December 01, 2020, 10:23:11 PM
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Topic: Possible alternative product for this exercise/reaction?  (Read 184 times)

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Offline xshadow

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Possible alternative product for this exercise/reaction?
« 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..



According to us has it sense?
Thanks!


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

Offline sjb

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Re: Possible alternative product for this exercise/reaction?
« Reply #1 on: November 09, 2020, 11:13:15 AM »
Is nucleophilic attack on a benzene ring favourable?

Offline xshadow

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Re: Possible alternative product for this exercise/reaction?
« Reply #2 on: November 09, 2020, 11:58:09 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...)

Offline spirochete

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Re: Possible alternative product for this exercise/reaction?
« Reply #3 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.

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