Identify the final product (C) in the reaction given below; $CH_3CH_2I+ NaCN →A → \text{(Partial hydrolysis}/OH^-) → B + NaOH + Br_2 → C$? |
$CH_3CH_2OH$ $CH_3CH_2NH_2$ $CH_3CH_2CH_2NH_2$ $CH_3CH_2CH_2Br$ |
$CH_3CH_2NH_2$ |
The correct answer is Option (2) → $CH_3CH_2NH_2$ Step 1: Alkyl halide + NaCN The reaction of an ethyl halide with sodium cyanide follows an $S_N2$ mechanism, resulting in a nitrile. $\text{CH}_3\text{CH}_2\text{I} + \text{NaCN} \rightarrow \text{CH}_3\text{CH}_2\text{CN}$ Product A: Propionitrile (ethyl cyanide) Observation: The carbon chain length increases by one carbon. Step 2: Partial hydrolysis of nitrile Nitrile, on partial hydrolysis (usually using cold concentrated $\text{HCl}$ or alkaline $\text{H}_2\text{O}_2$), yields an amide. $\text{CH}_3\text{CH}_2\text{CN} \rightarrow \text{CH}_3\text{CH}_2\text{CONH}_2$ Product B: Propanamide Step 3: Reaction with $\text{Br}_2 + \text{NaOH}$ This is known as the Hofmann Bromamide degradation reaction. $\text{RCONH}_2 \overset{\text{Br}_2/\text{NaOH}}{\longrightarrow} \text{RNH}_2$ In this step, the carbonyl group is removed as a carbonate/$\text{CO}_2$ equivalent, resulting in an amine with one less carbon than the starting amide. $\text{CH}_3\text{CH}_2\text{CONH}_2 \rightarrow \text{CH}_3\text{CH}_2\text{NH}_2$ Final Product (C) The final product obtained after the degradation is Ethylamine. $\text{CH}_3\text{CH}_2\text{NH}_2$ |