Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Arrange the following compounds in the decreasing order of their relative rate of electrophilic aromatic substitution (Friedel-Crafts alkylation) with isopropyl chloride in the presence of anhydrous AlCl ₃ : (i) (ii) (iii)
Options
- A(i) > (iii) > (ii)
- B(ii) > (iii) > (i)
- C(i) > (ii) > (iii)
- D(ii) > (i) > (iii)
Correct answer
D. (ii) > (i) > (iii)
Step-by-step solution
The rate of electrophilic aromatic substitution (such as Friedel-Crafts alkylation) depends on the electron density of the benzene ring. Electron-donating groups activate the ring by increasing electron density, while electron-withdrawing groups deactivate the ring by decreasing electron density. 1. In phenol (ii), the - OH group is a strongly activating group because its +M (resonance) effect is much stronger than its -I (inductive) effect. This makes the ring highly electron-rich and most reactive towards electro