Explaining Mechanism of Glucose Pentaacetate Reaction

In summary, the conversation discusses the mechanism of a reaction between glucose and acetyl chloride, resulting in the formation of glucose pentaacetate. The proposed mechanism involves the splitting of CH3COCl into CH3C+O and Cl-, with the positively charged group reacting with the OH groups in glucose. However, there is confusion about the bond between O-O in glucose pentaacetate and whether the proposed mechanism is correct. One person suggests a nucleophilic attack on the acid chloride, while another questions the stability of the proposed ion pair intermediate.
  • #1
nil1996
301
7

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

1. What is the mechanism of the glucose pentaacetate reaction?

The mechanism of the glucose pentaacetate reaction involves the conversion of glucose into glucose pentaacetate through a series of chemical reactions. The first step is the formation of an intermediate compound, glucose pentaacetate hemiacetal, which then undergoes acetylation to form the final product, glucose pentaacetate.

2. What is the purpose of using glucose pentaacetate in reactions?

The purpose of using glucose pentaacetate in reactions is to increase the reactivity of glucose. The acetyl groups attached to the glucose molecule make it more susceptible to chemical reactions, thereby allowing for the synthesis of various compounds.

3. How does the reaction occur at a molecular level?

At a molecular level, the glucose pentaacetate reaction involves the cleavage of the glycosidic bond in glucose, followed by the addition of acetyl groups to the resulting molecules. This process occurs in the presence of an acid catalyst and an acetylating agent, such as acetic anhydride.

4. What factors influence the rate of the glucose pentaacetate reaction?

The rate of the glucose pentaacetate reaction can be influenced by several factors, including the concentration of the reactants, the temperature, and the presence of a catalyst. Higher concentrations and temperatures generally increase the rate of the reaction, while a catalyst can speed up the reaction by lowering the activation energy.

5. What are the potential products of the glucose pentaacetate reaction?

The potential products of the glucose pentaacetate reaction depend on the specific reagents and conditions used. In addition to glucose pentaacetate, other possible products include acetylated derivatives of glucose, such as glucose tetraacetate and glucose hexaacetate. The final product may also vary depending on the degree of acetylation and the presence of any impurities in the reactants.

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