This summary presents the major reaction pathways as a structured process map with SMILES for all key molecules.

Central Molecules and SMILES:

• Ethanol (1° alcohol): SMILES:CCO
• Propan-2-ol (2° alcohol): SMILES:CC(O)C
• 2-Methylpropan-2-ol (3° alcohol): SMILES:CC(C)(C)O
• Phenol: SMILES:Oc1ccccc1
• Diethyl ether: SMILES:CCOCC
• Salicylic acid: SMILES:OC(=O)c1ccccc1O
• Salicylaldehyde: SMILES:O=Cc1ccccc1O
• Phenyl acetate: SMILES:CC(=O)Oc1ccccc1

Alcohol Reaction Pathways:

Phenol Reaction Pathways:

Phenol --[$Br_{2}$/$H_{2}O$]--> 2,4,6-tribromophenol (white ppt) Phenol --[NaOH]--> PhO^{-}$$Na^{+} --[$CO_{2}$, 125°C, 4-7 atm]--> Sodium salicylate --[$H_{3}O^{+}$]--> Salicylic acid Phenol --[$CHCl_{3}$/NaOH, reflux via :$CCl_{2}$]--> Salicylaldehyde Phenol --[$CH_{3}COCl$]--> Phenyl acetate

Ether Reaction Pathways:

RO^{-}$$Na^{+} + R'X (1°) --[SN2]--> R-O-R' (ether) R-O-R' + HI (excess) --[SN2]--> RI + R'I

Key Reagent Map (Quick Reference):

• PCC → mild oxidation (1° → CHO; 2° → ketone)
• $KMnO_{4}$/$K_{2}Cr_{2}O_{7}$ → strong oxidation (1° → COOH; 2° → ketone)
• $LiAlH_{4}$ → strongest reduction (RCOOH → RC$H_{2}O$H)
• $NaBH_{4}$ → mild reduction (RCHO/$R_{2}CO$ → alcohol only)
• $ZnCl_{2}$/HCl → Lucas test (turbidity indicates alcohol type)
• :$CCl_{2}$ (from $CHCl_{3}$/NaOH) → Reimer-Tiemann formylation