Question

Although chlorine is an electron withdrawing group yet it is ortho, para directing in nature. Why?

Answer 1

Chlorine withdraws electron through -I effect and donate electrons through +R effect ( Resonance ). Chlorine acts as o, p directing group because of resonance. One of the lone pair of electrons of chlorine can conjugate to the ring and direct the electrophile to the ortho and para positions of the ring.