Account for the following: aniline is a weaker base than cyclohexylamine.
Solution
In CHNH the nitrogen lone pair is shared with the π-system (resonance), and protonation destroys that stabilisation.
Cyclohexylamine's saturated ring offers no delocalisation — its lone pair is undiminished, and the +I ring even helps.
So cyclohexylamine ≫ aniline as a base.
Cyclohexylamine's saturated ring offers no delocalisation — its lone pair is undiminished, and the +I ring even helps.
So cyclohexylamine ≫ aniline as a base.
CBSE Class 12 Board · 2002 · Foreign · Subjective