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reactivity_3.3

The document discusses the concept of radicals in chemistry, highlighting their formation through homolytic fission, particularly in halogens under UV light or heat. It outlines the process of radical substitution reactions involving alkanes, detailing the initiation, propagation, and termination steps with relevant equations. Additionally, it emphasizes the reactivity of radicals and their role in producing a mixture of products during these reactions.

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28 views

reactivity_3.3

The document discusses the concept of radicals in chemistry, highlighting their formation through homolytic fission, particularly in halogens under UV light or heat. It outlines the process of radical substitution reactions involving alkanes, detailing the initiation, propagation, and termination steps with relevant equations. Additionally, it emphasizes the reactivity of radicals and their role in producing a mixture of products during these reactions.

Uploaded by

Jooobug준벅님
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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Reactivity 3.

3
IB CHEMISTRY SL
Reactivity 3.3.1 and 3.3.2
Understandings:
• A radical is a chemical entity that has an unpaired electron. Radicals are highly
reactive (3.3.1).
• Radicals are produced by homolytic fission, e.g. of halogens, in the presence of
ultraviolet (UV) light or heat (3.3.2).
Learning outcomes:
• Identify and represent radicals (3.3.1).
• Explain, including with equations, the homolytic fission of halogens, known as the
initiation step in a chain reaction (3.3.2).
Additional notes:
• The use of a single-barbed arrow (fish hook) to show the movement of a single
electron should be covered.
Linking questions:
• Structure 2.1 How is it possible for a radical to be an atom, a molecule, a cation or
an anion? Consider examples of each type.
• Reactivity 1.2 Why do chlorofluorocarbons (CFCs) in the atmosphere break down
to release chlorine radicals but typically not fluorine radicals?
• Structure 2.2 What is the reverse process of homolytic fission?
• Structure 2.2 Chlorine radicals released from CFCs are able to break down ozone,
O3, but not oxygen, O2, in the stratosphere. What does this suggest about the
relative strengths of bonds in the two allotropes?

REACTIVITY 3.3 WWW.MSJCHEM.COM 1


Homolytic bond fission
• In homolytic bond fission, (also known as homolytic bond cleavage), a covalent
bond between two atoms in a molecule breaks with each atom taking one electron
from the bond.
• The breaking of the bond requires energy in the form of UV radiation or heat.
• Homolytic fission results in the formation of radicals (or free radicals) which are
highly reactive species with unpaired electrons.
• For example, the covalent bond between two atoms of X breaks with each atom
taking one electron from the bond.

• The single-barbed arrows (known as fish hooks) show the movement of a single
electron.
• The radicals formed are represented with a single dot such as X⦁.

Homolytic fission of the halogens


• The bond between the two atoms in chlorine, Cl2, can undergo homolytic fission in
the presence of ultraviolet (UV) radiation.

• The products of the fission are two chlorine radicals, represented as Cl⦁.

Cl2 → 2Cl⦁ or Cl2 → Cl⦁ + Cl⦁


• The formation of radicals is the first step, known as the initiation step, in the free-
radical substitution reactions of the alkanes.
• The bond between the two atoms in Bromine, Br2, can also undergo homolytic
fission in the presence of UV radiation.

• The products of the fission are two bromine radicals, represented as Br⦁.

Br2 → 2Br⦁ or Br2 → Br⦁ + Br⦁

Exercise: Outline the type of bond fission taking place in the reaction below.

REACTIVITY 3.3 WWW.MSJCHEM.COM 2


Reactivity 3.3.3
Understandings:
• Radicals take part in substitution reactions with alkanes, producing a mixture of
products.
Learning outcomes:
• Explain, using equations, the propagation and termination steps in the reactions
between alkanes and halogens.
Additional notes:
• Reference should be made to the stability of alkanes due to the strengths of the
C–C and C–H bonds and their essentially non-polar nature.
Linking questions:
• Reactivity 2.2 Why are alkanes described as kinetically stable but
thermodynamically unstable?

Radical substitution reactions of the alkanes


• Alkanes undergo radical substitution reactions which take place in three stages:
initiation, propagation and termination.
• Example – methane and chlorine react as follows in the presence of UV light as
follows.
CH4(g) + Cl2(g) → CH3Cl(g) + HCl(g)
Initiation
• The bond between the chlorine atoms undergoes homolytic fission in the
presence of UV light.
• Each chlorine atom takes one electron from the single bond resulting in the
production of reactive chlorine radicals with unpaired electrons.

Cl2 → 2Cl⦁
Propagation
• The first propagation step shows methane reacting with a chlorine radical to
produce a methyl radical and hydrogen chloride.
• The second step shows the methyl radical reacting with a chlorine molecule to
produce chloromethane and a chlorine radical.

CH4 + Cl⦁ → ⦁CH3 + HCl

⦁CH3 + Cl2 → CH3Cl + Cl⦁


• Two more propagation steps are shown below.

CH3Cl + Cl⦁ → ⦁CH2Cl + HCl

⦁CH2Cl + Cl2 → CH2Cl2 + Cl⦁


REACTIVITY 3.3 WWW.MSJCHEM.COM 3
Termination
• In the termination step, radicals pair up to form molecules.

Cl⦁ + Cl⦁ → Cl2

⦁CH3 + ⦁CH3 → C2H6

⦁CH3 + Cl⦁ → CH3Cl

Exercise: Ethane, C2H6, reacts with bromine to form bromoethane, C2H5Br, in a radical
substitution reaction. Write initiation, propagation and termination steps for the reaction.

REACTIVITY 3.3 WWW.MSJCHEM.COM 4

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