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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: xshadow on November 09, 2020, 09:11:09 AM

Title: Possible alternative product for this exercise/reaction?
Post by: xshadow on November 09, 2020, 09:11:09 AM

Hi...I think that it  could also happen the B pathway.
So I may get a mixture..

(https://i.imgur.com/mv7H8AS.jpg)

According to us has it sense?
Thanks!


Think H2/Ni or  Zn/HCl  reductions are better here...

Title: Re: Possible alternative product for this exercise/reaction?
Post by: sjb on November 09, 2020, 11:13:15 AM

Is nucleophilic attack on a benzene ring favourable?

Title: Re: Possible alternative product for this exercise/reaction?
Post by: xshadow on November 09, 2020, 11:58:09 AM

Quote from: sjb on November 09, 2020, 11:13:15 AM

Is nucleophilic attack on a benzene ring favourable?

Usually not...
Buy I've studied that could happen when I have an halide a strong electron withdrawing group on the ring (carbonyl,NO2...)

Title: Re: Possible alternative product for this exercise/reaction?
Post by: spirochete on November 15, 2020, 03:51:28 PM

What you're describing (addition/elimination mechanism for NAS) can only happen if the electron withdrawing group is in the ortho or para position relative to the leaving group. In these cases, you can create a resonance stabilized anion intermediate where the negative charge/lone pair is delocalized onto the electronegative atom in the electron withdrawing group.