Guiding question: What

determines the covalent nature

Structure 2.2 and properties of a compound?

The covalent model

1
AHL content

2
Learning Objectives

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 Part A
Resonance structures

4
 1. Draw the Lewis formula for the nitrate ion, NO3- .
2. How many identical structures can you draw by moving the position of a
double bond. 5
What does the data tell us?

Bond length
Bond
(10-12 m)

N-O 136

All the nitrogen-oxygen bonds in the nitrate ion are

N=O 114
found to be of equal length at 124 x 10-12 m.

The sharing of electrons across multiple bonding positions is known as delocalization.

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Drawing a resonance hybrid

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Quick check

Bond
1. Draw the resonance structures of Bond
Bond length
enthalpy
(10-12 m)
ozone, O3. (kJ mol-1)
2. Use the data to predict an
approximate bond length and O-O 148 144
bond strength (enthalpy) for the
oxygen-oxygen bonds.
3. Draw a resonance hybrid for O=O 121 498

ozone.

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Practice questions

1. Identify which of the following species have resonance structures:

CO CO32- CO2 HCOO-
2. Draw the resonance structures of the nitrite ion, NO2- and predict the
approximate bond length and bond strength of the nitrogen-oxygen bonds
using section 10 and 11 in the data booklet.

3. Explain why the oxygen-oxygen bond in O2 requires light of a shorter

wavelength to dissociate (break) than O3.
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 Part B
Benzene

10
Draw 3 possible structures for a molecule with 6 carbons and 6 hydrogens.

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Benzene: August Kekulé’s 1865 suggestion for C6H6

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Benzene: Resonance structures and resonance hybrid

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Benzene: More commonly drawn as skeletal formulas

14
Benzene: Physical evidence for delocalization

Bond length Bond enthalpy

Bond
(10-12 m) (kJ mol-1)

C-C 154 346

C=C 134 614

carbon-carbon
140 507
in benzene

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Benzene: Chemical evidence for
delocalization

Approximate enthalpy changes of

hydrogenation (ΔHhydrogenation) →

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Benzene: Chemical evidence for delocalization

17
Benzene: Chemical evidence for the 6 carbon ring

Only 3 possible structures can be formed when 2 bromines replace 2 hydrogens

on the benzene ring.
Draw each of them.

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Practice questions

1. Explain, with reference to bond

lengths, which of these structures is the
most accurate representation of
benzene.

2. Describe 2 pieces of chemical evidence that support the presence of a

delocalised ring of electrons in benzene.
3. Draw the 3 possible isomers of dichlorobenzene.

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