Consider the following sequence of reactions: p-chloroaniline NaNO ₂, HCl, 0-5^ C (A) N-methylaniline, mildly acidic (B) CH ₃ COCl, pyridine (C) The total number of bonds in the major product (C) is ________.

Step-by-step solution

Step 1: p-chloroaniline undergoes diazotization with NaNO ₂ and HCl at 0-5^ C to form p-chlorobenzenediazonium chloride (A). Step 2: The diazonium salt (A) undergoes an electrophilic aromatic substitution (azo coupling) with N-methylaniline. The coupling occurs at the para position of N-methylaniline, yielding 4-(4-chlorophenylazo)-N-methylaniline (B). Step 3: Compound (B) is a secondary amine. It reacts with acetyl chloride ( CH ₃ COCl ) in the presence of pyridine to undergo N-acetylation, forming N-(4-(4-chlorop