Hard Practice — Advanced Set

Hard Practice — Chained Electronic-Effect Reasoning

Chain inductive ($\pm I$), resonance ($\pm M$) and hyperconjugation effects to rank acidity, basicity and intermediate stability; reason about aromaticity and isomer counting.

• Acidity: carboxylic acid $>$ phenol $>$ water $>$ alcohol; more/closer $-I$ groups raise it.
• Carbocation/radical stability $3^\circ>2^\circ>1^\circ$; resonance beats them (benzyl, allyl). Aromatic: planar, cyclic, conjugated, $(4n+2)\pi$.