Radicals/halogenation

[bigreiski]

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Since halogens are an electron withdrawing group, do they make the the hydrocarbon more acidic, AKA does the C-H bond gets weaker after halogenation? However, C-X bond is the weakest since the alkyl halide won't undergo a second halogenation. I would think that the EW group would make the compound more acidic, the strength of C-H bond would decrease and C would lose a H easier, but it loses the halogen easier, why is that?

 

[Cawolf]

I think the relative bond dissociation energies are so different in Bromine that you only see a small percent yield of the dibrominated product.

With Chlorine it is common to see chloromethane, DCM, chloroform, and Carbon tetrachloride.

It does make the proton more acidic, but the pka of methane is around 48 to begin with.