Consider the following reaction sequence: . What is the final major organic product 'Z'? — Amines Chemistry Question
Question
Consider the following reaction sequence: $CH_3Cl \xrightarrow{KCN} \text{Product X} \xrightarrow{LiAlH_4} \text{Product Y} \xrightarrow{NaNO_2 / HCl, 0^\circ C} \text{Product Z}$. What is the final major organic product 'Z'?
💡 Solution & Explanation
$CH_3Cl$ reacts with $KCN$ via $S_N2$ to form methyl cyanide/acetonitrile ($CH_3CN$, Product X). Complete reduction of $CH_3CN$ with $LiAlH_4$ yields ethanamine ($CH_3CH_2NH_2$, Product Y). Reaction of this primary aliphatic amine with nitrous acid ($NaNO_2 + HCl$) generates a highly unstable aliphatic diazonium salt, which decomposes into an ethyl carbocation that reacts with water to form ethyl alcohol ($CH_3CH_2OH$, Product Z) with quantitative evolution of $N_2$ gas.