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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

  1. AII > III > I
  2. BIII > II > I
  3. CI > III > II
  4. 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

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