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AN OVERVIEW OF BENZENE

This lesson covers:

What Benzene is
How we represent it
Two models for Benzene: Kekule’s model and the delocalised model

What is Benzene?

First identified in residue oil from gas lighting and isolated by Micheal Faraday in 1825,
benzene has gone on to be one of the most produced organic chemicals industrially, with many
major commodity chemicals polymers derived from benzene.

Carousel Slide 1:

text: Benzene comes in the form of a colourless liquid with a distinct sweet odour (it is not
recommended to sniff benzene). Its physical properties include it being highly volatile at room
temperature and standard pressure, meaning it evaporates with ease, as well as being highly
flammable.

Slide 2:
text: Above is the skeletal structure of benzene you may typically see in textbooks, as well as
in organic reaction pathways. Note that it contains 6 hydrogens, one bonded to each carbon,
that aren’t displayed here. Its chemical formula is simply C6H6.

Slide 3

text: Before the advent of sophisticated spectroscopic techniques that could determine its
shape accurately, several theories of benzene’s structure were proposed. There was very little
evidence to accurately say which structure was correct.

Slide 4:
img: Two pictures of benzene’s bonds interchanging (with arrows to show movement of
electrons)
text: Kekule proposed that benzene had 3 single and 3 double carbon bonds that were
interchanging instead of staying stationary.Kekule’s symmetrical ring structure agreed with
experimental data.

Missing Word Q:
Benzene is a colourless liquid at room temperature and is flammable. Its structure consists of
three single and three double carbon bonds.
 The two models of benzene

Kekule’s model of benzene explained some chemical phenomena, however there appeared
evidence against the alternating single and double carbon bond model.

Bond length
img: Comparative skeleton diagrams for single and double bond lengths.
text: If Kekule was correct, there should be two bond lengths in benzene: one for a single bond
(0.153 nm - nanometer) and one for a double bond (0.134 nm). A spectroscopic technique
called X-ray diffraction showed benzene’s bond lengths to all be the same length: 0.139 nm.
This means that there must be a new kind of bond within benzene, since it matches neither the
single or double bond length.

Reactivity of benzene
img: Images to show colour change of bromine from alkene addition.
text: If benzene were to contain alkene bonds, it should decolourise bromine upon addition.
However, no such change occurs. From this we can infer that benzene does not undergo
electrophilic addition reactions.

Hydrogenation enthalpies
img:

Text: Kekule’s model of three present double bonds doesn’t match experiment, with the
enthalpy change from its hydrogenation (-120 kJmol-1) not matching it in theory (-360
kJmol-1). From this we can infer that benzene is more stable than if it had three double bonds
within it.
Multiple choice:
What is the bond length in benzene?
0.153 nm
0.139 nm
0.134 nm

Single Answer Q:

Which kind of organic reaction mechanisms was benzene proven to not undergo?
Electrophilic addition

The delocalised model of benzene

From these three main pieces of experimental evidence, the delocalised structure model of
benzene was proposed:

This model accounts for the uniform bond lengths, its thermodynamic stability and its refusal
to undergo electrophilic addition reactions.

Main features of the delocalised model

Each carbon within benzene has one electron orbital which isn’t being used to chemically bond
(e.g. C-H or C-C). This p-orbital is situated at a right angle to the carbon atom.
Each carbon’s p-electron orbitals overlap on a flat plane to overlap. Each p-electron can now
‘delocalise’ from its respective carbon atom.

This creates a pi-system that spreads round the circle of carbon atoms.

Single Answer Q:

Which type of carbon’s electrons contribute to the delocalised system?

p-electrons

Missing Word Q:
The p electrons and their orbitals overlap and create a pi-system in benzene. This makes the
molecule stable and gives it uniform bond length between carbons.