Hi, if you have a brominated hydrocarbon - how easy/what can you do to de-brominate this (back to the hydrocarbon)? Can this be done via some sort of ion exchange column?

 

Cheers,

 

P.

Nucleophilic substitution should do the trick

You can't do an ion exchange column because the bromine won't dissociate off of the the rest of the organic molecule, the way it would in a salt. Therefore, you don't have any ions to exchange.

 

YT (I think) is referring to something like LiAlH4, which will react as if it is H-. It will act as a strong nucleophile.

 

Just for my own amusement, you can also eliminate to form the double bond, and then hydrogenate.

this will also give you a better idea: http://en.wikipedia.org/wiki/Nucleophilic_substitution

Convert it to a Grignard reagent then electrophilic substitution of "MgBr+" by H+

Convert it to a Grignard reagent then electrophilic substitution of "MgBr+" by H+

 

I think I did this once.

 

Entirely unintentionally, of course

OK - Thanks for your comments and ideas. I thought this would be the case. I think I'm looking for something that doesn't exist - I want to be able pass a brominated hydrocarbon (12-15 chains long) over/through some kind of column or catalytic converter type thingy and return it to standard kerosene without too much fuss. I'm not sure if this is possible with the ease I am after.