Geometrical Isomerism (Animated)

AvisualStudy
in
S.
K
.S
in
ha
GEOMETRICALISOMERISM
By
S.K.Sinha
ResonanceKota
Checkouttheunique3Dvisualpresentationforthe1st timeat
https://play.google.com/store/apps/details?id=air.geo.isomer
STEREOISOMERISM
Isomers with different orientation
or distribution of atoms or group
of atoms in space are called
stereoisomers.
2.
Stereo-isomers
.S
in
ha
1.
have identical
connectivity of atoms and groups
S.
K
( bond pattern).
pattern)
Checkout the unique 3D visual presentation for the 1st time at

STEREOISOMERISM
Example:
p
cis and trans 2butene has identical bond
pattern.
S.
K
.S
in
ha
1.

STEREOISOMERISM
Geometrical Isomerism
is a
form of configurational stereo
isomers.
2.
Any
two
configurational
isomers are stereoisomers, but
can not be interconverted
S.
K
.S
in
ha
1.

STEREOISOMERISM
These isomers differ in the
configuration
(The
spatial
arrangement) or Arrangement
of atoms in space.
p
S.
K
.S
in
ha
1.

CONFIGURATIONALISOMERISM
Configurational
g
isomerism
arises
due
to
noninterconvertibility of bonds at
room temperature.
p
S.
K
.S
in
ha
1.

CONFIGURATIONALISOMERISM
They
y are non interconvertible ,
they can be separated by
physical
and
chemical
methods.
S.
K
.S
in
ha
1.

Isomers
with
different
geometrical arrangement of
group of atoms or atoms in
space
are
known
as
geometrical isomers
S.
K
.S
in
ha
1.

1.
Example
O
C
C
C
in
OH
ha
.S
OH
Fumaric Acid
S.
K
OH O
OH
C
H
Maleic Acid

Example
S.
K
.S
in
ha
2.

Conditions for G.I.
S.
K
.S
in
ha
Cis-trans isomerism

Conditions For GI :
For GI to occur, presence of a
functional group or condition
of restricted rotation is
required . It is represented by
GRR (i.e. -C=C- , -C=N- , -N=Nor ring str.)
str )
S.
K
.S
in
ha
1.
2.
GRR = Group with restricted

rotation

Conditions
Co
d t o s for
o G.I
G :
in
ha
2. Non-convertability
.S
S.
K
b
a
X
b

Conditions for G.I :
Different groups should be
attached
at
each
doubly
bonded atom (or on the sides
of GRR GROUP)
S.
K
.S
in
ha
3.

and
b
in
.S
are identical but not G.I.
ha
S.
K
and
can show G.I.

Conditions for G.I :
S.
K
.S
in
1. example
ha
4. Different groups should be in

one plane (Planarity)

following types of compound
can show geometrical isomers
:
S.
K
.S
in
ha
1
1.

S.
K
.S
in
ha
A. Compounds
p
with C=C(Alkene
(
)

S.
K
.S
in
ha
trans-2-Butene has lesser

dipole moment than cis -2butene.

Cis has high
g B.P. than trans.
S.
K
.S
in
ha
But trans has high mp than cis.

A Compounds
p
with C=C
OH
OH
O
Fumaric Acid
O C
C
S.
K
.S
OH
in
ha
C
H
C
H
Maleic Acid

OH
Maleic acid form Anhydride
y
C
C
OH
.S
Maleic Acid
in
ha
OH O
Maleicanhydride
y
S.
K
Fumaric acid: No Anhydride
OH
No anhydride
OH
Fumaric Acid
.S
in
ha
cis and trans 1,2-Dichloroethene

,
S.
K
g/
Z:1.28g/cm
o g
Boiling
Density
E:1.26g/cm point
Melting Z:81C
point
E: 81 C
E:81
C
60 3 C
Z:60.3C
E:47.5C
Z(cis):1.9
Dipole D
E (trans):
(t
) 0
0
momentt E
D

S.
K
.S
in
ha
cis and trans Stilbene

S.
K
.S
in
ha
cis and trans Stilbene

cis-Stilbene has a melting
gp
point
of 5-6 C, while trans-stilbene
melts around 125 C
CH
HC
ha
CH
CH
CH
in
CH
S.
K
.S
HC
CH CH
HC
CH
CH
HC
CH
HC
CH
CH
CH C
C
C
CH
CH
C
H

B. Compound
p
with C=N bond
S.
K
.S
in
ha
(imine, oxime )

Compounds
p
with C=N: Hydrazones
y
ha
NH2
.S
H 3C
in
E-Acetaldehydehydrazone
S.
K
H 2N
H 3C
N
C
H
Z-Acetaldehydehydrazone
CH CH
C
NH
in
HC
ha
Compounds
p
with C=N: Phenyl
y
hydrazones.
.S
CH CH
C
Ph
S.
K
E-Benzaldehydephenylhydrazone
CH CH
HC
CH CH
H
N
NH
C
Ph
Z-Benzaldehydephenylhydrazone
Compounds
p
with C=N:
Semicarbazone
ha
H 3C
S.
K
.S
in
NH
O
C
NH2
NH
NH2
H 3C
S.
K
.S
in
ha
C. Compounds
p
with N=N ((Azo))

Compounds
p
with N=N :
Azobenzene
CH CH
ha
CH CH
CHHC
in
HC
CH
.S
CH C
CH
S.
K
CH
HC
CH
CH
C
CH
N
N
CH
C
CH
CH
CH
CH

S.
K
.S
in
ha
D. Compounds
p
with Cycles
y

S.
K
.S
in
ha
D Compounds with Cycles

S.
K
.S
in
ha
D. Compounds
p
with Cycles
y

S.
K
.S
in
ha
D Compounds
p
with Cycles
y

S.
K
.S
in
ha
E. Cyclooctene or higher alkene

S.
K
.S
in
ha
F. Cumulene with odd no

S.
K
.S
in
ha
G. Spirane
p
with odd rings
g

spirane
p
with odd no of rings
g
S.
K
.S
in
ha
trans Spirane
transSpirane

H. spiroallene
p
with odd no of
S.
K
.S
in
ha
( + rings)

S.
K
.S
in
ha
I. Decaline

S.
K
.S
in
ha
CONCEPT TESTING
CONCEPTTESTING

S.
K
.S
in
ha
1 Is G I possible in given compound ?

1.IsG.I.possibleingivencompound?

S.
K
.S
in
ha


S.
K
.S
in
ha


S.
K
.S
in
ha


S.
K
.S
in
ha


ha
A. 1,2-dichloropropene
S.
K
.S
in
B. 2,3- dichloro -1-butene

A. 1,1-dichlorocyclopropane
B 1,2
B.
1 2 dichlorocyclopropane
S.
K
.S
in
ha
C. 1,3-dichlorocyclohexene

Yes
2
2.
No
3.
No
4.
Yes
5.
No
6.
A Yes
7.
B No
B Yes
C No
S.
K
.S
No
in
1.
ha
Solution

Formation of Oxime.
S.
K
.S
in
ha
Symmetrical aldehyde /ketone

form one oxime.
CH2 CH2
H2C
C O
CH2 CH2
N OH
sym ald/ketone
CH2 CH2
C N
H2C
CH CH2
OH
only one oxime

Formation of Oxime
form one oxime.
CH CH
C
CH2 CH2
OH
S.
K
CH2 CH2
.S
H2C
in
ha
Unsymmetrical aldehyde
/ketone form two oxime.
H2C
CH CH
H2C
CH CH
unsym
y ald/ketone
CH2 CH2
OH
CH2 C
C
CH2
OH
H2C
OH
N
CH CH
form two oxime

Formation of Oxime
H3C
H3C
CH2
C
H3C
H3C
OH
S.
K
CH2
.S
C
H3C
in
ha
/ketone form two oxime.
unsym ald/ketone
OH
C
H3C
H3C
CH2
CH2
OH
OH
N
H3C
form two oxime

Formation of Hydrazone
H
N NH2
C O
H
.S
H3C
H3C
in
C O
unsym ald/ketone
NH2
C N
H3C
H3C
N NH2
S.
K
H
ha
/ketone form two
Hydrazones.
NH2
C N
H
form two hydra

Formation of Hydrazone
.S
N NH2
C O
S.
K
in
ha

form one Hydrazone.
sym ald/ketone
NH2
C N
form one hydra

Formation of Oxime
.S
in
ha

form one oxime.
H3C
N OH
S.
K
H3C
H3C
sym ald/ketone
OH
C
H3C
form one oxim

Nomenclature in G I
NomenclatureinG.I
Cis / trans: similarity of groups
S.
K
.S
in
ha
1 Similar groups on the same

1.
side or nearest : cis
2. Similar groups on the opposite

side or farthest : trans

S.
K
.S
in
ha
CONCEPTTESTING

S.
K
.S
in
ha
Q1
Are these two cis trans
isomers?

Are these two cis trans isomers
S.
K
.S
in
ha
Q2
?

S.
K
.S
in
ha
Q3
?

S.
K
.S
in
ha
Q4
?

S.
K
.S
in
ha
Q5
?

S.
K
.S
in
ha
Q6
?

S.
K
.S
in
ha
Q7
?

Q8 Relation between the given pair
of compound is ..
ha
Cl
H C
H
C H
Cl C
H
S.
K
.S
in
CH2H
Cl
Cl C
H
C H
H C
H
C
H
C H
H
C H 2H
H
C
H
C
H

of compound is ..
S.
K
Cl
H C
H
C H
Cl C
H
C H 2H
ha
.S
in
H
C
H
Cl
C
Cl
H
C
H
H
C
H
CH2H
C
H
C H
H

C
H
CH2
in
H 3C
ha

of compound is ..
.S
S.
K
H 3C
Cl
CH2
H 3C
H 3C
CH2
CH3
CH2
CH3
Cl
of compound is ..
CH
CH
CH2
ha
CH2
CH2
CH2
CH3
CH
CH
S.
K
H 3C
.S
in
H 3C
CH2
CH2
CH2
CH2
CH3

of compound is ..
ha
CH
in
CH
CH
CH
CH2
CH2
CH3
CH3
CH2
S.
K
H 3C
CH2
CH2
.S
H 3C

of compound is ..
ha
in
CH2 C
CH2
.S
H 2C
S.
K
CH3
H 3C
CH 2
CH3
H
C
CH 2
CH 2
CH 3
H
of compound is ..
CH2
C
CH3
S.
K
.S
in
H 3C
CH2
O
ha
H 3C
CH2 C
CH2
C
H 3C

of compound is ..
CH
HC
C
in
H 2C
CH2
ha
H 2C
.S
S.
K
H
H
H 2C
CH
C
C
CH2
CH2
CH
H
of compound is ..
Cl
ha
Br
CH2
.S
H 2C
in
S.
K
Cl
Cl
C
H 2C
Cl
H
CH2
H
C
Br

of compound is ..
ha
CH3
HC
H 2C
H 2C
CH
CH2
CH2
.S
CH2
S.
K
H 2C
CH2
in
H 2C
CH
CH 2
CH 2
CH2
CH 2
CH
CH 2
CH
CH
CH 3
CH 2

.S
in
No
No
No
No
Yes
No
No
Geometrical
Positional
Geometrical
Positional
Homologous
Identical
Geometrical
Geometrical
Geometrical
Geometrical
S.
K
1.
2.
3.
4.
5.
6.
7.
8.
8.
10
10.
11.
12.
13
13.
14.
15.
16
16.
17.
ha
Answer

Nomenclature in G I
NomenclatureinG.I
Cis / trans: similarity of groups
S.
K
.S
in
ha
1 Similar groups on the same

1.
side or nearest : cis
2. Similar groups on the opposite

side or farthest : trans

Nomenclature in G I
NomenclatureinG.I
E and Z : Based on seniority
ha
Seniors /high priority groups on the

same side or nearest : Z
.S
in
(Z = zusammen = together)
S.
K
Seniors /high priority groups on the

opposite side or farthest :E
(E
= entgegen = opposite)

Sequence rules : (CIP rules)

Sequencerules:(CIPrules)
Rules for seniority
.S
in
ha
Rule I : Greatertheatomic
numberof1st atom,greater
theseniorgroup.
S.
K
I>Br>Cl >S>F>O>N>C


S.
K
.S
in
ha
Rule II : Ifatomicnumberis
samethenisotopeswiththe
greatermassnohasgreater
priority.
Ex.(a) T> D> H
(b)C14H3 > C12H3


S.
K
.S
in
ha
Rule III :Ifthefirstatomis

identicalthansecondatomis
observedforseniority.
Ex.(a) CH2Cl> CH2OH>
CH2NH2>CH2CH3 > CH3


S.
K
.S
in
ha
Rule IV : Groupscontaining
doubleortriplebondsare
assignedseniorityasifthe
bondsareconnectedwith
separateatoms..
t t


.S
CH CH2
S.
K
H 3C
H 3C
in
ha
Ex.fordecidingseniorityamong C
Cand CH =CH2 ,their
h pothetical eq i alents are
hypotheticalequivalentsare
compared.
CH
H 3C
CH3
C
CH3
H
H 3C
CH3
C
CH3
CH3


ha
Rule V :Bondpairisseniortolone
pair.
S.
K
.S
in
Greater Priority
GreaterPriority
H
N

S.
K
.S
in
ha
CONCEPTTESTING

ha
Q1
Check , if the given compound is
Z or E.
CH3
.S
S.
K
in
Cl
B
Br
CH2 CH3

ha
Q2: Check , if the given compound is

Q2
Z or E.
HC
.S
H 2N
in
OH
S.
K
Br
CH 3
CH 2 CH 3

in
ha

Q3
Z or E.
HO
.S
S.
K
CH2
Br
CH2
CH3
C
CH2

ha

Q4
Z or E.
in
H 3C
HO
C
CH2
S.
K
Br
.S
CH2
CH2
CH CH3
C
CH3

in
ha

Q5
Z or E.
S.
K
H 3C
.S
CH 3
C
H

ha

Q6
Z or E.
CH
H 3C
.S
CH 2
S.
K
Cl
in
CH 2
CH
CH
CH
CH
HC
CH
CH
CH

CH
ha

Q7
Z or E.
OH
S.
K
.S
in
H 3C

Q8
Z or E.
ha
CH CH
OH
in
HC
CH
CH
S.
K
.S
Cl
H 2C
I HC
CH
CH CH

Q9
Z or E.
in
H3C
ha
H3C
CH2
S.
K
H3C
.S
CH2
C
CH

H3C
ha

Q10
Z or E.
H3C
CH
.S
H3C
S.
K
CH2 CH2
H2C
in
CH
CH2
C
CH

in
.S
Z
E
E
E
E
Z
Z
Z
Z
E
S.
K
1.
2.
3.
4
4.
5.
6.
7.
8.
8
8.
10.
ha
Answer

Number of G I:
S.
K
.S
in
ha
Numbers of geometrical
isomers can be found by
g the number of
calculating
stereocenters in the
compound.

Number of G I:
CH
CH
CH
CH
S.
K
H 3C
.S
in
ha
Step-1: Count total no.

no of
possible stereocenter
where GI is possible.
G.I possible
CH
CH
CH
CH2
CH2
G.I not possible

Number of G I:
.S
in
ha
Step-2: See if both ends are

identical or not.
S.
K
If both ends are not identical

then total no of possible
GI = 2n ,
where n= no of stereocenters.

Number of G I:
.S
in
ha
Step-2: See if both ends are

identical or not.
S.
K

GI = 2n ,
where n= no of stereocenters.

CH
CH
CH
C
CH
S.
K
H 3C
.S
in
ha

GI = 2n , where n= no of
stereocenters.
stereocenters
G.I possible
CH
CH
CH
CH 2
CH 2
G.I not possible
Heren=3
TotalnoofGI=23 =8
S.
K
.S
in
ha
Step-i: if both ends are

identical .Then see if the
no of possible
stereocenters are odd/
even.
ii. If n = no of stereocenter
is even then total no of GI
= 2(n-1)+2 ((n/2)-1)
H 3C
CH
CH
CH
CH
CH
CH
CH
CH
CH3
G.I possible
Heren=4
TotalnoofGI=10
S.
K
.S
in
ha
Step-i: if both ends are

identical .Then see if the
no of possible
stereocenters are odd/
even.
ii. If n = no of stereocenter
is odd then total no of GI
= 2(n-1)+2 ((n-1)/2)
H3C
CH
CH2
CH
CH
CH
CH
CH2
CH3
CH
G I possible
G.I
ibl
Heren=3TotalnoofGI=6
S.
K
.S
in
ha
CONCEPTTESTING

H 2C
HC
.S
CH
CH
CH
CH 3
in
CH
ha
Q:1 Find total no of

geometrical isomer for
CH
CH
S.
K
CH 2

H 2C
CH
CH2
.S
H 2C
in
ha

S.
K
CH2
CH
CH
CH
Cl
CH2
CH2

ha

H3C
in
CH
CH
H3C
S.
K
H3C
CH
.S
H2C
CH3
CH2
CH2

ha

CH3
H 3C
in
CH
H 3C
S.
K
H 3C
.S
CH
CH2
C
CH3
CH3
NH

CH C
CH CH CH CH3
S.
K
H2C
.S
H3C
in
ha


Q:6 How many products are
formed in given reaction
ha
C
H 3C
in
CH3
H 2N
OH
.S
Q7H
Q:7
How many products
d t are formed
f
d
in given reaction
S.
K
H 2C
CH2
H 2C
CH2
CH2
H 2N
OH

Q:8 How many products are formed in
given reaction
ha
O
C
C
NH2
.S
H 2C
H 2N
in
CH2
H 2C
CH2
S.
K
Q:9 How many products are formed in

given reaction
CH 2
O
+ H 3C
C
H 3C
CH 3
H 2N
OH
CH 3

10. How many products are formed in
given reaction
C
CH2
H 2N
OH
ha
O
+
in
H 2C
CH2
.S
S.
K
11. How many products are formed in

given reaction
H2C
CH2
C
O
H2N OH
CH2
CH2
ha
12 Write all Isomers of C4H8

12.WriteallIsomersofC
13.WriteallIsomersofC5H10
in
14.WriteallGIofC2HClBr2
.S
15 Write all GI of C2HClBrI

15.WriteallGIofC
HClBrI
S.
K
16.WriteG.Iof1,3,5,7Octatetraene


Geometrical Isomerism (Animated)

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AvisualStudy

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GRR = Group with restricted

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are identical but not G.I.

can show G.I.

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4. Different groups should be in

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trans-2-Butene has lesser

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But trans has high mp than cis.

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Fumaric acid: No Anhydride

cis and trans 1,2-Dichloroethene

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cis and trans Stilbene

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cis and trans Stilbene

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D Compounds with Cycles

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E. Cyclooctene or higher alkene

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F. Cumulene with odd no

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1 Is G I possible in given compound ?

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2 Is G I possible in given compound ?

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3 Is G I possible in given compound ?

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4 Is G I possible in given compound ?

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5 Is G I possible in given compound ?

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B. 2,3- dichloro -1-butene