We were asked to try out the mechanism for this organic conversion by using Ph2S:
I have two questions when it comes to the starting step which is Ph2S: attacking 1-chloro-3-iodo propane:
1) If I use Ph2S: why does it act as a nucleophile and attack CH2 ? Why can't it act as a Lewis base and abstract a proton from CH2?
2) I understand that Iodine is a better leaving group than Chlorine, but if we compare electrophilicity, the CH2 attached to Cl is more electrophilic(Cl being more electronegative than I), then why does the nucleophile(provided my first question is answered) attack CH2 next to Iodine? Is leaving group ability given more preference over the electrophilicity of CH2?