Question

Hydrolysis of \[C{H_3}C{H_2}N{O_2}\] with 85% \[{H_2}S{O_4}\] gives.
(a) \[C{H_3}C{H_2}OH\]
(b) \[{C_2}{H_6}\]
(c) \[C{H_3}CH = NOH\]
(d)\[C{H_3}COOH\]

Answer 1

Hint: The reaction involves the acid (\[HCl\] or \[{H_2}S{O_4}\]) hydrolysis of primary and secondary nitroalkanes to carbonyl compounds such as aldehydes, ketones, and acid.

Complete step-by-step answer:
The hydrolysis of nitroalkane with 85 % of \[HCl\] or \[{H_2}S{O_4}\] is an example of a Nef reaction. This reaction was first reported by John Ulric Nef (Swiss-born American chemist).
In this reaction, the primary nitro alkane (\[C{H_3}C{H_2}N{O_2}\]) is treated with 85 % of \[HCl\] or \[{H_2}S{O_4}\]to produce the carboxylic acid and hydroxylamine.
\[C{H_3}C{H_2}N{O_2} + {H_2}O + {H_2}S{O_4} \to C{H_3}COOH + N{H_2}OH\]
The reaction is also the cheapest way for manufacturing hydroxylamine (\[N{H_2}OH\] ). Hydroxylamine (\[N{H_2}OH\] )belongs to the class of inorganic compounds. It is a white color with a hygroscopic nature.
In the reaction, the secondary nitroalkane produces ketones and nitrous acid (\[{N_2}O\]). Whereas the tertiary nitroalkane does not undergo hydrolysis with \[HCl\] and \[{H_2}S{O_4}\] .
\[2{(C{H_3})_2}CHN{O_2} + {H_2}S{O_4} \to 2{(C{H_3})_2}C = O + {N_2}O + {H_2}O\]
The hydrolysis of nitro alkane can also be performed in the presence of Lewis acids such as chloride salt of \[Sn(IV)\] and\[Fe(III)\] or oxidizing agents such as Oxone.

Form the above statements stated that the hydrolysis of primary nitroalkane in the presence of 85 % of \[HCl\] or \[{H_2}S{O_4}\] can produce carboxylic acid and hydroxylamine. Therefore, the correct answer will be \[C{H_3}COOH\] and hence option (d) is the correct answer.

Note: The aqueous solution used as reaction medium for Nef reaction
Nitrous acid (\[{N_2}O\]) is commonly called laughing gas and it is used in the field of medicine as a sedative (to induce sleep).