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Cl2 + heat
statistically favored product
tertiary reactivity
5.0
secondary reactivity
3.8
primary reactivity
1.0
Br2 + heat
most substituted/stable H replaced
HBr + peroxides
anti-markovnikov bromination of alkene
HCl + peroxides
markovnikov addition to alkene
NBS + peroxides + heat
allylic/benzylic bromination with resonance
initiation
1 neutral becomes 2 radicals
propagation
1 neutral + 1 radical
termination
2 radicals become 1 neutral