Lec 5,6,7 Isomers

isomers
Isomers
• Isomers are compounds that have the same molecular

formula but different structures.
• There are mainly two types of isomers

– Constitutional isomers
• Different compounds that have the same molecular formula but
differ in the sequence in which their atoms are bonded
(connectivity).
– Stereo isomers
• Different compounds that have the same molecular formula and
connectivity but different arrangements of atoms in three-
dimensional space.
Constitutional isomers
• Constitutional isomers are generally subdivided
into three groups.
– chain isomers
– position isomers
– functional group isomers
• These subdivisions can overlap.

Continues….
• Chain isomers are those which have different
hydrocarbon chains for same molecular formula.
• Position isomers are those which have the same

functional group and/or substituents in different
positions in the same carbon chain.
• Functional group isomers are those which have

different functional groups in compounds having
the same molecular formula
• Draw all the possible constitutional isomers of
C5H10O
Activity 2; identify the category which the given set of isomers
are belongs to.
• C and E are
– Chain isomers to each
other
• A and B are
– Position isomers to
each other
• B, C, and D are
– Functional group
isomers to each other
• D and G are
each other
• G and H are
each other
Stereoisomers
• Stereoisomers
• Different compounds that have the same molecular
formula and connectivity but different arrangements
of atoms in three-dimensional space.
• There are two types of stereoisomers

• Enantiomers
– Enantiomers are stereoisomers whose molecules are
non-superimposable mirror images of each other.
• Diastereomers
– Diastereomers are stereoisomers whose molecules
are not mirror images of each other.
Chiral molecules
• What is a chiral molecule?

• A molecule having a chiral center is considered as a chiral
molecule.
• What is a chiral center?
▪ A tetrahedral carbon atom which is bonded to four different
groups is called as chiral center
A molecule having a tetrahedral carbon atom

which is bonded to four different groups is
considered as a chiral molecule.
Enantiomers
• If we consider a chiral
molecule, its mirror image
cannot superimpose on it.
• Therefore that chiral

molecule and its mirror
image are enantiomers to
each other.
chiral molecule and its mirror

image are enantiomers to each
other
If molecule is achiral….?
• If the molecule is achiral then there is a one mirror plane which
gives a mirror image which can superimpose on original.
Therefore cannot consider as enantiomers
Naming the enantiomers
• As enantiomers are two different molecules, therefore

each enantiomer should have a distinct name.
• R-S system or Cahn-Ingold-Prelog system is a part of the

IUPAC rules which is developed to differentiate the
enantiomers by name.
• If we have a chiral center in the molecule, we have to put

a label (R) or (S) before their name to differentiate the
enantiomers.
– Eg: (R)-2-butanol and (S)-2-butanol
How to assign R and S configurations
• After following the given three steps you can assign the
label.
1. Assign a priority (a, b, c, and d) for each of the four groups
attached to the chirality center .
2. Rotate the model so that the group with lowest priority (d) is
directed away from us.
3. Then trace the path from a to b to c.

• If direction is clockwise: R
• If direction is counterclockwise: S
How to find the priority
• Priority is first assigned on the basis of the atomic number of
the atom that is directly attached to the chirality center.
Continues….
• When a priority cannot be assigned on the basis of the atomic
number of the atoms that are directly attached to the chirality
center, then the next set of atoms in the unassigned groups is
examined.
• This process is continued until a decision can be made.
Continues….
• Groups containing double or triple bonds are assigned priorities
as if both atoms were duplicated or triplicated.
Activity : Give the labels to the chiral
centers of following molecules
S R S
S S R
Racemic mixture
• An equimolar mixture of two enantiomers is
called a racemic mixture (or racemate or
racemic form).
• A racemic mixture causes no net rotation of

plane-polarized light.
– enantiomers rotate the plane of plane-polarized
light equal amounts but in opposite directions.
Diastereomers
• Diastereomers are stereoisomers whose molecules are not

mirror images of each other.
• We can discuss two types of molecules which can show

diastereomerism
• Molecules having two chiral centers
• Molecules having double bonds
Molecules having two chiral centers
• A compound n number of chiral centers, the

total number of stereoisomers will not exceed
2n, where n is equal to the number of chiral
centers.
• Therefore maximum number of stereoisomers

for a molecule with two chiral centers is four.
Lets try to identify four isomers
• Eg: 2,3-dibromopentane
1 and 2 are non superimposable mirror
images of each other; thus 1
and 2 represent a pair of enantiomers.
Similarly 3 and 4 are non superimposable

mirror images of each other; thus 3
and 4 represent a pair of enantiomers.
1 and 3 are stereoisomers and they

are not mirror images of each other. They
are, therefore, diastereomers.
2 and 4 are stereoisomers and they

are not mirror images of each other. They
are, therefore, diastereomers.
1 (2S,3R) 2(2R,3S) 3(3R,3R) 4(2S,3S)
Situations where we can observe only
three
• Eg: 2,3-dibromobutane
A and B are nonsuperposable mirror images thus represent
a pair of enantiomers
C and D are superimposable it means C and D represent

identical orientations of the
same compound
A and C are stereoisomers and they are not mirror images

of each other. They are, therefore, diastereomers.
B and C are stereoisomers and they are not mirror images

of each other. They are, therefore, diastereomers.
A (R,R) B(S,S) C(R,S) D(S,R)
Compounds that contains two chiral centers and has an internal plane of
symmetry is called as meso compound.
Therefore the compound C { (2R,3S)-2,3-dibromobutane }is a
mesocompound
Meso compounds are achiral
Alkene diastereomers
• You are familiar with cis-trans isomers. They are

diastereomers to each other.
• If an alkene is trisubstituted or tetrasubstituted, the

terms cis and trans are ambiguous or do not apply
at all.
• There is a system called as (E )–(Z ) system which

can be applied to alkene diastereomers of all types.
How to use E-Z system
• After following the given three steps you can assign
the label.
1. Examine the two groups attached to one carbon atom of the
double bond and decide which has higher Cahn–Ingold–
Prelog priority.
2. Repeat that operation at the other carbon atom.
3. Compare the group of higher priority on one carbon atom

with the group of higher priority on the other carbon atom.
• If the two groups of higher priority are on the same side of the
double bond, the alkene is designated as (Z)
• If the two groups of higher priority are on opposite sides of the
double bond, the alkene is designated as (E)
Activity: give the E-Z labels
Z
E
E Z

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isomers

• Isomers are compounds that have the same molecular

• There are mainly two types of isomers

• These subdivisions can overlap.

• Position isomers are those which have the same

• Functional group isomers are those which have

• There are two types of stereoisomers

• What is a chiral molecule?

A molecule having a tetrahedral carbon atom

• Therefore that chiral

chiral molecule and its mirror

• As enantiomers are two different molecules, therefore

• R-S system or Cahn-Ingold-Prelog system is a part of the

• If we have a chiral center in the molecule, we have to put

3. Then trace the path from a to b to c.

• A racemic mixture causes no net rotation of

• Diastereomers are stereoisomers whose molecules are not

• We can discuss two types of molecules which can show

• A compound n number of chiral centers, the

• Therefore maximum number of stereoisomers

Similarly 3 and 4 are non superimposable

1 and 3 are stereoisomers and they

2 and 4 are stereoisomers and they

C and D are superimposable it means C and D represent

A and C are stereoisomers and they are not mirror images

B and C are stereoisomers and they are not mirror images

• You are familiar with cis-trans isomers. They are

• If an alkene is trisubstituted or tetrasubstituted, the

• There is a system called as (E )–(Z ) system which

2. Repeat that operation at the other carbon atom.

3. Compare the group of higher priority on one carbon atom

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