Question

An alkyl hydroxylamine on heating with Tollen's reagent gets oxidised to the corresponding nitroso compound and the Tollen's reagent is itself reduced to metallic silver. This reaction is called:
a.) Baker-Mulliken test
b.) Wacker synthesis
c.) Reimer Tiemann reaction
d.) none of the above

Answer 1

Hint: The Tollen’s reagent is a chemical reagent which is used to determine the presence of an aldehyde or an aromatic aldehyde functional group along with the presence of some alpha hydroxy ketone group which can tautomerize and formaldehyde. Tollen’s reagent is a solution of silver nitrate i.e. $AgN{{O}_{3}}$ and ammonia i.e. $N{{H}_{3}}$

Complete step by step answer:
Baker Mulliken's test is use for the detection of the nitro group i.e.$-N{{O}_{2}}$. This test is based on the fact that the nitro group is reduced to the hydroxylamine group $-NHOH$ with the help of the neutral reducing agents. The formed hydroxyl amine compound reduces the Tollen’s reagent i.e. $[Ag{{(N{{H}_{3}})}_{2}}]OH$ and it itself gets oxidized into a nitroso compound.
The reduction of nitrobenzene with zinc in the presence of ammonium chloride produces N-phenyl hydroxylamine. When this N-phenyl hydroxylamine is treated with Tollen’s reagent there is formation of metallic silver.
The reactions involves is mentioned below:
\[RN{{O}_{2}}+4H+Zn+N{{H}_{4}}Cl\to RNHOH+{{H}_{2}}O\]\[RNHOH+Ag{{(N{{H}_{3}})}_{2}}OH\to RNO+2{{H}_{2}}O+2Ag+4N{{H}_{3}}\]

Hence the correct answer is option (A) i.e. an alkyl hydroxylamine on heating with Tollen's reagent gets oxidised to the corresponding nitroso compound and the Tollen's reagent is itself reduced to metallic silver. This reaction is called Baker-Mulliken test
So, the correct answer is “Option A”.

Note: The baker-Mulliken test can be performed for all the compounds containing nitroso groups not just nitrobenzene. The Ag released at the end of the reaction indicates that there is a nitro group present in the given compound.