33490
Propane-1,3-diol on reaction with SOCl2 should form 1,3-dichloropropane; a reaction similar to monohydric alcohol where OH is replaced by Cl.
The mechanism is as follows
..
R¾O¾H + O=S(¾Cl)¾Cl ® R¾O+¾H
½
O-¾S¾Cl ® R¾O¾S(¾Cl)=O + HCl
½
Cl
SN2
H+Cl- + R¾O¾S(¾Cl)=O ® Cld-?.R?.Od-¾S(¾Cl)=O
®RCl + O-¾S(¾Cl)=O ® SO2+ Cl-
Moderation Team
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