Why para toluidine is more basic than meta toluidine?
Answers
HELLO THERE!
What determines the basic property of an organic compound?
Answer: It's power to donate it's lone pair electrons.
Now, we have p-toluidine and m-toluidine.
The NH₂ group has a lone pair, which is to be donated, for the compound to act as a base. Now, if this lone pair engages in resonance with the benzene ring, then this can't be donated and the base, hence will be weak.
CH₃ group has +I effect, which is more when it is attached in para position. As the CH₃ groups shifts electrons towards the benzene ring from para position in p-toluidine, the electron density of the ring increases, and so te lone pair of N is readily available, which makes it a good base than m-toluidine, in which the CH₃ group attached in meta position cannot show +I effect strongly, and the lone pair is engaged in resonance.
That's your answer. Refer to the attachment to get the structures. Thanks!
