Match Organic Compounds with Specific Qualitative Chemical Identification Tests

To determine the correct matching between the compounds in List-I and the qualitative chemical identification tests in List-II, we analyze each compound and its characteristic reaction:

1. Compound A (Cyclohexanol):

   • Cyclohexanol is a secondary alcohol ($2^\circ$ alcohol).
   • Secondary alcohols react with Lucas reagent (a solution of anhydrous $\text{ZnCl}_2$ in concentrated $\text{HCl}$) to form alkyl chlorides, producing turbidity within 5 minutes.
   • Therefore, A matches with III (Lucas test).

2. Compound B (Cyclohexylamine):

   • Cyclohexylamine is a primary aliphatic amine ($1^\circ$ amine).
   • Primary amines react with Hinsberg's reagent (benzenesulfonyl chloride, $\text{C}_6\text{H}_5\text{SO}_2\text{Cl}$) to yield an $N$-alkylbenzenesulfonamide containing an acidic hydrogen, which dissolves in aqueous $\text{NaOH}$.
   • Therefore, B matches with I (Hinsberg's reagent test).

3. Compound C (Cyclohexanecarbaldehyde):

   • Cyclohexanecarbaldehyde contains an aldehyde functional group ($-\text{CHO}$).
   • Aldehydes readily reduce Tollen's reagent (ammoniacal silver nitrate, $[\text{Ag}(\text{NH}_3)_2]^+$) to metallic silver, forming a silver mirror on the inner walls of the test tube.
   • Therefore, C matches with IV (Tollen's test).

4. Compound D (Phenol):

   • Phenol reacts with phthalic anhydride when heated in the presence of concentrated $\text{H}_2\text{SO}_4$ to form phenolphthalein. Upon adding excess alkali ($\text{NaOH}$), a characteristic pink dye solution is produced.
   • Therefore, D matches with II (Phthalein dye test).

Combining the correct matches: $\text{A - III, B - I, C - IV, D - II}$

This corresponds to Option A.