reactor results of freidel-crafts alkylation(rearrangement?)

I am a chem. eng. undergrad, and I just figured out how to use Reactor. I think it is an amazing tool to test out reaction scenarios, but I have a few issues. Maybe it is due to my lack of understanding of the software, or possibly the chemistry, but should a primary alkyl halide undergo rearrangement during the freidel-crafts  alkylation of benzene to for a more stable metal complex. For instance when I run the F-C alklyation scheme in reactor with 1-chloropropane and benzene, I get propylbenzene as a result, but it should actually give isopropylbenzene as a result of the rearrangement. Am I missing something?

 

Thanks

Hi,

Thank you for your feedback, it's appreciated.

Few words about Reactor: this is a reaction enumeration engine, meaning that is able to enumerate products or reactions according to a predefined reaction equation and reaction rules. Those reaction rules help to detect activation/deactivation sites, regioselectivity, potential side reactions and so on.
You can find more information about Reactor here:
http://www.chemaxon.com/jchem/doc/user/reactor.html />http://www.chemaxon.com/jchem/doc/user/ReactorFAQ.html />http://www.chemaxon.com/jchem/doc/user/reactor_gui.html

The reaction library covers the most relevant organic chemical reactions, which are grouped according to mechanism. In case of Fiedel-Crafts alkylation reaction you are correct, we generate the minor product only. Using 1-chlorobutane and similar compounds as reagents, a large part of the product results from rearrangement (different mechanism), so I will expand the library with another F-C alkylation that provides the rearranged products.

Hope this helps,
Best,

Anna

Thanks for the reply. Like I said I am just a lowly
undergrad. I know many of the tools in the Jchem suite are capable of doing
things beyond my current understanding. Never the less I appreciate what I can
do with these tools. Marvin Sketch has been immensely helpful to me in my
classes, and now that I am taking organic II reactor has come in handy several
times to test out possible reagents in a specific mechanism. I only made the
comment because I noticed a conflict between what I had expected to see and
what reactor showed me the product to be.

 

Thanks again.

Is this F-C-rearrangement reaction available in the current library ?

Dear Ellert,

Yes, we have several Friedel-Crafts reactions defined in our library, the one you are looking for is called Friedel-Crafts alkylation.

Please note if the result of the transformation could be improved, or not exactly what you would expect let is us know. Happy to help to modify the reaction rules accordingly.

Regards,

Anna