Misconception 1: "Phenol undergoes nucleophilic reactions at the ring like alcohols undergo nucleophilic substitution." Correction: Phenol's ring is electron-rich due to -OH (resonance donation), so it undergoes electrophilic aromatic substitution (EAS), not nucleophilic substitution. The -OH in phenol does not participate in SN reactions at the ring carbon.

Misconception 2: "3° alcohol is most reactive in all reactions." Correction: 3° is most reactive in dehydration and Lucas test (SN1-based) but is LEAST reactive in oxidation (resistant to oxidation) and LEAST reactive in SN2-based reactions (steric hindrance).

Misconception 3: "Phenol is an alcohol with a benzene ring attached." Correction: Phenol has -OH directly on the ring carbon (Ar-OH), not on a side chain. This is fundamentally different — it makes phenol acidic (pKa ~10) unlike benzyl alcohol (pKa ~15), where -OH is on a $CH_{2}$ group adjacent to the ring.

Misconception 4: "Kolbe and Reimer-Tiemann reactions give the para product." Correction: Both give predominantly the ortho product. Kolbe gives ortho due to metal cation ($Na^{+}$) coordination; Reimer-Tiemann gives ortho due to the bulky :$CCl_{2}$ carbene orientation. Para product is a minor side product.

Misconception 5: "Williamson synthesis works with any alkyl halide." Correction: Only 1° alkyl halides give good yields via SN2. 2° and 3° halides give predominantly elimination products (alkenes) with the strong alkoxide base.