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Question

Why is p toluidine more basic than m toluidine?

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Solution

In p-toluidine, the presence of electron-donating −CH3 group on the benzene ring increases the electron density on the N-atom of the amino group and thus the electron pair on nitrogen becomes more available for sharing with an acid.
But electron releasing group exerts greater base strengthening effect when present at para position.Therefore groups increase the electron density on nitrogen atom of NH2 group to graeter extent when present at para position.
Thus, p-toluidine is more basic.


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