[The apprentice]

Good morning everyone, I'm studying chemistry and I came across the following problem. If possible, someone could teach me how to solve it (step by step)

Starting from hex-3-ene how should I make a Br2 addition mechanism?

[Babcock_Hall]

What are your initial thoughts?  For example, are there intermediates? 

[The apprentice]

What are your initial thoughts?  For example, are there intermediates?

well I first compare the type of Br-Br bond, then I broke the double bond.then I put both in each carbon

[Babcock_Hall]

When you broke the double bond, what intermediate did you obtain?

[The apprentice]

When you broke the double bond, what intermediate did you obtain?

well I'll break the double bond to put the two BR in the bond but I'm not sure if it's right or what I'm doing

sorry for the bad english

[Babcock_Hall]

It sounds to me as if you did everything in a single step, which is incorrect.  Let me give you a hint.  First one bromine adds, then the other bromine adds.  Why don't you post a drawing showing this?

[The apprentice]

It sounds to me as if you did everything in a single step, which is incorrect.  Let me give you a hint.  First one bromine adds, then the other bromine adds.  Why don't you post a drawing showing this?

This was my first drawing, but I think it's wrong

[Babcock_Hall]

A free carbocation is not formed in this reaction; instead, an intermediate with a formal positive charge on bromine in one resonance structure is formed.  Think about how many unshared pairs of electrons this particular bromine atom has.  When drawing this mechanism, it is also important to include correct curved arrows to and from this intermediate.