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Is HBr a nucleophile?

1 Answer
Dec 4, 2015

Pretty much never.

A nucleophile MUST be a Lewis base, and there is a very poor chance that #"HBr"# will donate electrons BEFORE it donates its proton; its pKa is about #-9#, i.e. it's a pretty strong acid.

It is much, much more likely to give up a proton by accepting electrons. That just shows that it is a Lewis acid, NOT a Lewis base, and therefore it is an electrophile.