EAS question

[dentalwhiz]

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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?

 

[1ysh]

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.

 

[dentalwhiz]

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.