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Chapter 10: Radicals
BY: DANIEL EISENSTEIN
Some things about radicals
 SP^2
 Trigonal planar
Radical stability
Radical Mechs
 Homolytic Cleavage
 Addition to a pi bond
 Hydrogen Abstraction
 Halogen Abstraction
 Elimination
 Coupling
Radical Mechs
But WAIT THERE IS MORE
 Homolytic cleavage=initiation
 Addition to pi bond, H abstraction, X abstraction and
elimination= propagation
 Coupling=termination
 Coupling and cleavage= opposites
 Hydrogen and halogen abstraction=opposites
3 steps
 Initiation
 Propagation
 Termination
Radical Chlorination
 Homolytic cleavage
 Hydrogen abstraction
 Halogen Abstraction
 Coupling (3 ways to do it)
Radical initiators and inhibitors
 Initiators: heat, light, hydrogen peroxide
 Inhibitors: oxygen
 Radicals are actually really cool and important in
biology
 Just look at Superoxide dismutase
REALLY IMPORTANT ENZYME
Halogenation of Alkane
 Bromination is more selective than
chlorination
Bromination on an alkene
 Say we have propene
 We can do what we did in chapter 8
 We can do allylic bromination
 We can do both or choose one depending on the
reagents chosen
Radical Hydrohalogenation
Radical Polymerization
Mech
Wiley chapter 10

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Wiley chapter 10