Which of the following cannot be made directly from a simple electrophilic aromatic substitution reaction with benzene?Question 3

🔍 What Is an Electrophilic Aromatic Substitution (EAS)?

EAS is a common method to functionalize benzene by replacing a hydrogen with an electrophile. Common electrophiles include NO₂⁺, R⁺ (carbocations), and halogens.

✅ Which Compounds Can Be Made via EAS?

• Nitrobenzene → Formed by nitration of benzene using HNO₃ and H₂SO₄.
• Isopropylbenzene (cumene) → Formed by Friedel–Crafts alkylation using propene + H⁺ or isopropyl chloride + AlCl₃.
• t-Butylbenzene → Formed via Friedel–Crafts alkylation using t-butyl chloride and AlCl₃.

🚫 What Cannot Be Made Directly?

• Aminobenzene (aniline) → Cannot be made directly from benzene via EAS.
• This is because the direct substitution of an amino group (–NH₂) is not feasible due to its basic nature and poor leaving group behavior.
• Instead, the typical route is:
  1. Nitration of benzene → nitrobenzene
  2. Reduction of nitrobenzene → aniline

✅ Final Answer: