Question

Product (iii) in following equation is:
${C_2}{H_5}N{H_2}\xrightarrow[{Tilden}]{{reagent}}(i)\xrightarrow{{N{H_3}}}(ii)\xrightarrow[{NaN{O_2}}]{{HCL(dil)}}(iii) $
(A) Alcohol
(B) Ether
(C) Alkyl Chloride
(D) Alkyl Nitrite

Answer 1

Hint: Tilden Reagent is $ NOCl $ ( Aside from its role in the production of caprolactam, Tilden reagent finds some other uses in organic synthesis). Ethylamine appears as a colourless liquid or a gas (boiling point 62°F) with an odour of ammonia. During combustion, toxic nitrogen oxides are formed. When a closed container is exposed to extreme heat, it can violently rupture and rocket.

Complete answer:
By dissociating $ NOCl $ into $ N{O^ + } $ and $ C{l^ - } $ , ethyl amine reacts with Tilden reagent (nitrosyl chloride) to produce ethyl chloride (i).
Ions are a type of ion. Following the $ S{N_2} $ mechanism, the Cl ions replace the amine group in the reactant.
Finally, ethylamine (ii) is treated with hydrochloric acid in the presence of sodium nitrite to produce an unstable diazonium ethyl chloride, which reacts with water to produce ethanol (iii).
 $ {C_2}{H_5}N{H_2} $ is a reaction that shows the formation of alcohol from a primary amine.
 $ NOCl $ $ {C_2}{H_5}N{H_2}\xrightarrow[{Tilden}]{{reagent}}C{H_3}C{H_2}Cl\xrightarrow{{N{H_3}}}{C_2}{H_5}N{H_2}\xrightarrow[{NaN{O_2}}]{{HCL(dil)}}C{H_3}C{H_2}{N^ + } \equiv NCl\xrightarrow{{{H_2}O}}C{H_3}C{H_2}OH $
The correct option is (A) Alcohol.

Additional Information:
A diazo group is an organic group which consists of two nitrogen atoms linked together in the terminal position. The nitrogen atoms are termed –azo groups therefore the name di-azo. An amine will undergo diazotization when it reacts with sodium nitrite in presence of hydrochloric acid.

Note:
When primary aromatic amines are nitrosation with nitrous acid (produced in situ from sodium nitrite and a strong acid like hydrochloric acid, sulfuric acid, or HBF4), diazonium salts are formed, which can be isolated if the counterion is non-nucleophilic is called diazotization.