Fundamentals of Organic ChemistryChemistryHaloalkanes and Haloarenes
Among the following compounds, which one is most readily hydrolyzed by aqueous alkali?
Correct answer
0
Step-by-step solution
The hydrolysis of aryl chlorides by aqueous alkali proceeds via the nucleophilic aromatic substitution ( S_NAr ) mechanism. The rate-determining step is the attack of the nucleophile ( OH^- ) on the carbon bearing the halogen, forming a negatively charged intermediate (Meisenheimer complex). The presence of electron-withdrawing groups (like -NO₂ ) on the benzene ring stabilizes this intermediate carbanion. This stabilization is most effective when the electron-withdrawing groups are at the ortho and/or para positio