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Isomerism

The document discusses isomerism, including constitutional isomerism, stereoisomerism, and enantiomers. Constitutional isomerism includes chain, positional, and functional group isomers. Stereoisomers include cis-trans isomers and enantiomers. Enantiomers are non-superimposable mirror images that are often optically active.

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291 views30 pages

Isomerism

The document discusses isomerism, including constitutional isomerism, stereoisomerism, and enantiomers. Constitutional isomerism includes chain, positional, and functional group isomers. Stereoisomers include cis-trans isomers and enantiomers. Enantiomers are non-superimposable mirror images that are often optically active.

Uploaded by

NorsyazaEdmira
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Lecture 4:

12.4 Isomerism

Learning Outcomes:
At the end of the lesson the
students should be able to :
Define isomerism.
Explain constitutional isomerism.
chain isomers
positional isomers
functional group isomer

Isomerism

Structural/
Constitutional Isomerism

Chain
Isomerism

Positional
Isomerism

Stereoisomerism

Functional Group Diastreomer


Isomerism
cis-trans
isomerism

Enantiomer

other
diastereomers

Isomerism
is the existence of different
compounds with the same molecular
formula but different structural
formulae.

Different structural formula that have


the same molecular formula are called
isomer

1) Constitutional isomers
(Structural isomers)
are isomers with the same
molecular formula but differ in
the order of attachment of
atoms.
2) Stereoisomers
are isomers with the same
molecular formula but different
arrangement of atoms in space

Constitutional isomerism
Isomerism resulting from different
order of attachment of atoms.
Three types
a) Chain/skeletal isomerism
b) Positional isomerism
c) Functional group isomerism

a) Chain/skeletal isomerism
The isomers differ in the carbon skeleton
(different carbon chain).
They possess the same functional group and
belong to the same homologous series.

Example:

CH3

C5H12
CH3CH2CH2CH2CH3

CH3CCH3

Pentane

CH3CHCH2CH3

CH3

2,2-dimethylprop

CH3 2-methylbutane

2)Positional isomerism
These isomers have a substituent group/
functional group in different positions.

Examples

C3H7Cl

CH3CH2CH2Cl
1-chloropropane

CH3CHCH3
Cl
2-chloropropane

C 4 H8

CH2=CHCH2CH3
1-butene

CH3CH=CHCH3
2-butene

C8H10
CH3

CH3

CH3
CH3

CH3

1,2-dimethylbenzene 1,3-dimethylbenzene

CH3
1,4-dimethylbenzene

C6H13N
NH2
CH3

CH3
H2N

CH3
CH2NH2

NH2

3)Functional group isomerism


These isomers have different functional
groups and belong to different
homologous series with the same general
formula.
Different classes of compounds that
exhibit functional group isomerism :General formula Classes of
compounds
CnH2n+2O ; n > 1
alcohol and ether

CnH2nO ; n 3

aldehyde and ketone

CnH2nO2 ; n 2

carboxylic acid and


ester
alkene and

CnH2n ; n 3

Examples:
CH3CH2OH
C 2 H6 O
ethanol

dimethyl ether

C 3 H6 O

CH3CCH3

CH3CH2CH

O
propanone

O
propanal

C 3 H6 O 2

CH3CH2COH
O

propanoic acid

CH3OCH3

CH3COCH3
O
methyl ethanoate

Exercise 1:
Identify the relationship between the following pairs of compounds.

Position

Chain

Identical pairs

Functional group

Position

Exercise:
1. State how many are isomers with the following
molecular formulae, identify the type of isomerism
and draw the structural formula of the isomers.
a) C5H10
b) C5H10O2
c) CH3CH=C(Cl)CH3
d) C4H6Cl2
e) CH3CH2CH(OH)CH(Br)CH2CH3

Lecture 5
12.4 Isomerism
Learning Outcomes:
At the end of the lesson the students
should be able to :
Define stereoisomerism.
Describe cis-trans isomerism due to
restricted rotation about C=C bond
and CC bond in cyclic compounds
Identify cis-trans isomerism of a
given structural formula.

Stereoisomerism / Optical
Isomerism
Isomerism that resulting from
different spatial arrangement of
atoms in molecules.
Two subdivisions of stereoisomers:
i) Diastereomers (non-mirror
image)
ii) Enantiomers (mirror image)

Diastereomer
Cis-Trans Isomerism
The requirements for geometric
isomerism :
i) Restricted rotation about a
C=C,double
bond in alkenes, or a CC single bond
in cyclic compounds.
ii) Each carbon atom of a site of
restricted rotation has two different
groups
attached to it.

Examples

H
C

H3C

CH3
H

trans-2-butene
H

CH3 CH3

H3C
C

CH3

H
H
cis-2-butene

CH3 H
H

CH3

cis-1,2-dimethylcyclohexane
trans-1,2-dimethylcyclohexane

If one of the doubly bonded


carbons has 2 identical groups,
geometric isomerism is not
possible.
Example

H3C

C
H3C

CH3
H

No cis trans isomer

CH3CH2

CH3

C=C
H 3C

C=C
H

Cl

CH3

2-methyl-2-butene

1-chloro-2-methylpropene

No cis trans isomer

Lecture 6
12.4 Isomerism
Learning Outcomes:
At the end of the lesson the students should
be able to :
Identify cis-trans isomerism of a given
structural formula.
Define chirality centre and enantiomers.
Identify chirality centre in a molecule.
Explain optical activity of a compound.
Draw a pair of enantiomers using 3-dimensional
formula.
Define racemate.
State the applications of chiral compounds in
daily life.

Enantiom
Optical Isomerism
er

Optically active compounds


have the ability to rotate planepolarized light to the right
(dextrorotary) and to the left
(levorotary)
The angle of rotation can be
measured with an instrument
called polarimeter.

Unpolarized light

Dextrorotatory (+)

Polarized light

Levorotatory (-)

The requirements for optical


isomerism :i)
Molecule contains a chiral carbon or
chirality centre or stereogenic centre (a
sp3-hybridized carbon atom with 4
different groups attached to it)
P

C*

PQRS
*designates chiral centre

R
ii)

Molecule is not superimposable with


its mirror image.

Enantiome
rs that are not
a pair of mirror-image
superimposable.
*
CH3CHCH2CH3
Example:i)
2-butanol ,
OH

H3C

CH2CH3

CH2CH3

C*

OH

Enantiomers

CH3
OH

ii) 2-hydroxypropanoic acid,


*

CH3CHCOOH
OH

COOH

COOH

C*

OH
CH3

HO

H
CH3

Enantiomers

- A compound with n chiral centers can


have a maximum of 2n stereoisomers.
- If a molecule contains two or more chiral
centers, diastereomers may exist.

Diastereomers are stereoisomers that


are not mirror images of each other.

Racemate Mixture
A racemic mixture or racemate is
an equimolar mixture of enantiomers
which is optically inactive because
the two components rotate planepolarized light equally (same degree
of rotation) but in opposite directions.
Hence it does not give a net rotation
of plane-polarized light.

Applications of chiral
compounds in daily life.
() Dopa is used for treatment
of Parkinsons disease but
(+) dopa is toxic to human.
(S)-Ibuprofen the popular
analgesic(the active
ingredient in motrin, advil,
and many other nonaspirin
analgesics)

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