TOPIC 18: Teaching plan 18A.

1 Benzene: a molecule with two models

Student Book links Specification links Links to prior learning Suggested teaching order
● 18A.1 ● 18.1 ● IUPAC nomenclature of 1. The structure of benzene, including historical
● 18.2 organic compounds theories through to modern theories.

● 18.3 ● Alkanes and alkenes 2. Evidence for the current model of benzene’s
● Standard enthalpies structure, including bond length and enthalpy
changes of hydrogenation.
● Electrophilic addition of
alkenes 3. The resistance of benzene to bromination
compared to alkenes.
Learning objectives
Students should be able to:
● use thermochemical, X-ray diffraction, and infrared data as evidence for the structure and
stability of the benzene ring
● understand that the delocalised model for the structure of benzene involves overlap of p-
orbitals to form π-bonds
● understand why benzene is resistant to bromination, compared with alkenes, in terms of
delocalisation of π-bonds in benzene compared to the localised electron density of the π-bond
in alkenes.
Key terms Practical skills
● Aromatic There are no new practical skills in this section.
Maths skills Digital learning ideas
There are no new maths skills in this section. ● Research organic nomenclature using the IUPAC
Blue Book.
● Research online data for bond lengths and
enthalpies of hydrogenation.
Pre-unit homework suggestions
● Revise the nomenclature of organic molecules.
● Look up the words aliphatic, aromatic and arene.

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Suggested starter activities Equipment Teacher notes
1. In groups, students use a molecular modelling kit to Molecular modelling kit: 6 carbon Students will almost certainly come up with alternating
suggest a structure for benzene. atoms, 6 hydrogens, 18 bonds double and single bonds in a ring but there are other
possibilities.

2. Students try to name as many arenes as they can in one Cards Prepare a selection of cards with structures of arenes.
minute. This activity could be extended as students become
more confident, instead using cards with the compound
name so that students have to draw the corresponding
structure.
3. Students carry out a risk assessment regarding the use
of benzene in the laboratory.
Suggested main activities Equipment Teacher notes
1. Students prepare a presentation on the history of Students should consider the Kekulé and the modern
benzene. delocalised models.
2. Lead a discussion on the evidence for the modern Student Book, mini whiteboard Students look up the bond lengths of a C=C double
delocalised structure. bond and C–C single bond and compare them to the
length of C…C bonds found in benzene.
Students can do the same with standard enthalpy of
hydrogenation data of an alkene versus benzene.
Students should practise drawing the enthalpy level
diagram on their mini whiteboards.
3. Students discuss the lack of reactivity of benzene, Orbital molecular models of A molecular model of benzene should be used to
particularly in electrophilic addition reactions, such as benzene and ethene explain the overlap of p-orbitals giving the delocalised
bromination. electron structure of the molecule. This model can be
used to explain the lack of mobility of these delocalised
electrons compared to the π-bond in alkenes.
Suggested plenary activities Equipment Teacher notes
1. In pairs, students take it in turns to give descriptive clues The first clues should be difficult and become
for a key term so that their partner can correctly guess progressively easier.
what it is. The aim is to identify the key term with as few
clues as possible.

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2. Students debate which is the most likely structure of
benzene based on the evidence for the different
theories.
3. Students answer the questions at the end of Section Student Book
18A.1 in the Student Book.
Homework suggestions
● Answer past paper questions relating to the structure of benzene.
Wider reading
● Research the uses of benzene and its derivatives.
Support ideas
● Students should know the skeletal structure of benzene.
Extension ideas
● Research the term ‘resonance hybrid structure’.
Potential misconceptions
● Benzene does have C=C bonds.
● Students often forget the hydrogen atom joined to each carbon atom.
Links to future learning
● Electrophilic substitution mechanisms (Section 18A.3)
● Phenol (Section 18A.4)
Notes

© Pearson Education Ltd 2019. Copying permitted for purchasing institution only. This material is not copyright free. This document may have been altered from the original.
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