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EAS question

dentalwhiz

Full Member
Jun 15, 2017
90
16
  1. Pre-Dental
    why does toulene give more ortho product than anisole during nitration? My notes say amines and methoxy groups are strong activators, while alkyl groups are weak activators. any insight?
     
    Last edited:

    1ysh

    Full Member
    2+ Year Member
    Dec 23, 2016
    236
    170
    1. Pre-Dental
      Anisole has a methoxy group with a strongly electronegative Oxygen, therefore contributing to the ortho directing group.
      Toulene, on the other hand, has just a methyl group with Carbon being not as electronegative as Oxygen, contributing less to the ortho directing group.
       
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      dentalwhiz

      Full Member
      Jun 15, 2017
      90
      16
      1. Pre-Dental
        Anisole has a methoxy group with a strongly electronegative Oxygen, therefore contributing to the ortho directing group.
        Toulene, on the other hand, has just a methyl group with Carbon being not as electronegative as Oxygen, contributing less to the ortho directing group.
        THANKS! Makes complete sense, I completely missed the ortho part and just was looking to see which is more activating.
         
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