Match the compounds given in List-I with their characteristic reactions given in List-II. Select the correct option.

List – I (Compounds) (1) $CH_3CH_2CH_2CH_2NH_2$ (2) $CH_3C \equiv CH$ (3) $CH_3CH_2COOCH_3$ (4) $CH_3CH(OH)CH_3$

List – II (Reactions) (i) Alkaline hydrolysis (ii) With KOH (alcohol) and $CHCl_3$ produce a bad smell (iii) Gives white ppt. with ammoniacal $AgNO_3$ (iv) With Lucas' reagent cloudiness appears after 5 minutes

1. $CH_3CH_2CH_2CH_2NH_2$ (Primary Amine): Aliphatic primary amines react with chloroform ($CHCl_3$) and alcoholic KOH to form isocyanides (carbylamines), which have a foul smell. This is the Carbylamine test. Matches with (ii).
2. $CH_3C \equiv CH$ (Terminal Alkyne): Terminal alkynes possess an acidic hydrogen atom. They react with ammoniacal silver nitrate (Tollens' reagent) to form a white precipitate of silver alkynide [1]. Matches with (iii).
3. $CH_3CH_2COOCH_3$ (Ester): Esters undergo hydrolysis in the presence of an alkali (alkaline hydrolysis or saponification) to form carboxylate salts and alcohol. Matches with (i).
4. $CH_3CH(OH)CH_3$ (Secondary Alcohol): Reacts with Lucas reagent (conc. HCl and anhydrous $ZnCl_2$). Secondary alcohols produce turbidity (cloudiness) due to the formation of alkyl halide after about 5 minutes (slower than tertiary, faster than primary). Matches with (iv).

Therefore, the correct matching is (1)-(ii), (2)-(iii), (3)-(i), (4)-(iv).