N-Bromosuccinimide (NBS) is the standard reagent for allylic and benzylic bromination. Which of the — Haloalkanes and Haloarenes Chemistry Question
Question
N-Bromosuccinimide (NBS) is the standard reagent for allylic and benzylic bromination. Which of the following mechanistic statements correctly explain why NBS strictly favours substitution over electrophilic addition to the alkene double bond?
💡 Solution & Explanation
A) True. The mechanism relies on traces of $HBr$ reacting with NBS ($NBS + HBr \rightarrow Succinimide + Br_2$) to supply a tiny but constant stream of $Br_2$. B) True. Electrophilic addition across a double bond requires a relatively high localized concentration of $Br_2$ to form the bridged bromonium ion. At very low $Br_2$ concentrations, the allylic radical easily abstracts a $Br$ atom from $Br_2$, keeping the chain reaction viable and suppressing addition. C) False. The reaction is entirely a free-radical process initiated by light or peroxides, not electrophilic. D) False. Succinimide is merely a byproduct and plays no active protective role.