MS 913 - Benzene EAS Reactions, EDG/EWG, and ortho/meta/para Directors Submitted by Matt on August 6, 2011.

Textbook and Chapter: Carey and Giuliano 8th Ed. (2010), Chapter 12

Keywords: EAS mechanism, EDG and EWG, Friedel-Crafts

Description: Covers electrophilic aromatic substitution (EAS) reactions in detail.

It includes many, many resonance exercises that show why:

  • Electron donating groups (EDG) are ortho-para directors
  • Electron withdrawing groups (EWG) are meta-directors
  • Pyrrole undergoes EAS at C-2 and not C-3
  • Pyridine undergoes EAS at C-3 and not C-2 or C-4
  • Naphthalene undergoes EAS at C-1 and not C-2

Total Problems: 11

Problem # 722

Show how to prepare vinyl benzene from benzene.

Problem # 594

A chemist tried to prepare compound A from benzene via Friedel-Crafts alkylation and instead produced compound B.

Why did this happen? How could the chemist prepare compound A?