Free Radical Substitution
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Table of Bond Disassociation Energies

  R-H H-F F-F C-F   Initial Propagation I Propagation II
methane 104 136 38 109 methyl fluoride 0 -32 -103
primary 98 136 38 107 primary fluoride 0 -38 -107
secondary 95 136 38 106 secondary fluoride 0 -41 -109
tertiary 91 136 38 106 tertiary fluoride 0 -45 -113
    H-Cl Cl-Cl C-Cl        
methane 104 103 58 84 methyl chloride 0 1 -25
primary 98 103 58 81 primary chloride 0 -5 -28
secondary 95 103 58 80 secondary chloride 0 -8 -30
tertiary 91 103 58 79 tertiary chloride 0 -12 -33
    H-Br Br-Br C-Br        
methane 104 88 46 70 methyl bromide 0 16 -8
primary 98 88 46 68 primary bromide 0 10 -12
secondary 95 88 46 68 secondary bromide 0 7 -15
tertiary 91 88 46 65 tertiary bromide 0 3 -16
    H-I I-I C-I        
methane 104 71 36 56 methyl iodide 0 33 13
primary 98 71 36 53 primary iodide 0 27 10
secondary 95 71 36 53 secondary iodide 0 24 7
tertiary 91 71 36 50 tertiary iodide 0 20 6

Table of Relative Rates of Free-Radical Halogenations

Halogen Methane Primary Secondary Tertiary
F2 0.5 1 1.2

1.4
Cl2 0.004 1 4 5
Br2 0.002 1 80 1700

 

 

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