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Molecular
Geometries
and Bonding
 Molecular
Geometries
and Bonding
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What is isomerism?
Isomers are molecules with the same molecular formula
(i.e. the same number and type of atoms) but in which the
atoms are arranged in a different way.

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 Structural isomers have different structural formulae.
Three types of structural isomerism are chain isomerism,
positional isomerism and functional group isomerism.

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Chain isomerism in alkanes
In chain isomers, the carbon chain is arranged differently.

hexane

2,3-dimethylbutane

3-methylpentane
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Positional isomerism
In positional isomers, the functional group is attached to
a different carbon atom.

1-chloropentane

2-chloropentane

3-chloropentane

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Positional isomerism in alkenes
Positional isomerism also exists in alkenes with four or more
carbon atoms.

hex-1-ene

hex-2-ene

hex-3-ene

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Functional group isomerism
Functional group isomers contain different functional groups

For example, both alcohols and ethers have the general

formula CnH2n+2O so they may be functional group isomers:

propanol (C3H8O) methoxyethane (C3H8O)

an alcohol an ether

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Functional group isomerism
Functional group isomers contain different functional groups

Alcohol and Ether R-OH & R-O-R CnH2n+2O

Carboxylic Acid and Ester R-COOH & R-COOR CnH2nO2
Alkene and Cycloalkane R2C=CR2 & Rings CnH2n
Aldehyde and Ketone RCHO & RCOR CnH2nO

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Structural isomers activity

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 Stereoisomers have the same structural formula, but
the 3D arrangement of atoms is different. Two types
are cis–trans isomerism and optical isomerism.

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Rotation around the C=C bond in alkenes
Molecules can rotate freely around single C-C covalent bonds,
but not around C=C double bonds.

is not the
same as

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Cis–trans isomerism
If an alkyl group or atom other than hydrogen is attached
to each carbon then the isomers can be named either
cis (‘on the same side’) or trans (‘on the opposite side’).

cis-but-2-ene trans-but-2-ene

cis-1,2-dichloroethene trans-1,2-dichloroethene
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Exercise

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Objects

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Objects

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Objects

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Optical isomerism
Another form of stereoisomerism is optical isomerism, in
which a molecule can exist as two isomers that are non-
superimposable, mirror images of each other, just like a left
hand and right hand.

optical isomers of the

amino acid alanine
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Stereoisomerism: true or false?

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What’s the keyword?

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Multiple-choice quiz

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