When 3-chloro-4-fluoronitrobenzene is treated with 1 equivalent of sodium methoxide in methanol, the major product formed is:

Step-by-step solution

Nucleophilic aromatic substitution (SNAr) requires a strong electron-withdrawing group (like -NO ₂ ) at the ortho or para position relative to the leaving group to stabilize the carbanion intermediate. In 3-chloro-4-fluoronitrobenzene, the fluorine atom is at the para position with respect to the -NO ₂ group, while the chlorine atom is at the meta position. The -NO ₂ group strongly activates the para position via both -M and -I effects, but only weakly activates the meta position via its -I effect. Furthermore, in