Topic 4 - The Ozone Story
Electronegativity
Electronegativity is the ability of an atom to attract the bonding electrons in a
covalent bond towards itself
Electronegativity increases along a period as atomic radius decreases
and charge density increases
Electronegativity decreases down a group as shielding increases and
atomic radius increases so charge density decreases
The greater the electronegativity value, the greater the bond polarity
Fluorine is the most electronegative atom with a value of 4 on the Pauling
scale
Polar molecules
Arise when there is a difference in polarity across a molecule due to the
arrangement of polar bonds and the geometry of the molecules.
CO2 has C=O polar bonds however due to the linear structure, the
dipoles cancel each other out
Polar molecules with permanent dipoles can align to form lattices
Induced dipoles form when electron orbitals are influenced by the
distributions of electrons on other particles.
Intermolecular forces
There are 3 types of intermolecular forces, differing in strength and location
Induced dipole bond (Van der Waals Forces)
Weakest type
Act as induced dipole between molecules
Varies on the Mr and shape of a molecule
o Larger Mr = stronger intermolecular forces
Act between organic alkane chains
o Longer chains increase forces
Branching of alkane chains weakens forces since they can pack less tightly
together
Group 7 elements have weak forces
o Increase down the group due to RAM increasing
Permanent dipoles
Act between molecules with polar bonds
Polar regions on adjacent molecules attract each other, holding molecules
together like a lattice structure
Hydrogen bonding
Only act between hydrogen and nitrogen, oxygen and fluorine
The lone pair of electrons on these atoms forms a bond with the hydrogen
atom from another molecule
Molecules with hydrogen bonds have very high mp and bp
Water has hydrogen bonds, hence its high boiling point
E = hv
Energy = Planck’s constant x frequency of light
(6.61x10-34)
C = fv
Speed of light (3x108) = wavelength x frequency
Nucleophilic substitution mechanism
Nucleophiles (electron donors) attack haloalkanes
Aqueous potassium hydroxide is used to produce alcohols
Potassium cyanide is used to produce nitriles
Ammonia is used to produce amines
Mechanism for producing an alcohol
The nucleophile (OH-) attacks the positive carbon and electrons are transferred
to chlorine
Mechanism for producing an amine
The intermediate has a positively charged nitrogen. Electrons are transferred to
the nitrogen by the loss of a hydrogen atom
Fission
Heterolytic fission:
Both shared electrons go to one atom when the bond breaks, this atom
gaining a negative charge. It is common when a bond is already polar
Homolytic fission:
One electron goes to each atom.
Radicals are commonly formed when the bond being broken is non-polar. The
amount of energy required to break the bond depends on the bond enthalpy of
the bond being broken.
Radicals
Alkanes react with halogens in the presence of UV light to produce haloalkanes
UV light breaks down halogen bonds (homolytic fission) to produce free radicals
Free radicals contain an unpaired electron
Freed radicals attack alkanes, causing initiation, propagation and termination
Initiation – halogen is broken down by UV light
Cl2 2Cl radicals
Propagation – hydrogen is replaced, and the Cl radical is reformed as a catalyst
Cl + CH4 CH3 radical + HCl
CH3 radical + Cl2 CH3Cl + Cl radical
Termination – two radicals join to end the chain reaction
CH3 radical + CH3 radical C2H6
CFCs and the ozone
CFCs produce halogen with UV radiation in the upper atmosphere
CFCs are chlorofluorocarbons
These radicals catalyse the breakdown of the ozone layer
Initiation: CF3Cl CF3 radical + Cl radical
Propagation: Cl radical + O3 ClO radical + O2
ClO radical + O 3 Cl radical + 2O2
The chlorine radical is regenerated in the second propagation step
Nitrogen oxide in the atmosphere
Initiation: NO2 NO + O
Propagation: NO + O3 NO2 + O2
NO2 + O NO + O2
Overall: O3 + O 2O2