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Free Radical Substitution Initiation

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Organic Mechanism 3
Reaction of Chlorine with Methane
TY 2003
Free Radical Substitution
Overall equation
CH4 + Cl2
CH3Cl + HCl
1. Initiation – produces free radicals
2. Propagation – free radicals react
with molecules to produce more free
radicals
3. Termination – free radicals react to
produce molecules
TY 2003
First Step - Initiation
Initiation involves the production of free radicals
Cl пЂ­ Cl
пѓ Cl п‚·
Cl п‚·
• UV light is required for this step, it
provides the energy to split the Cl-Cl bond
• Homolytic Fission occurs
• Free Radicals are formed
TY 2003
Initiation – Key Terms
• Homolytic Fission
a covalent bond breaks so that one electron
from the shared pair goes to each atom
• Free Radical
any species with an unpaired electron
TY 2003
Cl2
2Cl п‚·
TY 2003
Second Step - Propagation
Propagation involves the reaction of free radicals
with molecules to produce free radicals
• No light is required for this stage
• All bonds split homolytically
• Every reaction produces a free radical
TY 2003
Molecule
H
H
Cl п‚· + H пЂ­ C пЂ­ H
Cl пЂ­ H +
пѓ H
п‚·CпЂ­H
H
Free Radical
H
H пЂ­ C п‚· + Cl пЂ­ Cl
H
TY 2003
H
пѓ H пЂ­ C пЂ­ Cl + Cl п‚·
H
Final Step - Termination
Termination involves the reaction of free radicals
to produce a molecule
• This final step can involve any two free radicals
• No light is required for this step
• Chloromethane is produced but many other
products are also formed because there are lots
of different free radicals which can combine
TY 2003
H
Cl п‚· +
п‚·CпЂ­H
H
пѓ H
Cl п‚· + Cl п‚·
H
п‚·CпЂ­H
H
TY 2003
H
пѓ H
п‚· CпЂ­H
H
Cl пЂ­ C пЂ­ H
Cl пЂ­ Cl
H
пѓ H
HпЂ­CпЂ­CпЂ­H
H H
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