Match Organic Compounds with Their Characteristic Reactions

To find the characteristic reactions of each compound, we analyze the functional groups present in each compound of Column I and evaluate their behavior with each reagent/condition in Column II:

1. Compound (A): $\text{CH}_3\text{CH}_2\text{CH}_2\text{CN}$ (Butanenitrile)
   • (p) Reduction with $\text{Pd}-\text{C}/\text{H}_2$: Nitriles are catalytically hydrogenated in the presence of $\text{Pd}-\text{C}/\text{H}_2$ to yield primary amines:
     $\text{CH}_3\text{CH}_2\text{CH}_2\text{CN} + 2\text{H}_2 \xrightarrow{\text{Pd}-\text{C}} \text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{NH}_2$
   • (q) Reduction with $\text{SnCl}_2/\text{HCl}$: Nitriles undergo the Stephen reduction with $\text{SnCl}_2$ and $\text{HCl}$ followed by hydrolysis to form aldehydes:
     $\text{CH}_3\text{CH}_2\text{CH}_2\text{CN} \xrightarrow[\text{(ii) } \text{H}_3\text{O}^+]{\text{(i) } \text{SnCl}_2/\text{HCl}} \text{CH}_3\text{CH}_2\text{CH}_2\text{CHO}$
   • (s) Reduction with DIBAL-H: Diisobutylaluminium hydride reduces nitriles selectively to an imine intermediate, which upon aqueous workup yields an aldehyde:
     $\text{CH}_3\text{CH}_2\text{CH}_2\text{CN} \xrightarrow[\text{(ii) } \text{H}_2\text{O}]{\text{(i) DIBAL-H}} \text{CH}_3\text{CH}_2\text{CH}_2\text{CHO}$
   • (t) Alkaline hydrolysis: Nitriles readily hydrolyze in basic medium to form the corresponding carboxylate salt and ammonia:
     $\text{CH}_3\text{CH}_2\text{CH}_2\text{CN} + \text{OH}^- + \text{H}_2\text{O} \to \text{CH}_3\text{CH}_2\text{CH}_2\text{COO}^- + \text{NH}_3$
   • Therefore, $(\text{A}) \to (\text{p}, \text{q}, \text{s}, \text{t})$.

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1. Compound (B): $\text{CH}_3\text{CH}_2\text{OCOCH}_3$ (Ethyl acetate, an ester)
   • (s) Reduction with DIBAL-H: Esters are reduced by DIBAL-H at low temperature ($-78^\circ\text{C}$) to give aldehydes:
     $\text{CH}_3\text{COOCH}_2\text{CH}_3 \xrightarrow[\text{(ii) } \text{H}_2\text{O}]{\text{(i) DIBAL-H}} \text{CH}_3\text{CHO} + \text{CH}_3\text{CH}_2\text{OH}$
   • (t) Alkaline hydrolysis: Esters undergo saponification (alkaline hydrolysis) to form a carboxylate salt and an alcohol:
     $\text{CH}_3\text{COOCH}_2\text{CH}_3 + \text{OH}^- \to \text{CH}_3\text{COO}^- + \text{CH}_3\text{CH}_2\text{OH}$
   • Therefore, $(\text{B}) \to (\text{s}, \text{t})$.

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1. Compound (C): $\text{CH}_3-\text{CH}=\text{CH}-\text{CH}_2\text{OH}$ (But-2-en-1-ol, an unsaturated alcohol)
   • (p) Reduction with $\text{Pd}-\text{C}/\text{H}_2$: The carbon-carbon double bond undergoes catalytic hydrogenation to give the saturated alcohol (butan-1-ol):
     $\text{CH}_3-\text{CH}=\text{CH}-\text{CH}_2\text{OH} + \text{H}_2 \xrightarrow{\text{Pd}-\text{C}} \text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{OH}$
   • Therefore, $(\text{C}) \to (\text{p})$.

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1. Compound (D): $\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{NH}_2$ (Butan-1-amine, a primary amine)
   • (r) Development of foul smell on treatment with chloroform and alcoholic $\text{KOH}$: Primary amines undergo the carbylamine reaction (isocyanide test) to produce extremely foul-smelling alkyl isocyanides:
     $\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{NH}_2 + \text{CHCl}_3 + 3\text{KOH} \to \text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_2\text{NC} + 3\text{KCl} + 3\text{H}_2\text{O}$
   • Therefore, $(\text{D}) \to (\text{r})$.

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Final Matching:

• $(\text{A}) \to (\text{p}, \text{q}, \text{s}, \text{t})$
• $(\text{B}) \to (\text{s}, \text{t})$
• $(\text{C}) \to (\text{p})$
• $(\text{D}) \to (\text{r})$