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Potassium Dichromate

An organic co...

Question

An organic compound $A$ with molecular formula $C_{2} H_{7} N$ on reaction with nitrous acid gives a compound $B$ . $B$ on controlled gives compound $C$ . $C$ reduces Tollen's reagent to given silver mirror and $D$ . $B$ reacts with $D$ in the presence of concentrated sulphuric acid to give sweet smelling compound $E$ . Identify $A, B, C, D$ and $E$ . Give the reaction of $C$ with ammonia?

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Solution

The compounds A,B,C,D and E are ethyl amine $C_{2} H_{5} {N H}_{2}$ , ethanol $C_{2} H_{5} O H$ , ethanal ${C H}_{3} C H O$ , ethanoic acid ${C H}_{3} C O O H$ and ethyl acetate ${C H}_{3} C O O C_{2} H_{5}$ .
Ethylamine on reaction with nitrous acid gives ethanol.
$C_{2} H_{5} {N H}_{2} H N O_{3} - --- \to C_{2} H_{5} O H$
Ethanol on controlled oxidation gives acetaldehyde.
$C_{2} H_{5} O H controlled oxidation - ----------- \to C H_{3} C H O$
Acetaldehyde reduces Tollen's reagent to given silver mirror and ethanoic acid.
$C H_{3} C H O + 2 [A g (N H_{3})_{2}]^{+} + 3 O H^{-} heat - - \to C H_{3} C O O^{-} + 2 A g ↓ + 2 H_{2} O + 4 N H_{3}$
Ethanol reacts with ethanoic acid in the presence of concentrated sulphuric acid to give sweet smelling compound ethyl acetate.
$C_{2} H_{5} O H + C H_{3} C O O H conc sulphuric acid - ---------- \to C H_{3} C O O C_{2} H_{5}$
The reaction of ethanal with ammonia is as shown in image.

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