Geometrical Isomerism By S.K.Sinha
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Transcript of Geometrical Isomerism By S.K.Sinha
A visual Studyin
GEOMETRICAL ISOMERISM
By
S.K.SinhaResonance Kota
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S.K.S
inha
STEREOISOMERISM1. Isomers with different orientation
or distribution of atoms or groupof atoms in space are calledstereoisomers.
2. Stereo-isomers have identicalconnectivity of atoms and groups( bond pattern)( bond pattern).
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1. Example: cis and trans 2-
STEREOISOMERISM
pbutene has identical bondpattern.
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1. Geometrical Isomerism is a
STEREOISOMERISM
form of configurational stereoisomers.
2. Any two configurationalisomers are stereoisomers, butcan not be interconvertedcan not be interconverted
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1. These isomers differ in the
STEREOISOMERISM
configuration (The spatialarrangement) or Arrangementof atoms in space.p
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1. Configurational isomerism
CONFIGURATIONAL ISOMERISM
garises due to non-interconvertibility of bonds atroom temperature.p
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inha
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1. They are non interconvertible ,
CONFIGURATIONAL ISOMERISM
y ,they can be separated byphysical and chemicalmethods.
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1. Isomers with different
GEOMETRICAL ISOMERISM
1. Isomers with differentgeometrical arrangement ofgroup of atoms or atoms inspace are known asspace are known asgeometrical isomers
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1. Example
GEOMETRICAL ISOMERISM
1. Example
O
C C
C O HH
HCO
O H
OO H
O HFumaric Acid
C O HCO
C C
HH HH
Maleic Acid
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GEOMETRICAL ISOMERISM
2. Example2. Example
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Conditions for G.I.
GEOMETRICAL ISOMERISM
Conditions for G.I.
Cis-trans isomerism
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Conditions For GI :
GEOMETRICAL ISOMERISM
1. For GI to occur, presence of a functional group or condition of restricted rotation isof restricted rotation is required . It is represented by GRR (i.e. -C=C- , -C=N- , -N=N-or ring str )or ring str.)
2. GRR = Group with restricted rotationS.K
.Sinh
a
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Conditions for G.I :
GEOMETRICAL ISOMERISM
Co d t o s o G2. Non-convertability
aa ba
Xbb ab
X
a ba a
Xb ab b
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Conditions for G.I :
GEOMETRICAL ISOMERISM
3. Different groups should beattached at each doublybonded atom (or on the sidesbonded atom (or on the sidesof GRR GROUP)
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GEOMETRICAL ISOMERISM
aa baa
b
a
a
b
a
a
a
and are identical but not G.I.
aa ba
bb ab
andaa
can show G.I.
cbS.K.S
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Conditions for G.I :
GEOMETRICAL ISOMERISM
4. Different groups should be in one plane (Planarity)
1. example
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1 following types of compound
GEOMETRICAL ISOMERISM
1. following types of compound can show geometrical isomers :
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A. Compounds with C=C(Alkene )
GEOMETRICAL ISOMERISM
p ( )
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trans-2-Butene has lesser
GEOMETRICAL ISOMERISM
dipole moment than cis -2-butene.
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Cis has high B.P. than trans.
GEOMETRICAL ISOMERISM
gBut trans has high mp than cis.
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A Compounds with C=C
GEOMETRICAL ISOMERISM
p
O
C
O
OHH
C C
HCO
OOH
HCO
OH
C
O
OHC
OH
O
Fumaric Acid
C C
HH HH
Maleic Acid
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Maleic acid form Anhydride
GEOMETRICAL ISOMERISM
y
CCO
OH O
OH C CO
OO
C C
HH
CC
H H
Maleic Acid Maleicanhydride
Fumaric acid: No AnhydrideMaleic Acid y
HCO
OH
C C
HCO
CH OH
No anhydride
O
Fumaric Acid
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cis and trans 1,2-Dichloroethene
GEOMETRICAL ISOMERISM
,
Z: 1.28 g/cm³Boiling Z: 60.3 °CDensity
g/
E: 1.26 g/cm³
o g
point
60 3 C
E: 47.5 °C
Melting
point
Z: ‐81 °C
E: 81 °C
Dipole
t
Z (cis): 1.9
D
E (t ) 0point E: ‐81 C moment E (trans): 0
D
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cis and trans StilbeneGEOMETRICAL ISOMERISM
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cis and trans Stilbene
GEOMETRICAL ISOMERISM
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cis-Stilbene has a melting point GEOMETRICAL ISOMERISM
g pof 5-6 °C, while trans-stilbenemelts around 125 °C
CC H
C HCH
C HC H
H
C C
CC
C C H
CH C H
H
CHCHCH
CH C H
C H C H
CH
CH
CHCH
CHCHCH
CHCH
CHC
CH
C C
CCH
H H
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B. Compound with C=N bond
GEOMETRICAL ISOMERISM
p(imine, oxime )
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Compounds with C=N: Hydrazones
GEOMETRICAL ISOMERISM
p y
NNH2
CH3
CH
E-AcetaldehydehydrazoneNH2
NNH2
CH3
CH3
Z-Acetaldehydehydrazone
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Compounds with C=N: Phenyl
GEOMETRICAL ISOMERISM
p yhydrazones.
HNHC
CHCH
CH
Ph
CNCHCH
Ph
E-Benzaldehydephenylhydrazone
H
C
H
NC
CHCH
CHPhNHC
CHCH
CH
Z-Benzaldehydephenylhydrazone
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Compounds with C=N:
GEOMETRICAL ISOMERISM
pSemicarbazone
C
O
NHCH3
C N
NH NH2
H
O
C
O
N H 2H
C N
N H N H 2
CH 3
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C. Compounds with N=N (Azo)
GEOMETRICAL ISOMERISM
p ( )
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Compounds with N=N :
GEOMETRICAL ISOMERISM
pAzobenzene
CHCH CHCHCH
CH
CH
CH CH
CHCH
CH
CCH CHC
N N
CHCH
CH NC
CHCH
CCH
CHN
NC
CHCH
CH
CH
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D. Compounds with Cycles
GEOMETRICAL ISOMERISM
p y
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D Compounds with Cycles
GEOMETRICAL ISOMERISM
D Compounds with Cycles
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D. Compounds with Cycles
GEOMETRICAL ISOMERISM
p y
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D Compounds with Cycles
GEOMETRICAL ISOMERISM
p y
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E. Cyclooctene or higher alkene
GEOMETRICAL ISOMERISM
E. Cyclooctene or higher alkene
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F. Cumulene with odd no
GEOMETRICAL ISOMERISM
F. Cumulene with odd no
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G. Spirane with odd rings
GEOMETRICAL ISOMERISM
p g
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spirane with odd no of rings
GEOMETRICAL ISOMERISM
p g
trans Spiranetrans‐Spirane
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H. spiroallene with odd no of
GEOMETRICAL ISOMERISM
p( + rings)
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I. Decaline
GEOMETRICAL ISOMERISM
I. Decaline
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CONCEPT TESTING
GEOMETRICAL ISOMERISM
CONCEPT TESTING
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1 Is G I possible in given compound ?
GEOMETRICAL ISOMERISM
1. Is G.I. possible in given compound ?
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GEOMETRICAL ISOMERISM
2 Is G I possible in given compound ?2. Is G.I. possible in given compound ?
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GEOMETRICAL ISOMERISM
3 Is G I possible in given compound ?3. Is G.I. possible in given compound ?
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GEOMETRICAL ISOMERISM
4 Is G I possible in given compound ?4. Is G.I. possible in given compound ?
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GEOMETRICAL ISOMERISM
5 Is G I possible in given compound ?5. Is G.I. possible in given compound ?
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GEOMETRICAL ISOMERISM
6 Is G I possible in given compound ?
A. 1,2-dichloropropene
6. Is G.I. possible in given compound ?
B. 2,3- dichloro -1-butene
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GEOMETRICAL ISOMERISM
7 Is G I possible in given compound ?
A. 1,1-dichlorocyclopropaneB 1 2 –dichlorocyclopropane
7. Is G.I. possible in given compound ?
B. 1,2 –dichlorocyclopropaneC. 1,3-dichlorocyclohexene
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GEOMETRICAL ISOMERISM
Solution
1. Yes2 No
Solution
2. No3. No4. Yes5. No6. A Yes B No7. A No B Yes C No
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GEOMETRICAL ISOMERISM
Formation of Oxime.Formation of Oxime.Symmetrical aldehyde /ketone
form one oxime.
C
CH2
CH2
CH2
CH2
CH2 O N OHH
HC
CH2
CH2
CH2
CH2
CH2N
OH
22 2
sym ald/ketone only one oximeS.K.S
inha
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GEOMETRICAL ISOMERISM
Formation of OximeFormation of OximeSymmetrical aldehyde /ketone
form one oxime.Unsymmetrical aldehyde
/ketone form two oxime.
C
CHCH
CH O N OH
H
C
CHCH
CH2 N
OH
CH2CH2 OH
C
CH2CH2
CH2 O N OH
H
C
CH2CH2
CH2 N
CH2CH2 H
C
C 2
CH
C 2
CH
CH2 N
OH
unsym ald/ketone form two oxime
C
CHCH
CH2 O N OH
H
y S.K.S
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GEOMETRICAL ISOMERISM
Formation of OximeFormation of OximeUnsymmetrical aldehyde
/ketone form two oxime.
C
CH3
O N OH
H
C
CH3
N
OH
C
CH2CH3
O N OH
H
C
CH2CH3
N
CHCH
C
CH2
CH3
CH3
N
OH
C
CH2
CH3
CH3
O N OH
H
H
unsym ald/ketone form two oximeS.K.S
inha
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GEOMETRICAL ISOMERISM
Formation of HydrazoneFormation of HydrazoneUnsymmetrical aldehyde
/ketone form two
H H H NH2
Hydrazones.
C O
CH3
N NH2
H
C N
CH3
C N
NH2CH3
C
CH3
H
O N NH2
H
H
H
unsym ald/ketone form two hydra
H H
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GEOMETRICAL ISOMERISM
Formation of HydrazoneFormation of HydrazoneSymmetrical aldehyde /ketone
form one Hydrazone.
H H H NH2
C O
H
N NH2
H
C N
H
sym ald/ketoneform one hydra
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GEOMETRICAL ISOMERISM
Formation of OximeFormation of OximeSymmetrical aldehyde /ketone
form one oxime.
C
CH3
O N
H
H
OH C
CH3
N
OH
CHCH3 H CH3
sym ald/ketoneform one oximS.K
.Sinh
a
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GEOMETRICAL ISOMERISM
Nomenclature in G I
Cis / trans: similarity of groups1 Similar groups on the same
Nomenclature in G.I
1. Similar groups on the same side or nearest : cis
2. Similar groups on the opposite side or farthest : transS.K
.Sinh
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CONCEPT TESTING
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Q1 Are these two cis trans GEOMETRICAL ISOMERISM
isomers?
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GEOMETRICAL ISOMERISMQ2 Are these two cis trans isomers ?
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GEOMETRICAL ISOMERISMQ3 Are these two cis trans isomers ?
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GEOMETRICAL ISOMERISMQ4 Are these two cis trans isomers ?
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GEOMETRICAL ISOMERISMQ5 Are these two cis trans isomers ?
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GEOMETRICAL ISOMERISMQ6 Are these two cis trans isomers ?
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GEOMETRICAL ISOMERISMQ7 Are these two cis trans isomers ?
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GEOMETRICAL ISOMERISM
Q8 Relation between the given pair
Cl
Q8 Relation between the given pair of compound is …………………………..
C CH2
Cl
HHH
C C
CC
H
Cl HH H
Cl
CC
H
Cl
H
H
C CH2
Cl
HHCl
C C
CC
H
H HH H
CC
H
H
H
H
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GEOMETRICAL ISOMERISM
Q9 Relation between the given pair
Cl
Q9 Relation between the given pair of compound is …………………………..
C
C CH2
C
Cl
ClHH
C C
CCH HH H
H HCl
C CH2H
HH
C C
CC
H
Cl HH H
CC
H
Cl
H
H
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GEOMETRICAL ISOMERISM
Q10 Relation between the given pair Q10 Relation between the given pair of compound is …………………………..
CH2
CH3
C CH2CH3 C CH3
ClCl
CH
CH3
CH3CH2
CC
CH2CH3
Cl
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GEOMETRICAL ISOMERISM
Q11 Relation between the given pair Q11 Relation between the given pair of compound is …………………………..
CH3CH2
CH2CH
CHCH2
CH2CH3
CH3CH
CHCH2
CH2CH2
CH2CH3CH CH2 CH2 CH3
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GEOMETRICAL ISOMERISM
Q12 Relation between the given pair Q12 Relation between the given pair of compound is …………………………..
CH3CH2
CH2CH
CHCH3
CH3 CH CH2 CH3CH3CH
CHCH2
CH2CH2
CH3
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GEOMETRICAL ISOMERISM
Q13 Relation between the given pair
H
Q13 Relation between the given pair of compound is …………………………..
C H 2 C
H
CH 2
C H 2 C
C C H 2
C H 3 C H 3H
H
CH2 C CH2
H
CH3 C CH2 CH3
HH
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GEOMETRICAL ISOMERISM
Q14 Relation between the given pair
H
Q14 Relation between the given pair of compound is …………………………..
CHCH2
OCH2
CC
CHCH3 O C CH3
H
H
CH2 C
CH
O CH2 C H
CHCH3 CH3
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GEOMETRICAL ISOMERISM
Q15 Relation between the given pair
CH2 CH2
Q15 Relation between the given pair of compound is …………………………..
CH2CH CH
CH2
CH2C
CHC
H
H
H H
CH2 C CH CH
H
CHC
CCH2
CHCH2
H
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GEOMETRICAL ISOMERISM
Q16 Relation between the given pair
ClB
Q16 Relation between the given pair of compound is …………………………..
C CCl
ClBr
CH2
C
C
C
H HCH2 H
ClCl
C CH
ClCl
CH 2
CH
CH H
CH 2 Br
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GEOMETRICAL ISOMERISM
Q17 Relation between the given pair
C H 3
Q17 Relation between the given pair of compound is …………………………..
C HCH
CH C HC H
3
C H 2
C H 2
CH 2
CH 2
C H
C H 2C H 2C H 2
CH 2 C H 2C H 2
CH2
CH2CH2 CH
CH2 CH3
CHCH
CH2 CH2CHCH2 CH
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GEOMETRICAL ISOMERISM
Answer
1. No2. No3. No4. No4. No5. Yes6. No7. No7. No8. Geometrical8. Positional10 Geometrical10. Geometrical11. Positional12. Homologous13 Identical13. Identical14. Geometrical15. Geometrical16 Geometrical16. Geometrical17. Geometrical
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GEOMETRICAL ISOMERISM
Nomenclature in G I
Cis / trans: similarity of groups1 Similar groups on the same
Nomenclature in G.I
1. Similar groups on the same side or nearest : cis
2. Similar groups on the opposite side or farthest : transS.K
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GEOMETRICAL ISOMERISM
Nomenclature in G I
E and Z : Based on seniority Seniors /high priority groups on the
Nomenclature in G.I
Seniors /high priority groups on thesame side or nearest : Z
(Z = zusammen = together)
Seniors /high priority groups on the opposite side or farthest :E
(E = entgegen = opposite)S.K.S
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GEOMETRICAL ISOMERISM
Sequence rules : (CIP rules)
• Rules for seniority
Sequence rules : (CIP rules)
Rule I : Greater the atomic number of 1st atom , greater the senior group.
I > Br > Cl > S > F > O > N > C
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Sequence rules : (CIP rules)GEOMETRICAL ISOMERISM
Sequence rules : (CIP rules)
Rule II : If atomic number is same then isotopes with the greater mass no has greater priority .
Ex. (a) – T > – D > – H
(b) –C14H3 > – C12H3
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GEOMETRICAL ISOMERISM
Sequence rules : (CIP rules)Sequence rules : (CIP rules)
Rule III : If the first atom is identical than second atom is observed for seniority.
Ex. (a)– CH2Cl > – CH2OH > –CH2NH2 > –CH2CH3 > – CH3
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GEOMETRICAL ISOMERISM
Sequence rules : (CIP rules)Sequence rules : (CIP rules)
Rule IV : Groups containing double or triple bonds are assigned seniority as if the bonds are connected with
t tseparate atoms..
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GEOMETRICAL ISOMERISM
Sequence rules : (CIP rules)Sequence rules : (CIP rules)
Ex. for deciding seniority among – C ≡ C and – CH= CH2 , their h pothetical eq i alents arehypothetical equivalents are compared.
CH CH CCH3
CH3 CH CH2 CH3 C CH3H
CH3 C CH CH3 CCH3
CH33CH3S.K
.Sinh
a
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GEOMETRICAL ISOMERISM
Sequence rules : (CIP rules)Sequence rules : (CIP rules)
Rule V : Bond pair is senior to lone pair. H
NHHH
H
H N+
H
H
Greater Priority
H N+ H
Greater PriorityH
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CONCEPT TESTING
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GEOMETRICAL ISOMERISM
Q1 Check if the given compound is Q1 Check , if the given compound is Z or E.
CH3Cl
C C
CH3Cl
C C
CHB CHCH2Br CH3
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GEOMETRICAL ISOMERISM
Q2 Check if the given compound is Q2: Check , if the given compound is Z or E.
OH
CHNH2 CH3
OH
C C
2 3
CH2Br CH3
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GEOMETRICAL ISOMERISM
Q3 Check if the given compound is Q3: Check , if the given compound is Z or E.
CHCH3OH
CCH2
CH2 CH2
C
HCH2 CH2 HBr
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GEOMETRICAL ISOMERISM
Q4 Check if the given compound is Q4: Check , if the given compound is Z or E.
CH2
CHOH CH3
CH3
CCH2
CH2 CH2
C
CH3Br 3Br
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GEOMETRICAL ISOMERISM
Q5 Check if the given compound is Q5: Check , if the given compound is Z or E.
C CH
H
CH3
C
C
CH3
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GEOMETRICAL ISOMERISM
Q6 Check if the given compound is Q6: Check , if the given compound is Z or E.
CH CH
CH3
C C
CH2 C
CH CH
CH
CH2 C CHCl
CH CH
CH CHS.K.S
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GEOMETRICAL ISOMERISM
Q7 Check if the given compound is Q7: Check , if the given compound is Z or E.
O HCH 3
C NC N
H
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GEOMETRICAL ISOMERISM
Q8 Check if the given compound is Q8: Check , if the given compound is Z or E.
CH
CH
C
CH
OH
C
CH
CH
C OH
Cl
C C
C CHCH2
CH CH
CH CH
I
CH CH
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GEOMETRICAL ISOMERISM
Q9 Check if the given compound is
CH
Q9: Check , if the given compound is Z or E.
CCH CH
CH3
C C
CCH3 CH2
C C
CCH2CH3 CCH2
CH
CH3
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GEOMETRICAL ISOMERISM
Q10 Check if the given compound is Q10: Check , if the given compound is Z or E.
CCH CH
CH3
C
CH3
C C
CCH CH2C
CH3
CCH2
CH
CH2
CHCH CHCHCH2
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GEOMETRICAL ISOMERISM
Answer
1. Z2. E3. E4 E4. E5. E6. Z7. Z8. Z8 Z8. Z10. E
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Number of G I:
GEOMETRICAL ISOMERISM
Number of G I:
Numbers of geometricalNumbers of geometrical isomers can be found by calculating the number of gstereocenters in the compound.
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GEOMETRICAL ISOMERISM
Number of G I:
Step-1: Count total no of
Number of G I:
Step-1: Count total no. of possible stereocenterwhere GI is possible.
CH3CH
CHCH
CHCH
CHCH2
CHCH2
G.I not possibleG.I possibleS.K.S
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GEOMETRICAL ISOMERISM
Number of G I:
Step-2: See if both ends are
Number of G I:
Step-2: See if both ends are identical or not.
If both ends are not identical then total no of possible GI = 2n ,
where n= no of stereo-centers.S.K
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GEOMETRICAL ISOMERISM
Number of G I:
Step-2: See if both ends are
Number of G I:
Step-2: See if both ends are identical or not.
If both ends are not identical then total no of possible GI = 2n ,
where n= no of stereo-centers.S.K
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GEOMETRICAL ISOMERISM
If both ends are not identical then total no of possible GI = 2n , where n= no of stereocentersstereocenters.
CH3CH
CHCH
CHCH
CHCH2
CHCH2C 2 2
Here n=3
G.I not possibleG.I possible
Total no of GI = 23 =8
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GEOMETRICAL ISOMERISM
Step-i: if both ends are identical .Then see if the no of possibleno 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)
CH C H C H C H C HCH 3C H
C HC H
C HC H
C HC H
C HC H 3
Here n=4
G.I possible
Total no of GI = 10
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GEOMETRICAL ISOMERISM
Step-i: if both ends are identical .Then see if the no of possibleno 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)
CH3CH2
CHCH
CHCH
CHCH
CH2CH3
G I ibl
Here n=3 Total no of GI = 6
G.I possible
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CONCEPT TESTING
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GEOMETRICAL ISOMERISM
Q:1 Find total no of geometrical isomer for
CHCH3
CCH
CHCH
CH
CH
CH2
CHCH
CCH2
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GEOMETRICAL ISOMERISM
Q:2 Find total no of geometrical isomer for
H
C HC H 2
CH 2
C HC
CH 2 C l
H
C H 2C
C HC H 2
C H
C H 2
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GEOMETRICAL ISOMERISM
Q:3 Find total no of geometrical isomer for
C
HCH3
CHCH
CH2
CHC
CH3
CH2C
2
CCH3
3
CH3
CCH3
CH22S.K.S
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GEOMETRICAL ISOMERISM
Q:4 Find total no of geometrical isomer for
C H 3
C H 2
C HC H
CH 32
CC
CCH 3
CH 3 C H 3
CCH 3
N H
C H 3
N HS.K.S
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GEOMETRICAL ISOMERISM
Q:5 Find total no of geometrical isomer for
CH3
CH2 CH C C CH CH CH CH3
CH3
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GEOMETRICAL ISOMERISM
Q:6 How many products are formed in given reaction
O
C
O
+NH2
OH
CH3 CH3
Q 7 H d t f dQ:7 How many products are formed in given reaction
O
+NH2
OHCH2
CCH2 +
CH2CH2
CH22
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GEOMETRICAL ISOMERISM
Q:8 How many products are formed in given reaction
O
C
O
CH2
C
CH2
CH2+
NH2 NH2
CH22
O
Q:9 How many products are formed inQ:9 How many products are formed in given reaction
C
O
CH3 C
CH2
+ NH2 OH
CH3
CCH3 CH3
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GEOMETRICAL ISOMERISM
10. How many products are formed in given reaction
C
CH
CH2CH2
C
O
+
NH2 OH
CH2C
C
O
O
O
11. How many products are formed in given reaction
CCH2
COO
NH2 OH
CH2C
CH2
CH2
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GEOMETRICAL ISOMERISM
12 Write all Isomers of C H12.Write all Isomers of C4H8
13.Write all Isomers of C5H10
14.Write all GI of C2HClBr2
15 Write all GI of C HClBrI15.Write all GI of C2HClBrI
16.Write G.I of 1,3,5,7‐Octatetraene
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