[peacefulltortoise]

Here is my question:
In this part of glycerine synthesis reaction:
CH2Cl-CH=CH2 + Cl2 + H2O --> CH2Cl-CHOH-CH2Cl + HCl

I guess this is an AE reaction so I have 2 mechanisms here, please tell me which one is better or provide me one if none of them are right:

Mechnism1:
The electrophile Cl-Cl attacts "en" with its positive pole to make a cacbonium, then any negative agent (Cl-, OH2) in the solution could be add to cacbonium to make the product.
Mechanism 2:
First Cl2 + H2O --> HCl + HClO
Then HO-Cl + CH2=CH-CH2Cl -->CH2Cl-CHOH-CH2Cl, the electrophile is the positive pole (Cl) of Cl-OH, then any negative agent (Cl-, OH-) in the solution could be add to cacbonium to make the product.

So why the main product is neither CH2Cl-CHCl-CH2OH nor CH2Cl-CHCl-CH2Cl ?

Thanks for any reply.

[HP]

Old industrial synthesis glycerin is by this reaction scheme:
CH3CH=CH2 + Cl2 -->CH2(Cl)-CH=CH2 Sr reaction at 600C
THe formed alyl chloride (lacrymator) is then saponificated with NaOH /H2) to alyl alcohol CH2(OH)-CH=CH2 then it react with Cl2/H20 which is in equilibrium with forming HOCl and HCl formed. HOCl is added to + bond forming the chlorohydrine aduct CH2(OH)CH(Cl)CH2OH .This thn is saponificated again with NaOH(which is in excess in situ) to the final glycerin. Its interesting what happen with the formed HCl insted - does it react by Ae mechanism with the alyl alcohol? The answer is yes it may react to and this is comprehensive side reaction. You'll say how to transfer the formed by that reaction product to glycerine too Thats why this inndustrial process is alredy shifted by themost selective process starting from alyl chloride --> epichlorhydrine +NaOH/H2O --> directly glycerol. And also by the Harsh synthesis starting from alyl alcohol with H2O2: CH2=CHCH2OH + H2O2 --> glycerol
Its interesting to sugest that when having HOCl and HCl in the first scheme then may be possible these reactions similar to Harash process when peroxides form radical which further react with HCl in initial period i mean:
R-O-O-R --> 2R-O.
RO. + HBr (in original scheme) --> ROH + Br.
Then the formed Br. radical Ar react with alkenes
Br. + C=C --> R2C(Br)-C. (R2)
 R2C(Br)-C. (R2) + H-Br --> R2C(Br)-CH(R2) + Br.
Do you think its possible similar reaction when HOCl play similar role of peroxide i mean:
H-OCl --> HO. + Cl.
HO. + H-Cl --> H2O + Cl.
Thinking about this.
Salutes,
HP