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EAS question

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dentalwhiz

Full Member
Jun 15, 2017
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  1. Pre-Dental
  • #1
      • 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?
       
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      1ysh

      Full Member
      2+ Year Member
      Dec 23, 2016
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      1. Pre-Dental
    • #2
        • 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
      • #3
          • jse122 said:
          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.
          Click to expand...
          THANKS! Makes complete sense, I completely missed the ortho part and just was looking to see which is more activating.
           
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