Does ethyl benzoate react with bromine?

I think it should as carbons on the benze ring have carbon-carbon double bonds but in the question it says there's no change :s-smilie:

Reply 2

-Kav-

It's important to remember that benzene does not consist of 3 double bonds and 3 single bonds; that's just a mechanistically useful way to draw it. In reality, a single 'superorbital' across all the carbons is formed, containing all six ∏ electrons. This is an extremely stable set-up, and so whatever you're reacting with benzene has to be a damn sight more reactive than bromine for it to undergo addition in the manner you suggest.

Reply 3

trickz

Great advice. Thank you very much. Found it will need a catalyst and high temp to react with the benzene ring. I really have to stop seeing double bonds and realise it has a delocalised system of electrons!

Reply 4

-Kav-

No worries. As I say, so long as you remember the effect of the aromaticity, the resonance structures with the double bonds are much more useful, in spite of being a bit less true.