Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Arrange the following compounds in the decreasing order of their rate of electrophilic aromatic nitration with a mixture of HNO ₃ and H ₂ SO ₄ : (I) (II) (III)
Options
- A(I) > (III) > (II)
- B(II) > (III) > (I)
- C(I) > (II) > (III)
- D(III) > (I) > (II)
Correct answer
A. (I) > (III) > (II)
Step-by-step solution
The rate of electrophilic aromatic substitution (such as nitration) depends on the electron density of the benzene ring. Electron-donating groups activate the ring and increase the rate, while electron-withdrawing groups deactivate the ring and decrease the rate. Let us analyze the substituent groups in the given compounds: 1. In compound (I), the - OCH ₃ group is strongly activating due to its strong +M (mesomeric) effect, which significantly increases the electron density on the ring. 2. In compound (III), the -