Structure

Double
Bond
 Ethene

Dot and cross diagram

Ethene
Ethene
 Problems!
• Bond angle is 120°

• That is the bond angle for three bond

pairs

•Is the double bond a super

bond made of two bond pairs?
 Will this help?

We combine the four orbitals in These four hybrid orbitals are

the second shell to get four called sp orbitals. They repel to
identical electron charge clouds give the tetrahedral shape found
with four bond pairs
 Tetrahedral carbon atoms
• The four sp orbitals in
carbon allow four single
covalent bonds to form
109.5°

• The four identical charge

clouds repel each other
to give a bond angle of
109.5°

Remember, nitrogen and oxygen have

tetrahedral atoms too
Applying the hybrid model to

THE BONDING IN ETHENE

Does that mean ethene looks like this?

Overlapping orbitals

H H
C C
H H
Overlapping orbitals
 Problems
•Bond angle is 109.5°
•That is four bond pairs

•Is the double bond made from

two single bonds?
 So ethene doesn’t look like this!

unstable

H H
109.5° C C 109.5°

H H
Un-useable
This is not on the AS syllabus

SIGMA AND PI BONDS

Sigma (Single) bonds (simplified slightly)

Sigma σ

Sigma σ

Sigma σ
 sp Sigma σ

sp Sigma σ

Sigma (Single) bonds (simplified slightly)

Pi (double) bonds
Three bond pairs
give ethene the
expected 120°
bond angle around
each carbon.
The single
unbonded electron
on each carbon
relaxes into a p
orbital.
Pi (double) bonds
These p orbitals
overlap to form a
new type of bond;

A π ( pi ) bond
Pi (double) bonds
These p orbitals
overlap to form a
new type of bond;

A π ( pi ) bond
Pi bond diagrams
Pi bond diagrams
• This shows the
sigma bonds
formed by the
carbon and
hydrogen atoms
Pi bond diagrams
These p orbitals
should overlap to
form a new type of
bond;

A π ( pi ) bond
Pi bond diagrams
• Both together

• To show the sigma

bonds and the Pi
bond.
 Models
• I prefer this
model

• It shows the
shortness of the
C-C bond
• Which enables
the p orbitals to
overlap
An orbital view of the bonding in ethene
• Ethene is built from hydrogen atoms (1s1) and carbon
atoms (1s22s22px12py1).

• The carbon atom doesn't have enough unpaired

electrons to form the required number of bonds, so it
needs to promote one of the 2s2 pair into the empty
2pz orbital. This is exactly the same as happens
whenever carbon forms bonds - whatever else it ends
up joined to.
 Promotion of an electron

There is only a small energy gap between the 2s and 2p orbitals, and
an electron is promoted from the 2s to the empty 2p to give 4
unpaired electrons. The extra energy released when these electrons
are used for bonding more than compensates for the initial input.
The carbon atom is now said to be in an excited state.
 Hybridisation
When the carbon atoms hybridise their outer orbitals before forming
bonds, this time they only hybridise three of the orbitals rather than all
four. They use the 2s electron and two of the 2p electrons, but leave
the other 2p electron unchanged.
The new orbitals formed are called sp2 hybrids,
because they are made by an s orbital and two p
orbitals reorganising themselves. sp2 orbitals
look rather like sp3orbitals

The three sp2 hybrid orbitals arrange

themselves as far apart as possible - which is at
120° to each other in a plane. The remaining p
orbital is at right angles to them.
 The two carbon atoms and four
hydrogen atoms would look like this
before they joined together:

The various atomic orbitals which are pointing towards each

other now merge to give molecular orbitals, each containing a
bonding pair of electrons. These are sigma bonds - just like
those formed by end-to-end overlap of atomic orbitals in, say,
ethane.
This sideways overlap also creates a molecular orbital, but of a
different kind. In this one the electrons aren't held on the line
between the two nuclei, but above and below the plane of the
molecule. A bond formed in this way is called a pi bond.
Be clear about what a pi bond is. It is a region of space in
which you can find the two electrons which make up the
bond. Those two electrons can live anywhere within that
space.