Question #44119

Consider the following multi-step reaction sequence involving diazo-coupling and degradation:

Step 1: $\text{Aniline} \xrightarrow[0-5^\circ\text{C}]{\ce{NaNO2 / HCl}} \text{A}$

Step 2: $\text{A} + \text{Aniline} \xrightarrow[0^\circ\text{C}]{\text{pH } \approx 6} \text{B (Major)}$

Step 3: $\text{B} \xrightarrow[40^\circ\text{C}]{\text{Aniline}\cdot\text{HCl (cat.)}} \text{C}$

Step 4: $\text{C} \xrightarrow[0-5^\circ\text{C}]{\ce{NaNO2 / HCl}} \text{D}$

Step 5: $\text{D} + \text{Salicylic acid} \xrightarrow{\text{pH 9-10}} \text{E (Major)}$

Step 6: $\text{E} \xrightarrow[\Delta]{\ce{SnCl2 / HCl (excess)}} \text{Mixture of aromatic amines}$

Identify the complete set of aromatic amines obtained in the final mixture.