Aniline dissolved in dilute HCl is reacted wi | vedclass

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(A) $1$. Aniline reacts with $NaNO_2$ and $HCl$ at $0\,^oC$ to form benzenediazonium chloride $(C_6H_5N_2^+Cl^-)$.$2$. When this diazonium salt is add

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(A) $1$. Aniline reacts with $NaNO_2$ and $HCl$ at $0\,^oC$ to form benzenediazonium chloride $(C_6H_5N_2^+Cl^-)$.$2$. When this diazonium salt is added to a mixture of aniline and phenol in dilute $HCl$,the medium is acidic.$3$. In an acidic medium,the amino group of aniline is protonated to form an anilinium ion $(-NH_3^+)$,which is deactivating and does not undergo coupling.$4$. However,the diazonium salt reacts with aniline to form a diazoamino compound $(C_6H_5-N=N-NH-C_6H_5)$ in a slightly acidic or neutral medium,but in the presence of dilute $HCl$,the reaction with aniline is suppressed.$5$. The coupling reaction with phenol occurs in a basic medium. Since the medium is acidic,the coupling reaction is generally slow or inhibited for both.$6$. However,among the given options,the formation of the diazoamino compound $(C_6H_5-N=N-NH-C_6H_5)$ is the characteristic reaction of benzenediazonium chloride with aniline in the presence of dilute $HCl$ (where the aniline is not fully protonated or the reaction is kinetically favored).$7$. Therefore,the major product formed is the diazoamino compound.

Aniline dissolved in dilute $HCl$ is reacted with sodium nitrite at $0\,^oC$. This solution was added dropwise to a solution containing an equimolar mixture of aniline and phenol in dilute $HCl$. The structure of the major product is

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