Why can't hexane or toluene solutions dissolve in aqueous bromine?

[redpower]

I have just carried out a lab experiment today and desperately need some help!

1. The Experiment:

In my experiement I attempted to mix a solution of hexane with aqueous bromine. I started off by adding 15 drops of bromine into a test tube and then added 7 drops of hexane ontop of that. Prior to shaking, I could see two distinct colours in the test tube separated by a meniscous: the yellow bromine liquid lied at the bottom and the clear + colourless hexane solution lied on top of the bromine. After shaking, something odd happened. The two layers switched places => bromine ended up on top and hexane resided at the bottom of the test tube. The two colours were still distinct and separated by a meniscous. (The same thing happened when I tried to mix toluene with bromine)


2. What I discovered

Seeing that these two solutions would not dissolve each other, I concluded that one of them must be polar and the other must be non-polar. (We have previously learned that only "like dissolves like") HOWEVER, after analysing the substances, I realized that hexane (a hydrocarbon) and bromine are BOTH NON-POLAR SUBSTANCES. If that is the case, they should have dissolved each other - but they didn't! Thus, I am in a dilemma right now and have no idea how to approach this lab.

Any help would be greatly appreciated! Thank you in advance!

 

[MrCoffee2004]

Aqueous bromine is bromine dissolved in a water based solution. Usually HBr and H20. Your bromine preparation did not mix with either hexane or toluene because of their non-polar nature. They are non-miscible with water. Gaseous bromine, either Br2(g) or HBr(g), would dissolve however.

 

[Borek]

Aqueous bromine is bromine dissolved in a water based solution. Usually HBr and H20.

HBr in bromine solution? Some amount being produced in disproportionation - for sure, but this is not the main form of Br₂ present.

 

[MrCoffee2004]

I don't think that is right. If it were, the Br2 would have dissolved into the hexane or toluene. The Br was in an ionic state in the aqueous solution and that is why it didn't dissolve.

 

[Borek]

If it was ionic, how come solution was red?