Mechanism of glucose pentaacetate formation from acetyl chloride

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nil1996
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Homework Statement



can anybody explain the mechanism of the reaction



C6H12O6 +CH3COCl → CHO(CHOOCCH3)4CH2OOCCH3

glucose + acetyl chloride → glucose pentaacetate

Homework Equations



none

The Attempt at a Solution


I am thinking that the CH3COCl will split as CH3C+O and Cl-.
Now these positively charged group will react with the five OH groups by displacing the hydrogens.

But i am not understanding how there is bond between O-O in glucose pentaacetate (which doesn't fit in my above mechanism.)
 
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Discussion

This is just a limitation of linear representation of the structure. -OOC- does not mean a O-O bond, rather a carbon double bonded to an oxygen, and also singly bonded to a different oxygen.
 
I'd prefer nucleophilic attack on the acid chloride, rather than the acylium ion you have proposed.
 
can you explain why you are preferring the nucleophile attack?
 
I don't think the ion pair intermediate you've proposed is that stable, though I believe similar do exist in the presence of things like Fe or Al chlorides