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Identify the compounds in the following.
C₂H₅CONH₂ xrightarrowBr₂/KOH [A] xrightarrowCHCl₃ + KOH [B] xrightarrowNa/C₂H₅OH [C]
$\text{C}_2\text{H}_5\text{CONH}_2 \xrightarrow{\text{Br}_2/\text{KOH}} [\text{A}] \xrightarrow{\text{CHCl}_3 + \text{KOH}} [\text{B}] \xrightarrow{\text{Na}/\text{C}_2\text{H}_5\text{OH}} [\text{C}]$
Answer
Answer
Equations: $\mathrm{C_{2}H_{5}CONH_{2}} + \mathrm{Br_{2}} + 4\mathrm{KOH} \longrightarrow \mathrm{C_{2}H_{5}NH_{2}} + \mathrm{K_{2}CO_{3}} + 2\mathrm{KBr} + 2\mathrm{H_{2}O}$ $\mathrm{C_{2}H_{5}NH_{2}} + \mathrm{CHCl_{3}} + 3\mathrm{KOH} \xrightarrow{\text{heat}} \mathrm{C_{2}H_{5}NC} + 3\mathrm{KCl} + 3\mathrm{H_{2}O}$ $\mathrm{C_{2}H_{5}NC} + 4\mathrm{[H]} \xrightarrow{\text{Na}\text{/}\mathrm{C_{2}H_{5}OH}} \mathrm{C_{2}H_{5}NHCH_{3}}$
A - ethanamine: CH3CH2NH2
B - isocyanoethane (ethyl isocyanide): CH3CH2NC
C - N-methylethanamine: CH3CH2NHCH3
[A] ethanamine (Hofmann bromamide reaction); [B] ethyl isocyanide (carbylamine reaction); [C] N-methylethanamine.