Answer:
The answer is: p-aminotoluene; NaNO₂/HCl, 0⁰C; CuCl
Step-by-step explanation:
To prepare p-chlorotoluene from p-aminotoluene:
Diazotization reaction: This reaction is used form the preparation aryldiazonium salt from primary aromatic amines.
Therefore, p-aminotoluene is treated with NaNO₂/HCl at 0-5⁰C to prepare the aryl diazonium salt.
Sandmeyer reaction: This reaction is used for the preparation of aryl halides from aryl diazonium salts.
Therefore, the aryl diazonium salt formed by the diazotization reaction of p-aminotoluene, is heated with cuprous chloride to give p-chlorotoluene.