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Mechanism of the Wohl-Ziegler Reaction

It is very important to keep the concentration of Br2 and HBr low to prevent side reactions derived from
simple ionic addition with the alkene. These reagents are therefore generated in situ from NBS. The
catalytically active species is Br2, which is almost always present in NBS samples (red colour).

A radical initiator (UV, AIBN) is needed for the homolytic bond cleavage of Br 2 :

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