Revision of isomerism Revision of isomerism Revision of isomerism Revision of isomerism

1.Structural isomerism 1.Structural isomerism

2. Geometrical isomerism 2. Geometrical isomerism
3.Optical isomerism 3.Optical isomerism
4. Conformational isomerism 4. Conformational isomerism
By By
Ajnish Ajnish Kumar Gupta (AKG) Kumar Gupta (AKG)
Lecturer of Organic Chemistry Lecturer of Organic Chemistry
Ajnish@OrganicChemistry.co.in Ajnish@OrganicChemistry.co.in
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Isomers Isomers
Two or more molecules with same molecular formula but have different Two or more molecules with same molecular formula but have different
physical & chemical properties physical & chemical properties
Isomers Isomers
Two or more molecules with same molecular formula but have different Two or more molecules with same molecular formula but have different
physical & chemical properties physical & chemical properties
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Isomers Isomers
Structural
i.e Compounds have different IUPAC name
Structural
i.e Compounds have different IUPAC name
Chain Chain Positional Positional Functional Functional Metamer Metamer Tautomer Tautomer
Stereo
i.e. Compounds having same IUPAC name
Stereo
i.e. Compounds having same IUPAC name
Configuration Configuration Conformation Conformation
Structural isomerism Structural isomerism
Chain isomerism : Chain isomerism :
Isomers which differ in main chain or side chain of carbon keeping no Isomers which differ in main chain or side chain of carbon keeping no
change in nature of chemical reaction, functional groups, multiple bonds change in nature of chemical reaction, functional groups, multiple bonds
or or substituents substituents..
Position isomerism : Position isomerism :
Isomers which differ in position of functional groups, multiple bonds or Isomers which differ in position of functional groups, multiple bonds or
substituents substituents keeping no change in main skeleton or side skeleton of keeping no change in main skeleton or side skeleton of
carbon, functional groups or multiple bonds. carbon, functional groups or multiple bonds.
Functional isomerism : Functional isomerism :
Isomers which differ in nature of chemical reactions i.e. mainly Isomers which differ in nature of chemical reactions i.e. mainly
functional groups. functional groups.
Metamerism Metamerism ::
Isomers which have any type of difference in carbon along the Isomers which have any type of difference in carbon along the
polyvalent atom containing functional groups which have carbon in both polyvalent atom containing functional groups which have carbon in both
sides. sides.
Tautomerism Tautomerism ::
Isomers which differ in position of protons when two structures are in Isomers which differ in position of protons when two structures are in
dynamic equilibrium with each others dynamic equilibrium with each others
Structural isomerism Structural isomerism
Chain isomerism : Chain isomerism :
Isomers which differ in main chain or side chain of carbon keeping no Isomers which differ in main chain or side chain of carbon keeping no
change in nature of chemical reaction, functional groups, multiple bonds change in nature of chemical reaction, functional groups, multiple bonds
or or substituents substituents..
Position isomerism : Position isomerism :
Isomers which differ in position of functional groups, multiple bonds or Isomers which differ in position of functional groups, multiple bonds or
substituents substituents keeping no change in main skeleton or side skeleton of keeping no change in main skeleton or side skeleton of
carbon, functional groups or multiple bonds. carbon, functional groups or multiple bonds.
Functional isomerism : Functional isomerism :
Isomers which differ in nature of chemical reactions i.e. mainly Isomers which differ in nature of chemical reactions i.e. mainly
functional groups. functional groups.
Metamerism Metamerism ::
Isomers which have any type of difference in carbon along the Isomers which have any type of difference in carbon along the
polyvalent atom containing functional groups which have carbon in both polyvalent atom containing functional groups which have carbon in both
sides. sides.
Tautomerism Tautomerism ::
Isomers which differ in position of protons when two structures are in Isomers which differ in position of protons when two structures are in
dynamic equilibrium with each others dynamic equilibrium with each others
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Geometrical isomerism Geometrical isomerism
Isomers which are formed by restriction in rotation in a molecule. Isomers which are formed by restriction in rotation in a molecule.
Conditions: Conditions:
1. Molecules must have restriction in rotation 1. Molecules must have restriction in rotation
2. Restricted atoms must have different 2. Restricted atoms must have different substituents substituents attach to them attach to them
General cases of Geometrical isomerism : General cases of Geometrical isomerism :
1. Along C=C bond 1. Along C=C bond
2. Along C=N bond 2. Along C=N bond
3. Along N=N bond 3. Along N=N bond
4. Along 4. Along cycloalkanes cycloalkanes
5. Along 5. Along cycloalkenes cycloalkenes with carbon 8 or greater than 8 with carbon 8 or greater than 8
Some molecules have restriction in rotation but due to Some molecules have restriction in rotation but due to
absence of different absence of different substituents substituents they dont show GI they dont show GI
1. Along C=O bond 1. Along C=O bond
2. Along O=O bond 2. Along O=O bond
3. Along N=O bond 3. Along N=O bond
4. Along S=O bond 4. Along S=O bond
5. Along C 5. Along CC bond C bond
6. Along C 6. Along CN bond N bond
Geometrical isomerism Geometrical isomerism
Isomers which are formed by restriction in rotation in a molecule. Isomers which are formed by restriction in rotation in a molecule.
Conditions: Conditions:
1. Molecules must have restriction in rotation 1. Molecules must have restriction in rotation
2. Restricted atoms must have different 2. Restricted atoms must have different substituents substituents attach to them attach to them
General cases of Geometrical isomerism : General cases of Geometrical isomerism :
1. Along C=C bond 1. Along C=C bond
2. Along C=N bond 2. Along C=N bond
3. Along N=N bond 3. Along N=N bond
4. Along 4. Along cycloalkanes cycloalkanes
5. Along 5. Along cycloalkenes cycloalkenes with carbon 8 or greater than 8 with carbon 8 or greater than 8
Some molecules have restriction in rotation but due to Some molecules have restriction in rotation but due to
absence of different absence of different substituents substituents they dont show GI they dont show GI
1. Along C=O bond 1. Along C=O bond
2. Along O=O bond 2. Along O=O bond
3. Along N=O bond 3. Along N=O bond
4. Along S=O bond 4. Along S=O bond
5. Along C 5. Along CC bond C bond
6. Along C 6. Along CN bond N bond
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Nomenclature used in GI Nomenclature used in GI
Cis Cis- -Trans: Trans:
Mainly used for C=C bonds & Mainly used for C=C bonds & Cycloalkanes Cycloalkanes
Cis Cis : when 2 similar groups are on the same side of restricted atoms : when 2 similar groups are on the same side of restricted atoms
Trans : when 2 similar groups are on the same side of restricted atoms Trans : when 2 similar groups are on the same side of restricted atoms
Syn Syn- -Anti: Anti:
Mainly used for C=N & N=N bonds Mainly used for C=N & N=N bonds
Syn Syn : When H & groups are on the same side of restricted atoms when : When H & groups are on the same side of restricted atoms when
derived from derived from aldehydes aldehydes..
When both lone pairs of electrons are on the same side of restricted When both lone pairs of electrons are on the same side of restricted
atoms in N=N bonded compounds. atoms in N=N bonded compounds.
Anti : When H & groups are on the opposite side of restricted atoms Anti : When H & groups are on the opposite side of restricted atoms
when derived from when derived from aldehydes aldehydes..
When both lone pairs of electrons are on the opposite side of When both lone pairs of electrons are on the opposite side of
restricted atoms in N=N bonded compounds. restricted atoms in N=N bonded compounds.
In case of molecules with C=N we have to specify the group on which In case of molecules with C=N we have to specify the group on which
we are saying about we are saying about syn syn or anti. or anti.
EE- -Z : Z :
Next page Next page
Nomenclature used in GI Nomenclature used in GI
Cis Cis- -Trans: Trans:
Mainly used for C=C bonds & Mainly used for C=C bonds & Cycloalkanes Cycloalkanes
Cis Cis : when 2 similar groups are on the same side of restricted atoms : when 2 similar groups are on the same side of restricted atoms
Trans : when 2 similar groups are on the same side of restricted atoms Trans : when 2 similar groups are on the same side of restricted atoms
Syn Syn- -Anti: Anti:
Mainly used for C=N & N=N bonds Mainly used for C=N & N=N bonds
Syn Syn : When H & groups are on the same side of restricted atoms when : When H & groups are on the same side of restricted atoms when
derived from derived from aldehydes aldehydes..
When both lone pairs of electrons are on the same side of restricted When both lone pairs of electrons are on the same side of restricted
atoms in N=N bonded compounds. atoms in N=N bonded compounds.
Anti : When H & groups are on the opposite side of restricted atoms Anti : When H & groups are on the opposite side of restricted atoms
when derived from when derived from aldehydes aldehydes..
When both lone pairs of electrons are on the opposite side of When both lone pairs of electrons are on the opposite side of
restricted atoms in N=N bonded compounds. restricted atoms in N=N bonded compounds.
In case of molecules with C=N we have to specify the group on which In case of molecules with C=N we have to specify the group on which
we are saying about we are saying about syn syn or anti. or anti.
EE- -Z : Z :
Next page Next page
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EE- -Z : Z :
IUPAC recommended nomenclature used for all geometrical isomers IUPAC recommended nomenclature used for all geometrical isomers
Given by Cahn Given by Cahn- -Ingold Ingold- -Prelog therefore priority rule for deciding Prelog therefore priority rule for deciding
configuration as E or Z is called as CIP Rule. configuration as E or Z is called as CIP Rule.
If two high priority groups are on the same side of restricted atoms If two high priority groups are on the same side of restricted atoms
than such configuration is called as Z. than such configuration is called as Z.
If two high priority groups are on the opposite side of restricted atoms If two high priority groups are on the opposite side of restricted atoms
than such configuration is called as E. than such configuration is called as E.
CIP Rule : CIP Rule :
1. Group with the first atom having high atomic number directly attach 1. Group with the first atom having high atomic number directly attach
to restricted atom in case of GI is given higher priority. to restricted atom in case of GI is given higher priority.
2. If the first atom is identical then second atom is observed for 2. If the first atom is identical then second atom is observed for
deciding the priority. If second is also same then go on up to that deciding the priority. If second is also same then go on up to that
place from where we get the difference. place from where we get the difference.
3. If the group has 3. If the group has unsaturation unsaturation, then a hypothetical equivalent sigma , then a hypothetical equivalent sigma
bond is drawn for it and then compare with other group for seniority. bond is drawn for it and then compare with other group for seniority.
4. Only in case of isotopes where atomic number is same but have 4. Only in case of isotopes where atomic number is same but have
different atomic mass, atomic mass is given higher priority. different atomic mass, atomic mass is given higher priority.
Never correlate Never correlate Cis Cis- -Trans with E Trans with E- -Z because both have different Z because both have different
concepts for naming configurations. concepts for naming configurations.
CIP Rule is also used to decide R CIP Rule is also used to decide R- -S S nomenclatue nomenclatue in optical isomerism. in optical isomerism.
EE- -Z : Z :
IUPAC recommended nomenclature used for all geometrical isomers IUPAC recommended nomenclature used for all geometrical isomers
Given by Cahn Given by Cahn- -Ingold Ingold- -Prelog therefore priority rule for deciding Prelog therefore priority rule for deciding
configuration as E or Z is called as CIP Rule. configuration as E or Z is called as CIP Rule.
If two high priority groups are on the same side of restricted atoms If two high priority groups are on the same side of restricted atoms
than such configuration is called as Z. than such configuration is called as Z.
If two high priority groups are on the opposite side of restricted atoms If two high priority groups are on the opposite side of restricted atoms
than such configuration is called as E. than such configuration is called as E.
CIP Rule : CIP Rule :
1. Group with the first atom having high atomic number directly attach 1. Group with the first atom having high atomic number directly attach
to restricted atom in case of GI is given higher priority. to restricted atom in case of GI is given higher priority.
2. If the first atom is identical then second atom is observed for 2. If the first atom is identical then second atom is observed for
deciding the priority. If second is also same then go on up to that deciding the priority. If second is also same then go on up to that
place from where we get the difference. place from where we get the difference.
3. If the group has 3. If the group has unsaturation unsaturation, then a hypothetical equivalent sigma , then a hypothetical equivalent sigma
bond is drawn for it and then compare with other group for seniority. bond is drawn for it and then compare with other group for seniority.
4. Only in case of isotopes where atomic number is same but have 4. Only in case of isotopes where atomic number is same but have
different atomic mass, atomic mass is given higher priority. different atomic mass, atomic mass is given higher priority.
Never correlate Never correlate Cis Cis- -Trans with E Trans with E- -Z because both have different Z because both have different
concepts for naming configurations. concepts for naming configurations.
CIP Rule is also used to decide R CIP Rule is also used to decide R- -S S nomenclatue nomenclatue in optical isomerism. in optical isomerism.
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Optical isomerism: Optical isomerism:
Experimental background Experimental background : Those compounds which can rotate the plane : Those compounds which can rotate the plane
polarized light to certain angle is called optically active compounds and polarized light to certain angle is called optically active compounds and
the isomers are called as optical isomers. the isomers are called as optical isomers.
Theeoratical Theeoratical background : background : Chirality Chirality is one & sufficient condition for a is one & sufficient condition for a
molecule to be optically active molecule to be optically active..
Chirality Chirality means dissymmetry or means dissymmetry or nonsuperimposability nonsuperimposability of an object on its of an object on its
mirror image i.e. absence of plane of symmetry (POS) & Centre of mirror image i.e. absence of plane of symmetry (POS) & Centre of
symmetry (COS) . symmetry (COS) .
Dont confuse with Dont confuse with chiral chiral molecule and molecule and chiral chiral carbon, both are carbon, both are
different different
Chiral Chiral carbon is that carbon whose all the four carbon is that carbon whose all the four valencies valencies are different are different
but but chiral chiral molecule is that one which do not have POS & COS. molecule is that one which do not have POS & COS.
Symmetric molecules are some times called as Symmetric molecules are some times called as achiral achiral molecules so if a molecules so if a
carbon have carbon have atleast atleast 2 similar groups then it is 2 similar groups then it is achiral achiral carbon. carbon.
Plane of Symmetry (POS): Plane of Symmetry (POS): An imaginary plane that bisects a molecule An imaginary plane that bisects a molecule
in such a way that the two halves of the molecule are mirror images of in such a way that the two halves of the molecule are mirror images of
each other each other
Centre of Symmetry (COS): Centre of Symmetry (COS): It is the point in the centre of molecule It is the point in the centre of molecule
from which if we move in equal and opposite direction, we get the same from which if we move in equal and opposite direction, we get the same
atoms or groups on other side. atoms or groups on other side.
Optical isomerism: Optical isomerism:
Experimental background Experimental background : Those compounds which can rotate the plane : Those compounds which can rotate the plane
polarized light to certain angle is called optically active compounds and polarized light to certain angle is called optically active compounds and
the isomers are called as optical isomers. the isomers are called as optical isomers.
Theeoratical Theeoratical background : background : Chirality Chirality is one & sufficient condition for a is one & sufficient condition for a
molecule to be optically active molecule to be optically active..
Chirality Chirality means dissymmetry or means dissymmetry or nonsuperimposability nonsuperimposability of an object on its of an object on its
mirror image i.e. absence of plane of symmetry (POS) & Centre of mirror image i.e. absence of plane of symmetry (POS) & Centre of
symmetry (COS) . symmetry (COS) .
Dont confuse with Dont confuse with chiral chiral molecule and molecule and chiral chiral carbon, both are carbon, both are
different different
Chiral Chiral carbon is that carbon whose all the four carbon is that carbon whose all the four valencies valencies are different are different
but but chiral chiral molecule is that one which do not have POS & COS. molecule is that one which do not have POS & COS.
Symmetric molecules are some times called as Symmetric molecules are some times called as achiral achiral molecules so if a molecules so if a
carbon have carbon have atleast atleast 2 similar groups then it is 2 similar groups then it is achiral achiral carbon. carbon.
Plane of Symmetry (POS): Plane of Symmetry (POS): An imaginary plane that bisects a molecule An imaginary plane that bisects a molecule
in such a way that the two halves of the molecule are mirror images of in such a way that the two halves of the molecule are mirror images of
each other each other
Centre of Symmetry (COS): Centre of Symmetry (COS): It is the point in the centre of molecule It is the point in the centre of molecule
from which if we move in equal and opposite direction, we get the same from which if we move in equal and opposite direction, we get the same
atoms or groups on other side. atoms or groups on other side.
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Basic concepts & pictures Basic concepts & pictures
ss
Basic concepts & pictures Basic concepts & pictures
ss
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Chiral molecule - has
the property of
handedness i.e Not
superposable on its
mirror image
They can exist as a
pair of enantiomers
which are individually
a chiral molecule.
Achiral molecule -
has property of
Superposable on its
mirror image.
Mirror images = handedness
Left hand cannot be superimposed
on the right hand
Mirror image =
converts right hand
into left
Some terms used in optical isomerism Some terms used in optical isomerism
Enantiomers Enantiomers : : Two stereo isomers which are non Two stereo isomers which are non superimposable superimposable but are but are
mirror images of one another. mirror images of one another.
They have same physical properties so have 1 fraction on They have same physical properties so have 1 fraction on distilation distilation..
Diastereomers Diastereomers : : Two stereo isomers which are non Two stereo isomers which are non superimposable superimposable and non and non
mirror images of one another. mirror images of one another.
They have different physical properties so have 2 fractions on They have different physical properties so have 2 fractions on distilation distilation. .
Racemic Racemic mixture : mixture : Mixture of pair of Mixture of pair of enantiomers enantiomers in equal amounts. in equal amounts.
Compound is optically inactive due to external Compound is optically inactive due to external compansation compansation..
Meso Meso compound : compound : Indivisual Indivisual compound which have plane of symmetry along compound which have plane of symmetry along
with with chiral chiral centre. centre.
Compound is optically inactive due to internal Compound is optically inactive due to internal compansation compansation..
Specific rotation : Specific rotation : Observed rotation/Concentration Observed rotation/Concentration lenght lenght
Optical purity (OP): Optical purity (OP): Observed optical rotation/Optical rotation of pure Observed optical rotation/Optical rotation of pure
enatiomer enatiomer 100 100
Enantiomeric Enantiomeric excess (EE): excess (EE): Excess of one Excess of one enantiomer enantiomer over other/Entire over other/Entire
mixture mixture 100 100
Mathematically Mathematically optical purity (OP) = optical purity (OP) =enantiomeric enantiomeric excess (EE) excess (EE)
Resolution : Resolution : It is a chemical method to separate pair of It is a chemical method to separate pair of enantiomers enantiomers. .
In this method In this method enantiomers enantiomers ore first converted into ore first converted into diastereomers diastereomers by by
reacting with a compound which have reacting with a compound which have chiral chiral carbon and then distill them. carbon and then distill them.
Some terms used in optical isomerism Some terms used in optical isomerism
Enantiomers Enantiomers : : Two stereo isomers which are non Two stereo isomers which are non superimposable superimposable but are but are
mirror images of one another. mirror images of one another.
They have same physical properties so have 1 fraction on They have same physical properties so have 1 fraction on distilation distilation..
Diastereomers Diastereomers : : Two stereo isomers which are non Two stereo isomers which are non superimposable superimposable and non and non
mirror images of one another. mirror images of one another.
They have different physical properties so have 2 fractions on They have different physical properties so have 2 fractions on distilation distilation. .
Racemic Racemic mixture : mixture : Mixture of pair of Mixture of pair of enantiomers enantiomers in equal amounts. in equal amounts.
Compound is optically inactive due to external Compound is optically inactive due to external compansation compansation..
Meso Meso compound : compound : Indivisual Indivisual compound which have plane of symmetry along compound which have plane of symmetry along
with with chiral chiral centre. centre.
Compound is optically inactive due to internal Compound is optically inactive due to internal compansation compansation..
Specific rotation : Specific rotation : Observed rotation/Concentration Observed rotation/Concentration lenght lenght
Optical purity (OP): Optical purity (OP): Observed optical rotation/Optical rotation of pure Observed optical rotation/Optical rotation of pure
enatiomer enatiomer 100 100
Enantiomeric Enantiomeric excess (EE): excess (EE): Excess of one Excess of one enantiomer enantiomer over other/Entire over other/Entire
mixture mixture 100 100
Mathematically Mathematically optical purity (OP) = optical purity (OP) =enantiomeric enantiomeric excess (EE) excess (EE)
Resolution : Resolution : It is a chemical method to separate pair of It is a chemical method to separate pair of enantiomers enantiomers. .
In this method In this method enantiomers enantiomers ore first converted into ore first converted into diastereomers diastereomers by by
reacting with a compound which have reacting with a compound which have chiral chiral carbon and then distill them. carbon and then distill them.
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Some Some chiral chiral molecules without molecules without chiral chiral carbon carbon
1. 1. Allenes Allenes with even no of double bonds & end with even no of double bonds & end cabon cabon have different have different
substituents substituents..
2. 2. Spiranes Spiranes with even no of rings & end with even no of rings & end cabon cabon have different have different substituents substituents
3. 3. Cycloalkylidines Cycloalkylidines with some of double bonds & rings are even in no and with some of double bonds & rings are even in no and
end end cabon cabon have different have different substituents substituents..
4. Ortho 4. Ortho- -ortho ortho tetra substituted biphenyl with two different substituent tetra substituted biphenyl with two different substituent
at at ortho ortho position of one phenyl group. position of one phenyl group.
5. Quaternary ammonium salt with all the four 5. Quaternary ammonium salt with all the four valancies valancies are different. are different.
6. Tetravalent phosphorus compounds in which all its four 6. Tetravalent phosphorus compounds in which all its four valancies valancies are are
different. different.
7. Tetravalent 7. Tetravalent sulphur sulphur compounds in which all its four compounds in which all its four valancies valancies are are
different. different.
8. Tetravalent silicon compounds in which all its four 8. Tetravalent silicon compounds in which all its four valancies valancies are are
different. different.
9. Tetravalent germanium compounds in which all its four 9. Tetravalent germanium compounds in which all its four valancies valancies are are
different. different.
10. Any tetravalent compounds in which all its four 10. Any tetravalent compounds in which all its four valancies valancies are different. are different.
Basic for a compound to show optical activity is Basic for a compound to show optical activity is
nonsuperimposability nonsuperimposability i.e. absence of Plane of symmetry & Centre i.e. absence of Plane of symmetry & Centre
of symmetry. of symmetry.
Some Some chiral chiral molecules without molecules without chiral chiral carbon carbon
1. 1. Allenes Allenes with even no of double bonds & end with even no of double bonds & end cabon cabon have different have different
substituents substituents..
2. 2. Spiranes Spiranes with even no of rings & end with even no of rings & end cabon cabon have different have different substituents substituents
3. 3. Cycloalkylidines Cycloalkylidines with some of double bonds & rings are even in no and with some of double bonds & rings are even in no and
end end cabon cabon have different have different substituents substituents..
4. Ortho 4. Ortho- -ortho ortho tetra substituted biphenyl with two different substituent tetra substituted biphenyl with two different substituent
at at ortho ortho position of one phenyl group. position of one phenyl group.
5. Quaternary ammonium salt with all the four 5. Quaternary ammonium salt with all the four valancies valancies are different. are different.
6. Tetravalent phosphorus compounds in which all its four 6. Tetravalent phosphorus compounds in which all its four valancies valancies are are
different. different.
7. Tetravalent 7. Tetravalent sulphur sulphur compounds in which all its four compounds in which all its four valancies valancies are are
different. different.
8. Tetravalent silicon compounds in which all its four 8. Tetravalent silicon compounds in which all its four valancies valancies are are
different. different.
9. Tetravalent germanium compounds in which all its four 9. Tetravalent germanium compounds in which all its four valancies valancies are are
different. different.
10. Any tetravalent compounds in which all its four 10. Any tetravalent compounds in which all its four valancies valancies are different. are different.
Basic for a compound to show optical activity is Basic for a compound to show optical activity is
nonsuperimposability nonsuperimposability i.e. absence of Plane of symmetry & Centre i.e. absence of Plane of symmetry & Centre
of symmetry. of symmetry.
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Calculation for number of Calculation for number of sterioisomers sterioisomers
Case 1 : Case 1 : For For unsymmertical unsymmertical molecules with n molecules with n stereocentres stereocentres
No. of stereo isomers = No. of stereo isomers = 2 2
n n
Case 2 : Case 2 : For For Symmertical Symmertical molecules with n even molecules with n even stereocentres stereocentres
No. of stereo isomers = No. of stereo isomers = 2 2
n n 1 1
+ + 2 2
n/2 n/2 1 1
Case 3 : Case 3 : For For Symmertical Symmertical molecules with n odd molecules with n odd stereocentres stereocentres
Case a : Case a : Central stereo centre is optical in nature : Central stereo centre is optical in nature :
No. of stereo isomers = No. of stereo isomers = 2 2
n n 1 1
+ + 2 2
n n 1/2 1/2
Case b : Case b : Central stereo centre is geometrical in nature : Central stereo centre is geometrical in nature :
No. of stereo isomers = No. of stereo isomers = 2 2
n n 1 1
It is important to remember that It is important to remember that stereocentres stereocentres means means
any centre along which we can see stereo isomerism i.e. any centre along which we can see stereo isomerism i.e.
Optical or geometrical both. Optical or geometrical both.
It may be along C=C,C=N,N= It may be along C=C,C=N,N=N,Cycloalkanes N,Cycloalkanes, , Cycloalkenes Cycloalkenes with with
8 8 of geometrical or along of geometrical or along chiral chiral carbon, pseudo carbon, pseudo chiral chiral carbon or carbon or
along special case of along special case of allenes allenes, , spiranes spiranes, , cycloalkylidine cycloalkylidine or or ortho ortho- -
ortho ortho tetra substituted biphenyl. tetra substituted biphenyl.
Calculation for number of Calculation for number of sterioisomers sterioisomers
Case 1 : Case 1 : For For unsymmertical unsymmertical molecules with n molecules with n stereocentres stereocentres
No. of stereo isomers = No. of stereo isomers = 2 2
n n
Case 2 : Case 2 : For For Symmertical Symmertical molecules with n even molecules with n even stereocentres stereocentres
No. of stereo isomers = No. of stereo isomers = 2 2
n n 1 1
+ + 2 2
n/2 n/2 1 1
Case 3 : Case 3 : For For Symmertical Symmertical molecules with n odd molecules with n odd stereocentres stereocentres
Case a : Case a : Central stereo centre is optical in nature : Central stereo centre is optical in nature :
No. of stereo isomers = No. of stereo isomers = 2 2
n n 1 1
+ + 2 2
n n 1/2 1/2
Case b : Case b : Central stereo centre is geometrical in nature : Central stereo centre is geometrical in nature :
No. of stereo isomers = No. of stereo isomers = 2 2
n n 1 1
It is important to remember that It is important to remember that stereocentres stereocentres means means
any centre along which we can see stereo isomerism i.e. any centre along which we can see stereo isomerism i.e.
Optical or geometrical both. Optical or geometrical both.
It may be along C=C,C=N,N= It may be along C=C,C=N,N=N,Cycloalkanes N,Cycloalkanes, , Cycloalkenes Cycloalkenes with with
8 8 of geometrical or along of geometrical or along chiral chiral carbon, pseudo carbon, pseudo chiral chiral carbon or carbon or
along special case of along special case of allenes allenes, , spiranes spiranes, , cycloalkylidine cycloalkylidine or or ortho ortho- -
ortho ortho tetra substituted biphenyl. tetra substituted biphenyl.
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Some compounds showing either Some compounds showing either GI,OI,both GI,OI,both or none or none Some compounds showing either Some compounds showing either GI,OI,both GI,OI,both or none or none
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Some compounds showing either Some compounds showing either GI,OI,both GI,OI,both or none or none Some compounds showing either Some compounds showing either GI,OI,both GI,OI,both or none or none
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Some compounds showing either Some compounds showing either GI,OI,both GI,OI,both or none or none Some compounds showing either Some compounds showing either GI,OI,both GI,OI,both or none or none
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Some compounds showing either Some compounds showing either GI,OI,both GI,OI,both or none or none Some compounds showing either Some compounds showing either GI,OI,both GI,OI,both or none or none
www.OrganicChemistry.co.in
Some compounds showing either Some compounds showing either GI,OI,both GI,OI,both or none or none Some compounds showing either Some compounds showing either GI,OI,both GI,OI,both or none or none
www.OrganicChemistry.co.in
Some compounds showing either Some compounds showing either GI,OI,both GI,OI,both or none or none Some compounds showing either Some compounds showing either GI,OI,both GI,OI,both or none or none
www.OrganicChemistry.co.in
Some compounds showing either Some compounds showing either GI,OI,both GI,OI,both or none or none Some compounds showing either Some compounds showing either GI,OI,both GI,OI,both or none or none
www.OrganicChemistry.co.in
Some compounds showing either Some compounds showing either GI,OI,both GI,OI,both or none or none Some compounds showing either Some compounds showing either GI,OI,both GI,OI,both or none or none
www.OrganicChemistry.co.in
Some compounds showing either Some compounds showing either GI,OI,both GI,OI,both or none or none Some compounds showing either Some compounds showing either GI,OI,both GI,OI,both or none or none
www.OrganicChemistry.co.in