Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes
Identify the correct order of reactivity of the following compounds towards nucleophilic aromatic substitution ( S_NAr ): (I) (II) (III)
Options
- A(I) > (II) > (III)
- B(I) > (III) > (II)
- C(II) > (III) > (I)
- D(III) > (I) > (II)
Correct answer
B. (I) > (III) > (II)
Step-by-step solution
Nucleophilic aromatic substitution ( S_NAr ) proceeds via an addition-elimination mechanism, forming a carbanion intermediate (Meisenheimer complex). The reactivity depends on two main factors: 1. The presence of electron-withdrawing groups (EWGs) at ortho and para positions, which stabilize the intermediate carbanion and increase reactivity. Conversely, electron-donating groups (EDGs) destabilize the intermediate and decrease reactivity. 2. The nature of the leaving group. For S_NAr , the reactivity order of halog