Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes
Arrange the following compounds in decreasing order of their reactivity towards nucleophilic aromatic substitution ( S_NAr ): (I) (II) (III)
Options
- A(II) > (III) > (I)
- B(I) > (III) > (II)
- C(III) > (I) > (II)
- D(I) > (II) > (III)
Correct answer
A. (II) > (III) > (I)
Step-by-step solution
The reactivity of aryl halides towards nucleophilic aromatic substitution ( S_NAr ) depends on the stability of the carbanion intermediate formed during the reaction. Electron-withdrawing groups stabilize this intermediate and increase the rate of reaction. A nitro group at the ortho or para position with respect to the leaving group stabilizes the intermediate strongly through both resonance ( -M ) and inductive ( -I ) effects. A nitro group at the meta position stabilizes the intermediate only through the weaker