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Mechanism of reaction

  1. Jul 6, 2013 #1
    1. The problem statement, all variables and given/known data

    can anybody explain the mechanism of the reaction



    C6H12O6 +CH3COCl → CHO(CHOOCCH3)4CH2OOCCH3

    glucose + acetyl chloride → glucose pentaacetate

    2. Relevant equations

    none

    3. 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.)
     
  2. jcsd
  3. Jul 6, 2013 #2
    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.
     
  4. Jul 6, 2013 #3
    Then is the mechanism correct?
     
  5. Jul 7, 2013 #4
    I'd prefer nucleophilic attack on the acid chloride, rather than the acylium ion you have proposed.
     
  6. Jul 7, 2013 #5
    can you explain why you are preferring the nucleophile attack?
     
  7. Jul 7, 2013 #6
    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
     
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