[chrisbb]

OK so I completed a reaction that I found in a journal...

Anisole + t-butyl Chloride (in presence of AlCl₃).
I am trying to figure out what my final product.. Here is what I have as a start.... not sure if it is right though.



Thanks.
C

[macman104]

That isn't exactly the mechanism, but you are correct, you will get a mixture of ortho and para product

http://www.chemhelper.com/friedelcrafts.html

[chrisbb]

OK, thats good
Is my final product looking correct though? Do I have too many carbons coming off of the ring, from the t-butyl chloride?

[macman104]

Yes, your structure is correct.  Try drawing the mechanism though and you can verify it is correct.  However, I would draw the ortho and para products separately, and not like you have done (draw one structure for each, don't combine them).

[chrisbb]

ok will do today.
thanks for your help

[Gregorian]

this question is very interesting

when i first saw the reaction i expected that the lone pairs of electrons on oxygen will attack the same carbon you attacked so that reaction will go via SNac, but the alkyl chloride is too bulky, so then I thought that maybe the reaction will undergo elimination ?! 

is that also valid :S or the activating effect of OCH3 will totally direct the reaction?

[chrisbb]

not sure about the first question, with the lone pair....
I do know that o-Methyl groups are o/p directing.

Thanks again.
C

[macman104]

No, the o-methyl group is not going to do any elimination, or sn2 (if it were possible).  The lone pair electrons are delocalized, so they aren't nearly as powerful for elimination or sn2.  However, the delocalization of the electrons still can direct the aromatic substitution.

[Gregorian]

No, the o-methyl group is not going to do any elimination, or sn2 (if it were possible).  The lone pair electrons are delocalized, so they aren't nearly as powerful for elimination or sn2.  However, the delocalization of the electrons still can direct the aromatic substitution.

thank you much