[BillJames]

Hey there, I've been googling for the past few hours, but still I couldn't figure out an answer.

My prediction: It's because water molecule, with the oxygen being a nucleophile, can potentially attack the sulfur entity of the starting material, resulting in side products. Chlorine is a good leaving group is my reasoning.

Starting material: http://www.tciamerica.com/common/img-structure/A0074.gif

Right?

[BillJames]

http://umbcnotes.f-sw.com/chem%20352L%20notes/Lab10/Synthesis%20of%204-Acetamidobenzenesulfonamide%20Notes.PDF

Answer found FINALLY.

Thanks guys