
STEREOISOMERISM
Q.61 Which of the following is a 'threo' isomer?

CHO CH3 COOH
COOH
H OH Br H H Cl
NH2
(A) H OH (B) H OH (C) H OH (D) H
H OH
CH2OH CH3 CH3
CH3
Q.62 Which of the following statements is/are not correct for D-(+) glyceraldehyde?
(A) The symbol D indicates the dextrorotatory nature of the compound
(B) The sign (+) indicates the dextrorotatory nature of the compound
(C) The symbol D indicates that hydrogen atom lies left to the chiral centre in the Fischer projection
diagram
(D) The symbol D indicates that hydrogen atom lies right to the chiral centre in the Fischer
projection diagram
Q.63 Which of the following are correct representation of L–amino acids?
(A) (B)
(C) (D)
Q.64 Which of the following are D sugars:
(A) (B)
(C) (D)
STEREOISOMERISM
[MATCH THE COLUMN]

Q.65 Column I Column II
(A) (P) Position isomers
(B) (Q) Geometrical isomers
Me OH Me
C=N C=N
(C) OH (R) First is E and second is Z form
OH OH
(D) (S) Structural isomer
OH
OH

Compound Total number of stereoisomer
(A) (P) 2
(B) (Q) 4
(C) (R) 6
(D) (S) 8
STEREOISOMERISM
CH3 CH3
Cl H Cl H
(A) H OH & HO H (P) Identical
H Cl H Cl
CH3 CH3
Me H
HS H Et SH
(B) H OH & Me H (Q) Diastereomers
Et OH
H2C Et H2C Me
(C) C CH & C CH (R) Conformer
H Me H Et
Cl H H Cl
H Cl H H
(D) & (S) Positional
H H H H
H H Cl H
Q.68 Match List-I, List-II & List-III :
List-I List-II List-III
CH3 H
CH3
Br H
HO C–C H
(a) HO H (1) (i) (2R, 3R)
CH3 CH3 Br
CH3 H
CH3
HO H
(b) Br H (2) Br C–C OH (ii) (2S,3S)
CH3 H CH3
CH3 H
CH3
H OH
C–C
(c) Br H (3) HO Br
(iii) (2S,3R)
CH3
CH3 H
CH3 H
CH3
HO H
(d) H Br (4) Br C–C OH
(iv) (2R, 3S)
CH3
CH3 H

Compound (Open chain) Number of optically active isomer
(A) Unsymmetrical compound with ‘n’ chiral carbon (P) 2n–1
(B) Symmetrical molecule with ‘n’ chiral carbon when n is even (Q) 2n–1 – 2n–1/2
(C) Symmetrical molecule with ‘n’ chiral carbon when n is odd (R) 2n
S TE R E OI S OM E R IS M
EXERCISE-3
SECTION-A
(JEE Main Previous Year's Questions)
Q.1 Stereo - Isomerism includes - [AIEEE-2002]
(A) Geometrical isomerism only (B) Optical isomerism only
(C) Both geometrical & optical isomerism (D) Position & Functional isomerism
Q.2 Which of the following does not show geometrical isomerism - [AIEEE-2002]
(A) CH3 – CH = CH – CH3 (B) CH3 – CH2 – HC = CH2
(C) CH3 – C  CH – CH3 (D) ClHC = CH – CH2 – CH3
|
Cl
Q.3 Racemic mixture is formed by mixing two – [AIEEE-2002]
(A) Isomeric compounds (B) Chiral compounds
(C) Meso compounds (D) Enanitiomers with chiral carbon
Q.4 Geometrical isomerism is not shown by – [AIEEE-2002]

(A) 1, 1– dichloro–1–pentene (B) 1, 2– dichloro–1–pentene
(C) 1, 3– dichloro–2–pentene (D) 1, 4– dichloro–2–pentene
Q.5 Among the following four structures I to IV

CH3 O CH3
(i) C2H5–CH–C3H7 (ii) C2H5 – C – CH – C2H5
H CH3
(iii) H–C–CH3 (iv) C2H5–CH–C2H5
H
It is true that – [AIEEE-2003]
(A) Only (iii) is a chiral compound (B) Only (ii) and (iv) are chiral compounds
(C)All four are chiral compounds (D) Only (i) and (ii) are chiral compounds
Q.6 Which of the following compounds is not chiral ? [AIEEE-2004]

(A) 1 – chloropentane (B) 2 – chloropentane
(C) 1 – chloro –2–methyl pentane (D) 3 – chloro – 2 – methyl pentane
Q.7 Which of the following will have a mesoisomer also - [AIEEE-2004]

(A) 2 - Chlorobutane (B) 2, 3 - Dichlorobutane
(C) 2,3 - Dichloropentane (D) 2-Hydroxypropanoic acid
Q.8 Which types of isomerism is shown by 2,3–dichlorobutane ? [AIEEE-2005]

(A) Optical (B) Diastereo (C) Structural (D) Geometric
Q.9 Increasing order of stability among the three main conformations (i.e. Eclipse, Anti, Gauche) of
2-fluoroethanol is [AIEEE 2006]
(A) Gauche, Eclipse,Anti (B) Eclipse,Anti, Gauche
(C)Anti, Gauche, Eclipse (D) Eclipse, Gauche,Anti
Q.10 Which of the following molecules is expected to rotate the plane of plane-polarised light?
[AIEEE-2007]
COOH
(A) (B) (C) (D) H2N H
Q.11 Which one of the following conformations of cyclohexane is chiral ? [AIEEE-2007]

(A) Twist boat (B) Rigid (C) Chair (D) Boat
HO2C CO2H
Q.12 The absolute configuration of is [AIEEE-2008]
OH
HO H H
(A) R, R (B) R, S (C) S, R (D) S, S
Q.13 Out of the following, the alkene that exhibits optical isomerism is [AIEEE-2010]
(A) 3-methyl-1-pentene (B) 2-methyl-2-pentene
(C) 3-methyl-2-pentene (D) 4-methyl-1-pentene
Q.14 Identify the compound that exhibits tautomerism. [AIEEE-2011]
(A) 2-Butene (B) Lactic acid (C) 2-Pentanone (D) Phenol
Q.15 How many chiral compounds are possible on monochlorination of 2-methyl butane ? [AIEEE-2012]
(A) 4 (B) 6 (C) 8 (D) 2
Q.16 For which of the following molecule significant µ  0? [JEE Main 2014]
Cl CN OH SH
(a) (b) (c) (d)
Cl CN OH SH
(A) (a) and (b) (B) only (c) (C) (c) and (d) (D) only (a)
Q.17 Which of the following compounds will exhibit geometrical isomerism? [JEE Main 2015]
(A) 2 -Phenyl -1 -butene (B) 1, 1 -Diphenyl -1 -propane
(C) 1 -Phenyl -2 -butene (D) 3 -Phenyl -1 -butene
Q.18 The absolute configuration of [JEE Main 2016]
CO2H
H OH
H Cl
CH3
is :
(A) (2R,3R) (B) (2R, 3S) (C) (2S,3R) (D) (2S, 3S)
SECTION-B
(JEE ADVANCED Previous Year's Questions)
Q.1 True or False:
2, 3, 4-Trichloropentane has three asymmetric carbon atoms. [JEE 1990]
Q.2 Isomers which can be interconverted through rotation around a single bond are [JEE 1992]
(A) Conformers (B) Diastereomers (C) Enantiomers (D) Positional isomers
Q.3 The optically active tartaric acid is named as D–(+)–tartaric acid because it has a positive
(A) optical rotation and is derived from D-glucose
(B) pH in organic solvent
(C) optical rotation and is derived from D–(+)–glyceraldehyde
(D) optical rotation only when substituted by deuterium [JEE 1992]
Q.4 The molecules that will have dipole moment are : [JEE 1992]
(A) 2,2-dimethyl propane (B) trans 2-pentene
(C) cis 3-hexene (D) 2,2,3,3-tetramethyl butane
Q.5 The shows: [JEE 1995(Scr.)]
(A) geometrical isomerism (B) optical isomerism

(C) geometrical & optical isomerism (D) tautomerism
Q.6 How many optically active stereoisomers are possible for butane-2,3-diol? [JEE 1997]
(A) 1 (B) 2 (C) 3 (D) 4
Q.7 The number of possible enantiomeric pairs that can be produced during monochlorination of 2-methyl
butane is [JEE 1997]
(A) 2 (B) 3 (C) 4 (D) 1
Q.8 When cyclohexane is poured on water, it floats, because: [JEE 1997]

(A) cyclohexane is in 'boat' form (B) cyclohexane is in 'chair' form
(C) cyclohexane is in 'crown' form (D) cyclohexane is less dense than water
Q.9 Which of the following compounds will show geometrical isomerism? [JEE 1998]
(A) 2-butene (B) propene (C) 1-phenylpropene (D) 2-methyl-2-butene
Q.10 Identify the pairs of enantiomers and diastereomers from the following compounds I, II and III.
[JEE 2000]
Q.11 Which of the following compounds will exhibit geometrical isomerism? [JEE 2000 (Scr.)]
(A) 1-Phenyl-2-butene (B) 3-Phenyl-1-butene
(C) 2-Phenyl-1-butene (D) 1,1-Diphenyl-1-propene
Q.12 The number of isomers for the compound with molecular formula C2BrClFI is
(A) 3 (B) 4 (C) 5 (D) 6 [JEE 2001 (Scr.)]
Q.13 Which of the following compounds exhibits stereoisomerism? [JEE 2002 (Scr.)]
(A) 2-methylbutene-1 (B) 3-methylbutyne-1
(C) 3-methylbutanoic acid (D) 2-methylbutanoic acid
Q.14 Which of the following hydrocarbons has the lowest dipole moment? [JEE 2002]
(A) cis-2-butene (B) 2-butyne (C) 1-butyne (D) H2C = CH – C  CH
Q.15 In the given conformation, if C2 is rotated about C2–C3 bond anticlockwise by an angle of 120° then
the conformation obtained is [JEE 2004 (Scr.)]
(A) fullyeclisped conformation (B) partiallyeclipsed conformation

(C) gauche conformation (D) staggered conformation
Q.16 On monochlorination of 2-methylbutane, the total number of chiral compounds formed is

(A) 2 (B) 4 (C) 6 (D) 8 [JEE 2004]
Q.17 (i) obs =  i x i

i
where i is the dipole moment of a stable conformer of the molecule, Z–CH2–CH2–Z and
xi is the mole fraction of the stable conformer.
Given : obs = 1.0 D and x (Anti) = 0.82
Draw all the stable conformers of Z–CH2–CH2–Z and calculate the value of (Gauche).
(ii) Draw the stable conformer of Y–CHD–CHD–Y(meso form), when Y= CH3 (rotation
about C2–C3) and Y = OH (rotation about C1 – C2 ) in Newmann projection. [JEE 2005]
Q.18 The number of structural isomers for C6H14 is [JEE 2007]

(A) 3 (B) 4 (C) 5 (D) 6
Q.19 Statement-1 : Molecules that are not superimposable on their mirror images are chiral.
because
Statement-2 : All chiral molecules have chiral centres.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-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. [JEE 2007]
Q.20 The correct statement(s) about the compound given below is (are) [JEE 2008]
Cl H
CH3
H3C
Cl H
(A) The compound is optically active
(B) The compound possesses centre of symmetry
(C) The compound possesses plane of symmetry
(D) The compound possesses axis of symmetry
Q.21 The correct statement(s) concerning the structures E, F and G is (are) [JEE 2008]
H3C O H3C OH H3C CH3
H3C CH3 H3C CH3 H3C OH

(E) (F) (G)
(A) E, F and G are resonance structures (B) E, F and E, G are tautomers
(C) F and G are geometrical isomers (D) F and G are diastereomers
Q.22 The total number of cyclic structural as well as stereo isomers possible for a compound with the molecular
formula C5H10 is [JEE 2009]
Q.23 The correct statement(s) about the compound H3C(HO) HC – CH = CH – CH (OH) CH3 (X) is (are)
(A) The total number of stereoisomers possible for X is 6
(B) The total number of diastereomers possible for X is 3
(C) If the stereochemistry about the double bond in X is trans, the number of enantiomers possible for X
is 4
(D) If the stereochemistry about the double bond in X is cis, the number of enantiomers possible for X
is 2 [JEE 2009]
Q.24 The total number of cyclic isomers possible for a hydrocarbon with the molecular formula C4H6 is
[JEE 2010]
Q.25 In the Newman projection for 2,2-dimethylbutane [JEE 2010]

X
H3C CH3
H H
Y
X and Y can respectively be
(A) H and H (B) H and C2H5 (C) C2H5 and H (D) CH3 and CH3
Q.26 The maximum number of isomers (including stereoisomers) that are possible on mono-chlorination of the
following compound, is [JEE 2011]
Q.27 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]
(A) (B) H – C 
(C) H2C = C = O (D) H2C = C = CH2

Q.28 Which of the given statement(s) about N, O, P and Q with respect to M is (are) correct? [JEE 2012]
Cl
HO H HO H CH3 CH3
H H OH HO H
OH
Cl CH3
HO H H OH HO H
HO H HO H
CH3 Cl CH 3 Cl Cl
(M) (N) (O) (P) (Q)
(A) M & N are non-mirror image stereoisomers (B) M & O are identical
(C) M & P are enantiomers (D) M & Q are identical
Q.29 The total number(s) of stable conformers with non-zero dipole moment for the following compound is
(are) [JEEAdvance 2014]
Cl
Br CH3
Br Cl
CH3
Q.30 The total number of stereoisomers that can exist for M is : [JEEAdvance 2015]
H3C CH3
H3C O
M
Q.31 For the given compound X, the total number of optically active stereoisomers is ____.
[JEEAdvance 2018]
HO HO This type of bond indicates that the configuration at the
specific carbon and the geometry of the double bond is fixed
This type of bond indicates that the configuration at the

HO HO specific carbon and the geometry of the double bond is NOT fixed
X
EXERCISE-4
(Potential Problems Based on CBSE)

Very Short Answer Type Questions
Q.1 Why eclipsed and staggered forms of ethane cannot be isolated at room temperature?
Q.2 What is the cause of geometrical isomerism?
Q.3 What are conformations?
Q.4 Which of the following exhibits geometrical isomerism?
(a) 2-methyl propene (b) 1-butene
(c) 2-butene (d) 2,3-dibromo-2-butene
Q.5 Draw the Newman’s projection formula of the staggered form of 1, 2-dichloroethane.
Q.6 How many possible conformations of ethane are there?
Q.7 What is difference between conformation and isomers?
Q.8 Name the structures obtained by free rotation along the C–C bond.
Q.9 Is geometrical isomerism possible around triple bond?
Short Answer Type Questions

Q.10 Identify the type of isomerism exhibited bythe following compounds:
(i) CH3– CH = CH – CH3 (ii) CH3 – CH = CH – CH2 – CH3
(iii) CH3 – CH2 – CH2 – CH3 (iv) C5H12
Q.11 Draw structures to illustrate.

(i) Geometrical isomerism
(ii) Positional isomerism
Q.12 Classify the following as cis-isomer or trans-isomer or having no geometrical isomers:

H CH3 CH3–CH2 C2H5
(a) C=C (b)
C=C
H CH3 H H
Cl Cl CH3CH2 CH3
(c) C=C (d) C=C
H H CH3 CH2CH3
Long Answer Type Questions

Q.13 Draw main conformations of n-butane obtained by rotation around C–2 and C–3.Also give the names
of these conformations. Which of these conformations is most stable and which is the least stable and
why?
EXERCISE-5 (Rank Booster)
[SINGLE CORRECT CHOICE TYPE]
Q.1 Which of the following structure can show geometrical isomerism?

NO 2 NO 2
(A) (B) 2,3-Dimethyl but-2-ene

HOOC
COOH
(C) 3,4-Diethyl hex-2-ene (D) 1,4-Dichloro benzene
Q.2 What is the correct IUPAC name of the following compound
(A) 2E, 4E, 6Z 4-methyl oct-2, 4, 6 triene (B) 2E, 4Z, 6Z 5-methyl oct-2, 4, 6 triene
(C) 2Z, 4Z, 6Z 5-methyl oct-2, 4, 6 triene (D) 2E, 4Z, 6E 4-methyl oct-2, 4, 6 triene
Q.3 Molecular formula C5H10O can have :

(A) 6-Aldehyde, 4-Ketone (B) 5-Aldehyde, 3-Ketone
(C) 4-Aldehyde, 3-Ketone (D) 5-Aldehyde, 2-Ketone
Q.4 The number of isomers of dibromoderivative of an alkene (molar mass 186 g mol–1) is
(A) 2 (B) 3 (C) 4 (D) 6
Q.5 On chlorination of propane number of products of the formula C3H6Cl2 is

(A) 3 (B) 4 (C) 5 (D) 6
Q.6 The correct stability order of the following species is
H H Me
H Me
Me
Me H Me
(a) Me
H H
(b) (c)
(A) c < a < b (B) c = b < a (C) c < a = b (D) a = b = c
Q.7 Identify diastereoisomer in the following are :
H CH3 Cl
CH3
Cl CH3 H Cl
H Cl CH3 H
(A) (B) CH3 H CH3 H
Cl CH3 H Cl
Cl Cl
H CH3
CH3 CH3
H CH3
Cl CH3 Cl
H Cl H Cl H
(C) H Cl Cl H (D) H Cl
H Cl CH3
CH3 CH3
CH3
Q.8 What is relationship between ?
HOOC Br H COOH
H Br
H COOH
H Br COOH Br
(A) Enantiomer (B) Diastereomer (C) Conformer (D) Identical
Q.9 The structure of (2R, 3R)C2H5CH(CH3)CH(D)CH2D is
(A) (B) (C) (D)
Q.10 The structure of (2R, 3S)C2H5CH(CH3)CH(D)CH2D is
(A) (B) (C) (D)
Q.11 Select the correct IUPAC name of following compound :

NH2
H COOH
H CONH2
COOH
(A) 2R,3S-3- amino-2- carbamoyl butane-1,4-dioic acid
(B) 2S,3R-2-amino-3- carbamoyl butane-1,4-dioic acid
(C) 2S, 3R-3-amino-2-carbamoyl butane-1-4-dioic acid
(D) 2R, 3R-2-amino-3- carbamoyl butane-1-4-dioic acid
[ONE OR MORE THAN ONE CORRECT CHOICE TYPE]

Q.12 Total number of geometrical isomer of following compound.
(A) 2 (B) 4 (C) 8 (D) 16
Q.13 In which of the following has minimum torsional strain and minimum Vander waal strain.
CH3 CH3
CH3 CH3 CH3
H H H CH3
CH3
CH3 H H H
H CH3 CH3 H CH3
CH3 CH3
CH3 CH3 CH3
I II III IV
(A) I (B) II (C) III (D) IV
Q.14 Which of the following statements for a meso compound is correct?

(A) The meso compound has either a plane or a centre of symmetry
(B) The meso compound is chiral.
(C) The meso compound is achiral
(D) The meso compound is formed when equal amounts of two enantiomers are mixed.
Q.15 Which of the following pairs can be resolved?
(A) (B)
HOOC COOH HOOC COOH
(C) (D)
NO2 NO2 NO2 NO2
Q.16 Which of the following is not of pair of enantiomers?

Cl Cl H Br Br H
Cl Cl C=C=C C=C=C
(A) (B)
Br H H Br
H CH H CH3 CH3
3 H Cl Br H
C C
(C) H 3C (D) H Br Cl H
Br
Br CH3 CH3
Q.17 Which of the following molecules is/are identical with that represented by
(A) (B) (C) (D)
Q.18 Which of the following is/are the correct Fischer projection of the following :
CH3 C2H5 Et
CH3
H OH HO H H OH H OH
(A) H OH (B) HO H (C) HO H (D) H OH
H OH HO H H OH HO H
C2H5 CH3 C2H5 CH3
[REASONING TYPE]
Q.19 Statement-1 : E-cyclopentadecene is having more HC (Heat of combustion) than
Z isomer.
Statement-2 : E-cyclopentadecene is more stable than Z isomer.
(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 the correct explanation for statement-1.
(C) Statement-1 is true, statement-2 is false.
(D) Statement-1 is false, statement-2 is true.
[MATCH THE COLUMN]
Q.20 Match the column :
Column-I Column-II
CH3 H
H CH2OH H3C CH2NH2
(A) and (P) Structural isomer
NH2 OH
CH3 Cl
H Cl H CH3
(B) and (Q) Identical
Et Et
CH3 H
H H3C Et
OH
(C) and (R) Enantiomers
Et OH
H5C2 H5C2
(D) and (S) Diastereomers
OH H H OH
Q.21 Match the Column :

Column I Column II
COOH COOH
H OH H OH
;
(a) A pair of metamer (i) HO H H OH
COOH COOH
(b) tautomerism (ii) CH3OC3H7 ; C2H5OC2H5
CH3 CH3
H OH ; HO H
(c) A pair of geometrical isomer (iii)
COOH COOH
CH3 CH3 H3 C H
(d) A pair of distereomers (iv) C=C ; C=C
H H H CH3
O
||
(e) A pair of optical isomer (v) CH 3CH 2CH 2CH ; CH3CH2CH=CH–OH
[SUBJECTIVE]
Q.22 Assign E & Z configuration?
O O
O
O
(I) (II)
O
Z E
CH2CH2CH3
Ph
(III) CH – CH3 (IV) Cl
|
CH3
F
| NC CH = CH2
C–C–C Br
(V) F (VI)
HOOC CHO
C–C–C Cl
Z
C  CH O
HO
CH3 O O
(VII) OHC C – CH3

|
(VIII) O
O
CH3 O
18
Me OMe OH
H
(IX) (X) 16
Et O¯ Li
+
D OH
CH3
|
CH – CH2 – CH3
Me F
C  CH
(XI) (XII)
Cl Me CH3
H
Q.23 Determine whether each of the following compounds is a cis isomer or a trans isomer.
(a) (b)
(c) (d)
(e) (f)
Q.24 Calculate the number of chiral center in the molecule Ethyl 2,2-dibromo-4-ethyl-6-methoxycyclohexane
carboxylate.
Q.25 With reasons, state whether each of the following compounds I to VII is chiral.
(I) (II) (III)

HO2C CO2H
(IV) (V) (VI) (VII) S

O Ph
Me
Q.26 What are the relationships between the following pairs of isomers?
Cl Cl
(a) and (b) and
Cl Cl
(c) and
(d) and
(e) and (f) and
(g) and (h) and
(i) and
Q.27 Total number of streoisomers for the following molecule : (including optical)
(i) CH3 – CH – CH = CH CH = CH – CH – CH3 (ii)

| | Me
Cl CH3 COOH
NH2
N O
O N
(iii) EtO – P N N (iv)

OH
OEt
OH
(v) (vi)
O
ANSWER KEY
EXERCISE-1
Q.1 4 Q.2 6
H H Et
Q.3 (a) (b)

H H
H H H
Et H
Q.4 (a) 4,1,2,3 (b) 4,1,2,3 (c) 1,3,2,4 (d) 4,3,2,1 (e) 2,4,3,1 (f) 4,2,3,1 (g) 3,1,4,2 (h) 2,4,1,3
(i) 3,2,1,4 (j) 2, 1, 4, 3
Q.5 (i) (ii)

Me
Pr
C2H5
H Br
(iii) (iv)
CH3
C3H7 CH3
H Br
Br Cl
(v) (vi) H Br
C2H5 CH3
Q.6 (i) Z, (ii) Z, (iii) Z, (iv) E
Q.7 Stable are : (a) diequatorial, (b) , (c) (d) ,
(e) , (f)
Q.8 (i) Trans (ii) Cis (iii)Trans (iv) Cis
Q.9
Q.10 8 Q.11 4 Q.12 (i) 6, (ii) 8, (iii) 6, (iv) 6
Q.13 Optical : a,b,c,d,f,g,i,j,k ; Geometrical isomer : c,g,j ; None : e,h,
Q.14 3,1 Q.15 (I) 4, (II) 3, (III) 4 Q.16 4
Q.17 (i) 24 (ii) 4 Q.18 9
Q.19 II, III & IV are Identical; I is Enantiomer of these. Q.20 0630
EXERCISE-2
Q.1 B Q.2 C Q.3 C Q.4 A Q.5 C Q.6 D Q.7 A
Q.8 A Q.9 B Q.10 D Q.11 A Q.12 B Q.13 C Q.14 C
Q.15 B Q.16 D Q.17 B Q.18 B Q.19 C Q.20 B Q.21 A
Q.22 D Q.23 D Q.24 C Q.25 A Q.26 C Q.27 D Q.28 C
Q.29 B Q.30 A Q.31 B Q.32 C Q.33 D Q.34 C Q.35 C
Q.36 D Q.37 A Q.38 A Q.39 A Q.40 BCD Q.41 BC Q.42 D
Q.43 ABD Q.44 BC Q.45 BC Q.46 ABC Q.47 AC Q.48 AC Q.49 C
Q.50 AD Q.51 ACD Q.52 AC Q.53 CD Q.54 ACD Q.55 AC Q.56 AD
Q.57 BC Q.58 C Q.59 A Q.60 AC Q.61 B Q.62 AD Q.63 ACD
Q.64 ACD Q.65 (A) P,R,S ;(B) Q; (C) Q,R; (D) P,R,S
Q.66 (A) Q (B) Q (C) S (D) P Q.67 (A) P, (B) S, (C) R, (D) Q
Q.68 (a-4-iii) ; (b-3-iv) ; (c-2-ii) ; (d-1-i) Q.69 (A) R , (B) P, (C) Q
EXERCISE-3
SECTION-A
Q.1 C Q.2 B Q.3 D Q.4 A Q.5 D Q.6 A Q.7 B
Q.8 A Q.9 B Q.10 A Q.11 A Q.12 A Q.13 A Q.14 C
Q.15 A Q.16 C Q.17 C Q.18 C

SECTION-B
Q.1 True Q.2 A Q.3 C Q.4 BC Q.5 B Q.6 B Q.7 A
Q.8 D Q.9 AC Q.10 enantiomers–I & III; diastereomers – I & II and II & III
Q.11 A Q.12 D Q.13 D Q.14 B Q.15 C Q.16 B
1
Q.17 (i) D, (ii) Anti form when Y=CH3 & Gauche when Y = – OH Q.18 C
0.18
Q.19 C Q.20 AD Q.21 BCD Q.22 7 Q.23 AD Q.24 5 Q.25 BD
Q.26 8 Q.27 BC Q.28 ABC Q.29 3 Q.30 2 Q.31 7
EXERCISE-5
Q.1 C Q.2 D Q.3 B Q.4 B Q.5 C Q.6 C Q.7 D
Q.8 B Q.9 A Q.10 B Q.11 B Q.12 B Q.13 B Q.14 AC
Q.15 BCD Q.16 ABCD Q.17 AD Q.18 AB Q.19 D
Q.20 (A) P , (B) R , (C) Q , (D) R Q.21 (a) ii (b) v (c) iv (d) i, iv (e) i, iii
Q.22 Z – I, II, III, VI, VII ; E – IV, V, VIII, IX, X, XI, XII
Q.23 (a) cis (b) cis (c) cis (d) trans
(e) trans (f) trans
Q.24 3
Q.25 achiral : I, III, IV ; chiral : II,V, VI, VII
Q.26 (a) Enantiomers, (b) Identical, (c) Geometrical isomers & Diastereomers, (d) Positional,
(e) Optical (Diastereomers), (f) Diastereomers, (g) Enantiomers, (h) Identical, (i) Geometrical isomers
(Diastereomers)
Q.27 (i) 25 , (ii) 24 , (iii) 2 , (iv) 4 , (v) 3, (vi) 8
sgnsdfjngsrgnjn

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JEE (MAIN+ADVANCED)

Structural Isomerism Stereoisomerism

STEREOISOMERISM / SPACE ISOMERISM

Not showing G.I. Showing G.I.

Geometrical isomers are named as

HOOC COOH HOOC H

Priority rule : cahn, ingold & prelog proposed a sequence rule.

(2) CH3 CH3

Geometrical Isomerism in Azo compound :

Geometrical Isomerism in cyclo alkane :

No. of geometrical isomers in polyenes :

Ex.- CH 3 – CH = CH – CH = CH – CH2 – CH3

Configurational isomers which are differ in their optical activity.

Following experiment was conducted to determine the optical activity of a substance

Cause of optical activity:-

A chiral molecule or object is non-superimposable on its mirror images.

(a) Perspective formulae :

C2H5 C2H5 COOH COOH

Enantiomers of 2-butanol Enantiomers of lactic acid

Important Points About Fischer Projection Formula :

COOH COOH COOH COOH

CH3 CH3 CH3 CH3

Characteristics of Diastereomers are :

(iv) Diastereomers are also encountered in the case of geometrical isomers :

(1) Relative method of configuration (D, L System) :

(i) (ii) (iii)

D-form D-form L-form

R–S system (Absolute configuration)

Movement of eyes in anticlockwise = S

Optical Isomerism in compound containing no chiral carbon atom

(ii) Alkylidene, cycloalkanes and spiro compounds :

H3C H a CH2 CH2 a

NO2 HOOC COOH F

Number of optical isomers :

Number of meso form = 2(n/2 – ½)

Projection of Tetrahedral Carbon Atom :

H C-H bond of front carbon

Dihedral angle :– Angle between valencies of two adjacent atoms

0 60° 120° 180°

Eclipsed Staggered Eclipsed

Eec – Est = 13.8 kJ/mole

Exercise : (i) n-pentane (about C2–C3)

Some important example :

(ii) n-hexane (C2–C3) rotation

due to intraction between flag pole hydrogens boat conformation is unstable.

Conformation of mono substituted cyclohexane :

Write the orders of equilibrium constant for following equilibrium.

Draw most stable chair conformation of following compound.

EXERCISE-1 (Subjective Questions)

Q.2 How many geometrical isomers are possible by

Q.3 Considering rotation about the C-3 – C-4 bond of 2-methylhexane:

Q.5 Write the structure of :

Q.6 Write the E / Z configuration of each compound.

Q.8 Write the configuration of each compound?

Q.9 Draw the most stable conformer of N-methylpiperidine.

Q.11 How many enantiomers are possible on monochlorination of isopentane.

Q.12 Calculate the total number of chiral carbon atoms in.

(e) (f) Et(Me)C=C=C(Me)Et

Q.15 Calculate the total number of stereoisomers in the following compounds.