$word_{count}$: 220

Step 1 — Solubility classification: Soluble in water → polar, low MW (alcohols, acids, amines < C5). Soluble in NaOH but not NaHCO3 → phenol (weakly acidic). Soluble in both NaOH and NaHCO3 → carboxylic acid (strong enough to release CO2 from NaHCO3). Soluble in HCl → amine (basic). Insoluble in all → neutral, non-polar. Step 2 — Unsaturation: Br2/CCl4 decolorization → C=C or C≡C present. Baeyer's test (KMnO4 decolorization) → same. Aromatic rings do NOT decolorize either reagent. Step 3 — Carbonyl tests: 2,4-DNP positive → C=O present (aldehyde OR ketone). Then: Tollens' positive → aldehyde. Tollens' negative + 2,4-DNP positive → ketone. Fehling's positive → aliphatic aldehyde (aromatic aldehydes negative). Iodoform positive → methyl ketone or CH3CHO. Step 4 — Acid/base: NaHCO3 effervescence → -COOH. FeCl3 color → phenol. Na metal + H2 gas → -OH (alcohol). Step 5 — Amines: Carbylamine $\frac{CHCl3}{KOH}$ → foul-smelling isocyanide → primary amine only. Hinsberg $\frac{PhSO2Cl}{NaOH}$: soluble product → 1 degree, insoluble → 2 degree, no reaction → 3 degree. This systematic approach, combined with elemental analysis (Lassaigne's test), identifies most organic compounds encountered in JEE qualitative analysis.