Consider the addition of HBr (in absence of any radical initiators or environment that promotes radical mechanistic pathway), to 3-bromocyclopentene.

The first step is the attack of $\ce{H^+}$ On the exposed π electron cloud. But my query is whether it forms a classical carbocation like this one to oppose the negative inductive effects of the halogen atom:

Or does it proceed with the formation of bromonium ion like this one to partially complete its octet using lone pairs on Br.

These two would lead to different products but I'm interested in the major one. The first one would lead to 1,3-dibromocyclohexane, while the second one would lead to 1,2-dibromocyclohexane.

• Yeah, there should be bromonium here, but it's not what is called non-classical carbocation. – Mithoron Jan 19 '18 at 15:24
• But sir I have been told that the inductive effect is so strong that it lead the the 1st pathway. But I feel it should be the one with bromonium ion. As in anchimeric effects during substitution reactions. Is there a strong justification for that? – user50247 Jan 19 '18 at 15:33