Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Arrange the following compounds in decreasing order of their rate of electrophilic aromatic substitution with CH ₃ COCl in the presence of anhydrous AlCl ₃ : (I) (II) (III)
Options
- AII > III > I
- BIII > II > I
- CI > III > II
- DIII > I > II
Correct answer
B. III > II > I
Step-by-step solution
The rate of electrophilic aromatic substitution depends on the electron density of the benzene ring. Electron-donating groups (activating groups) increase the electron density and thus the rate of reaction, while electron-withdrawing groups (deactivating groups) decrease the electron density and the rate of reaction. Let us analyze the substituent effects in the given compounds: (I) Methyl benzoate contains an ester group ( - COOCH ₃ ), which is a strongly deactivating group due to its strong -R and -I effects. It