THE CHEMISTRY

OF BENZENE
A guide for A level students

KNOCKHARDY PUBLISHING
2008
SPECIFICATIONS
 CONTENTS
• Prior knowledge
• Structure of benzene
• Delocalisation
• RESONANCE HYBRID
 Before you start it would be helpful to…

• know the arrangement of bonds around carbon atoms

(Hybridization)
 HYBRIDISATION OF ORBITALS - REVISION

2p
The electronic configuration of a 2
carbon atom is 1s22s22p2 2s

1 1s
 HYBRIDISATION OF ORBITALS - REVISION

2p
The electronic configuration of a 2
carbon atom is 1s22s22p2 2s

1 1s

If you provide a bit of energy you 2p

2
can promote (lift) one of the s 2s
electrons into a p orbital. The
configuration is now 1s22s12p3
1 1s

The process is favourable because of the arrangement of

electrons; four unpaired and with less repulsion is more stable
 HYBRIDISATION OF ORBITALS - REVISION

The four orbitals (an s and three p’s) combine or HYBRIDISE

to give four new orbitals. All four orbitals are equivalent.

2s22p2 2s12p3 4 x sp3

HYBRIDISE

sp3
HYBRIDISATION
 HYBRIDISATION OF ORBITALS - REVISION

Alternatively, only three orbitals (an s and two p’s) combine or

HYBRIDISE to give three new orbitals. All three orbitals are
equivalent. The remaining 2p orbital is unchanged.

2s22p2 2s12p3 3 x sp2 2p

HYBRIDISE

sp2
HYBRIDISATION
 STRUCTURE OF ALKENES - REVISION

In ALKANES, the four sp3 orbitals

repel each other into a tetrahedral
arrangement.

In ALKENES, the three

sp2 orbitals repel each
other into a planar
arrangement and the
2p orbital lies at right
angles to them
 STRUCTURE OF ALKENES - REVISION

Covalent bonds are formed An sp2 orbital from each carbon

by overlap of orbitals. overlaps to form a single C-C bond.

The resulting bond is called

a SIGMA (δ) bond.
 STRUCTURE OF ALKENES - REVISION

The two 2p orbitals also overlap. This forms a second bond; it

is known as a PI (π) bond.

For maximum overlap and hence the strongest bond, the 2p

orbitals are in line.

This gives rise to the planar arrangement around C=C bonds.

 ORBITAL OVERLAP IN ETHENE - REVIEW

two sp2 orbitals overlap to form a sigma two 2p orbitals overlap to form a pi
bond between the two carbon atoms bond between the two carbon atoms

s orbitals in hydrogen overlap with the the resulting shape is planar

sp2 orbitals in carbon to form C-H bonds with bond angles of 120º
 STRUCTURE OF BENZENE

Primary analysis revealed benzene had...

an empirical formula of CH and

a molecular mass of 78 and

a molecular formula of C6H6

 STRUCTURE OF BENZENE

Primary analysis revealed benzene had...

an empirical formula of CH and

a molecular mass of 78
a molecular formula of C6H6

Kekulé suggested that benzene was...

PLANAR
CYCLIC and
HAD ALTERNATING DOUBLE AND SINGLE BONDS
 STRUCTURE OF BENZENE

It was suggested that the structure oscillated

between the two forms but was represented by neither of
them. It was a RESONANCE HYBRID.
 STRUCTURE OF BENZENE - DELOCALISATION
The theory suggested that instead of three localised (in one position) double bonds,
the six p (p) electrons making up those bonds were delocalised (not in any one
particular position) around the ring by overlapping the p orbitals. There would be no
double bonds and all bond lengths would be equal. It also gave a planar structure.

6 single bonds
 STRUCTURE OF BENZENE - DELOCALISATION
The theory suggested that instead of three localised (in one position) double bonds,
the six p (p) electrons making up those bonds were delocalised (not in any one
particular position) around the ring by overlapping the p orbitals. There would be no
double bonds and all bond lengths would be equal. It also gave a planar structure.

6 single bonds one way to overlap

adjacent p orbitals
 STRUCTURE OF BENZENE - DELOCALISATION
The theory suggested that instead of three localised (in one position) double bonds,
the six p (p) electrons making up those bonds were delocalised (not in any one
particular position) around the ring by overlapping the p orbitals. There would be no
double bonds and all bond lengths would be equal. It also gave a planar structure.

6 single bonds one way to overlap another

adjacent p orbitals possibility
 STRUCTURE OF BENZENE - DELOCALISATION
The theory suggested that instead of three localised (in one position) double bonds,
the six p (p) electrons making up those bonds were delocalised (not in any one
particular position) around the ring by overlapping the p orbitals. There would be no
double bonds and all bond lengths would be equal. It also gave a planar structure.

6 single bonds one way to overlap another delocalised pi

adjacent p orbitals possibility orbital system
 STRUCTURE OF BENZENE - DELOCALISATION
The theory suggested that instead of three localised (in one position) double bonds,
the six p (p) electrons making up those bonds were delocalised (not in any one
particular position) around the ring by overlapping the p orbitals. There would be no
double bonds and all bond lengths would be equal. It also gave a planar structure.

6 single bonds one way to overlap another delocalised pi

adjacent p orbitals possibility orbital system
STRUCTURE OF BENZENE
STRUCTURE OF BENZENE
ANIMATION
THE CHEMISTRY
OF ARENES
THE END

© 2009 KNOCKHARDY PUBLISHING