Organic Compounds Containing Nitrogen MCQ Questions & Answers in Organic Chemistry | Chemistry

Aliphatic primary amines react with $$NaN{O_2}$$  and $$HCl$$  to yield alcohols.
$${C_2}{H_5}N{H_2} + HN{O_2}\left( {NaN{O_2} + HCl} \right)$$       $$ \to {C_2}{H_5}OH + {N_2} + {H_2}O$$

\[\underset{\left( A \right)}{\mathop{C{{H}_{3}}CN}}\,\xrightarrow{\text{Reduction}}\underset{\left( B \right)}{\mathop{C{{H}_{3}}-C{{H}_{2}}}}\,-N{{H}_{2}}\xrightarrow{HONO}C{{H}_{3}}C{{H}_{2}}OH\]

No explanation is given for this question. Let's discuss the answer together.

Excess of $$HCl$$  is used to convert free aniline to aniline hydrochloride otherwise free aniline would undergo coupling reaction with benzenediazonium chloride.

\[\underset{\begin{align} & \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,I \\ & \text{Octet complete,} \\ & \text{6 covalent bond,} \\ & -ve\,\text{charge on }N \\ \end{align}}{\mathop{{{H}_{2}}C={{N}^{+}}={{N}^{-}}}}\,>\underset{\begin{align} & \,\,\,\,\,\,\,\,\,\,\,\,\,\,III \\ & \text{Octet complete,} \\ & \text{6 covalent bond,} \\ & -ve\,\text{charge on }C \\ \end{align}}{\mathop{{{H}_{2}}{{C}^{-}}-{{N}^{+}}\equiv N}}\,>\underset{\begin{align} & \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,II \\ & \text{Octet incomplete,} \\ & \text{5 covalent bond,} \\ & -ve\,\text{charge on }N \\ \end{align}}{\mathop{{{H}_{2}}{{C}^{+}}-N={{N}^{-}}}}\,>\underset{\begin{align} & \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,IV \\ & \text{Octet incomplete,} \\ & \text{5 covalent bond,} \\ & -ve\,\text{charge on }C \\ \end{align}}{\mathop{{{H}_{2}}{{C}^{-}}-N={{N}^{+}}}}\,\]

\[C{{H}_{3}}N{{H}_{2}}+HN{{O}_{2}}\to C{{H}_{3}}OH+{{N}_{2}}+{{H}_{2}}O\]

(A) and (B) both are aliphatic primary amines which on oxidation with $$KMn{O_4}$$  give carbonyl compound, (C) is aliphatic secondary amine which gives tetra-alkyl hydrazine.

If nucleophile occupies same position of the leaving group, product is called direct substitution product.
If nucleophile occupies adjacent position of the leaving group, product is called cine substitution product. Intermediate formed in this reaction is benzyne.