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Basic character of amines – aryl vs alkyl
Concepts tested here
- arylamine-basicity-resonance
All Questions
2016 1 question
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The correct statement regarding the basicity of arylamines is
Delocalisation of the N lone pair into the ring lowers basicity.
In alkylamines ($R\rightarrow\ddot{N}H_2$), the electron-releasing alkyl group increases electron density on nitrogen, so alkylamines donate the lone pair readily and are more basic.
In arylamines ($Ar-\ddot{N}H_2$), the lone pair on nitrogen is in conjugation with the ring (+M effect overpowers –I); it is delocalised into the ring and stabilised by resonance.
Therefore the tendency to donate the lone pair decreases, i.e. arylamines are less basic than alkylamines.
