Choose the Best Answer · Q18
Q.Which one of the following is most basic?
a) 2,4-dichloroaniline
b) 2,4-dimethylaniline
c) 2,4-dinitroaniline
d) 2,4-dibromoaniline
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Start your 14-day free trial to unlock the full solution →Step 1. A ring substituent's effect on aniline's basicity works through the same resonance/induction pathway that makes plain aniline itself less basic than ammonia: anything that makes MORE electron density available on nitrogen raises basicity, and anything that pulls electron density away lowers it.
Step 2. -CH3 (methyl) is electron-RELEASING (+I effect), so both methyl groups in 2,4-dimethylaniline push additional electron density toward the ring and, through it, keep more density available on nitrogen -- raising basic strength above plain aniline's. …
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