Haloalkanes can be made from alkanes through free radical substitution, or from alkenes through electrophilic addition.
Free radical substitution occurs in three steps:
initiation
propagation
termination
Initiation phase:
Must take place with UV light as it provides energy to break Cl-Cl bonds.
Initiation Phase
The Cl-Cl bonds break to form two chlorine radicals that both contain one free unpaired electron in their outer shells.
Initiation Phase Equation
Cl2 --> 2Cl•
UV
Propagation Phase Part 1
A chlorine radical reacts with a methane, and bonds with a hydrogen, forming hydrochloric acid and a radical methyl that has an unpaired free electron on the carbon.
Propagation Phase Equations
i) Cl• + CH4 --> HCl + •CH3
ii) •CH3 + Cl2 --> CH3Cl + Cl•
Propagation Phase Part 2
The radical methyl bonds with a Cl from a CL2, forming chloromethane and a radical chlorine.
Termination
Any two radicals react to form a stable, neutral molecule.