Jun 15, 2017
90
16
Status
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?
 
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1ysh

2+ Year Member
Dec 23, 2016
236
158
Status
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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OP
D
Jun 15, 2017
90
16
Status
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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