[cyborgarm]

Suppose there is a benzene based molecule with 2 attached groups.
One is an ether group (an oxygen attached directly to the ring with a methyl group attached to the other side of the oxygen)
The other is a a propene group with a terminal double bond

Given this information would HX (where X is some halogen) react with the alkene to form an alkane chain with the halide in it, or would it somehow react with the ether group?

Also, would these results change if the propene group had the double bond in a non - terminal position?

Finally, if the ether group is attacked instead, what is an alternative method to saturate the double bond in the propene group (ideally with a halogen)?

Thanks in advance for your help

[Fridushka]

Please show some work ..

[cyborgarm]

This is not a homework problem or anything....  just for funsies

Anywho, according to my textbook, the hydrohalogenation adds a H and some halide over a double bond. 
alkene + HX -> halogenated alkane
The hydrogen from the halogen acid is attached first to the least substituted carbon.  This results in a carbon anion of second degree.  Then the remaining halogen ion attaches itself to the carbon anion completing the reaction.

Basically what I was wondering is if another group on the molecule, in this case an ether group (-O-CH3) would be attacked instead by the acid and interfere with the reaction and if so, how this could be avoided.

[mpierc18]

The HX will split the ether if the reaction is performed HOT. If performed COLD, it will add to the double bond.

[Dan]

This thread is >4 years old - please don't resurrect old threads.

[mpierc18]

I was searching to see if someone had posted a similar question in the past as to what I just asked - about HX addition to alkenes and possible PTC's (which no one can seem to answer btw... which is sad for a chemical forum). I found a question I could answer while researching my own question and thought that just in case someone has a similar question in the future, there would be an answer to reference. In regard to my question about using acetone as a PTC for HX addition to alkenes, I have searched the entire ACS database and have found nothing and was hoping someone on here had maybe attempted the same reaction...

Furthermore, if one should not resurrect old threads, the forum shouldn't allow you to do so. This particular forum question was unanswered, so I answered it. This IS a scientific forum after all and the ACS database goes back to the 1800's. Questions, no matter how old, are still questions and deserve answers. I just figured from a scientific standpoint, holding a chemistry degree from the University of North Carolina pursuing a M.S. ChemE from NCSU, that I was qualified to answer the question. So I answered it...

Sorry if this offends you. I'm not trolling, just looking for answers and so are other people. I was, which is why the old thread was resurrected. There was no answer to the question. I joined this forum to get results, not have people tell me about thread resurrection. I answered a forum question which had been unanswered for 4 years. Props to me. ;-)

I also scored in the 98th percentile on my standardized organic chemistry ACS exam.

The thread was resurrected because I had an EXTREMELY similar question and this thread has remained unanswered for 4 years. Until I answered it. Now someone PLEASE answer MY question... I would be eternally grateful.

[Dan]

Furthermore, if one should not resurrect old threads, the forum shouldn't allow you to do so.

I take this point and will raise it elsewhere.

Forum policy regarding thread resurrection is not dependent on your CV.

If you would like to continue this conversation, please start a new topic in "Comments to/from staff".