Medium Practice — Set 2

Quick Recap — Basicity Reasoning & Synthesis

• Aqueous basicity (methyl): $(CH_3)_2NH>CH_3NH_2>(CH_3)_3N>NH_3$; gas phase: $3^\circ>2^\circ>1^\circ>NH_3$.
• Aniline weaker than $NH_3$; substituent effects: EDG ($-CH_3$, $-OCH_3$) raise, EWG ($-NO_2$) lower basicity.
• Distinguish amine classes (Hinsberg, $HNO_2$, carbylamine); diazonium is a versatile synthetic intermediate.
• Aniline is o/p directing but its Friedel-Crafts and nitration require protection (acetylation).