HYDROCARBON : ALKENES

Nomenclature Of Alkenes And Cycloalkenes

1. Write the IUPAC names for the following alkenes.
(a)

(b)

(c)

(d)

(e)

(f)

2.. Draw the structural formulae for these alkenes.

(a) 4-Methylpent-2-ene

(b) 2-Ethyl-3-methylpent-l-ene

(c) 3,3-Dimethylcyclohexene

Name these alkenes according to the IUPAC nomenclature

(a)
(b)

(c)

(d)

THE STRUCTURE OF ALKENES

A carbon-carbon double bond (C=C) consists of one sigma () bond
and one pi () bond.
(a) Using the hybridisation theory, each carbon of the double bond
uses its three sp2 hybrid orbitals to form bonds to three atoms. The
three sp2 hybrid orbitals lie in a plane at angles of 120 to one another

The unhybridised 2p atomic orbital on each carbon lies perpendicular

to the plane. When the 2p orbitals of adjacent carbon atoms are
parallel to each other, they overlap sideways to form the bond of
the carbon-carbon double bond, one above and one below the plane of
the molecule
The and the bonds are stronger than the single bond that links
carbon atoms in alkanes.
Hence, the carbon-carbon double bond (C=C) in alkenes is stronger
and shorter than the carbon -carbon single bond (C-C) in alkanes.

THE EXISTENCE OF CIS-TRANS ISOMERISM

(GEOMETRICAL ISOMERISM)
Cis-trans isomers have the same molecular formula and the same order of attachment of atoms but differ in
arrangement of their atoms in space.
The restriction to rotation about a carbon-carbon double bond due to the presence of the bonds which lie above
and below the plane of the molecule gives rise to cis-trans isomerism.
An alkene shows cis-trans isomerism if each carbon atom of the double bond has two different groups attached to it.

The two methyl groups are on one side of the double

bond and the two hydrogen atoms are on the other
side
Cis-isomers are polar molecules.

The two methyl groups are on the opposite side of the

double bond.
Trans-isomer is more stable than the cis-isomer because
the two larger methyl groups are on the opposite side of
the double bond, hence, there is less strain on the
molecule.

These two compounds cannot be converted into one another at room temperature because of the restricted
rotation about the double bond; they are different compounds with different physical properties. In some
instances, they may differ in their chemical reactions.

Note that molecules which show geometrical isomerism always have two specific structural features:
- there is a carbon-carbon double bond
- both the carbon atoms are attached to two different groups.
Geometrical isomers should always be drawn using crab notation. Crab notation shows the C=C bond as a planar
centre with the 4 groups shown as follows:

Using crab notation, it is easy to predict whether geometrical isomerism will exist in molecules.
Ethene

C
Propene

CH3

C
But-1-ene

C 2H 5

CH3

H
C

CH3

CH3

C
H

H
C

CH2CH2CH3
H

H
C

CH3

CH3

No geometrical isomerism

C
H

C2 H5

CH3

C
CH3

Geometrical isomerism

C2H5

2-methylbut-2-ene

No geometrical isomerism

2-methylbut-1-ene

No geometrical isomerism

H
C

Pent-2-ene

Geometrical isomerism

CH3

Pent-1-ene

No geometrical isomerism

2-methylpropene

No geometrical isomerism

C
But-2-ene

No geometrical isomerism

C
CH3

No geometrical isomerism

3-methylbut-1-ene

H
C
H

No geometrical isomerism

C
CH(CH3)2

Name each compound below and show the configuration about each double bond using the cis-trans
system
(a)

The chain contains six carbon atoms and is numbered from the end that
gives the lowest number to the first carbon atom of the double bond. Its
name is trans-hex-3-ene.
(b)

The chain contains seven carbon atoms and is numbered from the end
that gives the lowest number to the first carbon of the double bond. Its
name is cis-hept-3-ene.

(c)

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