Mechanism of the formation of peracetic acid Unicorn Meta Zoo #1: Why another podcast? ...

Mechanism of the formation of peracetic acid

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Mechanism of the formation of peracetic acid



Unicorn Meta Zoo #1: Why another podcast?
Announcing the arrival of Valued Associate #679: Cesar Manara
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2












$begingroup$


Wikipedia says that the equilibrium $$ce{H2O2 + CH3COOH ⇌ CH3COOOH + H2O}$$ occurs. What is its mechanism?

The following is my speculation.



The first possibility is that $ce{CH3COOH}$ is protonated into $ce{CH3CO(OH2)+}$ because of the strong acid condition and then turns into $ce{CH3C+O}$. Because the oxygen atom in $ce{H2O2}$ is electron rich, it will bond with the carbon atom with positive charge to form $ce{CH3C(=O)O(OH+)H}$ and then peracetic acid is formed by deprotonation.

The second one is that the oxygen atom in $ce{H2O2}$ attacks the carbon atom in $ce{MeCOOH}$, then the $ce{OH}$ in $ce{COOH}$ and
one of the $ce H$ in $ce {H2O2}$ leave.



Is the mechanism above right or not? If it is not, what's the correct one?



P.S. (this question does not answer my question)










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    2












    $begingroup$


    Wikipedia says that the equilibrium $$ce{H2O2 + CH3COOH ⇌ CH3COOOH + H2O}$$ occurs. What is its mechanism?

    The following is my speculation.



    The first possibility is that $ce{CH3COOH}$ is protonated into $ce{CH3CO(OH2)+}$ because of the strong acid condition and then turns into $ce{CH3C+O}$. Because the oxygen atom in $ce{H2O2}$ is electron rich, it will bond with the carbon atom with positive charge to form $ce{CH3C(=O)O(OH+)H}$ and then peracetic acid is formed by deprotonation.

    The second one is that the oxygen atom in $ce{H2O2}$ attacks the carbon atom in $ce{MeCOOH}$, then the $ce{OH}$ in $ce{COOH}$ and
    one of the $ce H$ in $ce {H2O2}$ leave.



    Is the mechanism above right or not? If it is not, what's the correct one?



    P.S. (this question does not answer my question)










    share|improve this question







    New contributor




    Kemono Chen is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
    Check out our Code of Conduct.







    $endgroup$















      2












      2








      2





      $begingroup$


      Wikipedia says that the equilibrium $$ce{H2O2 + CH3COOH ⇌ CH3COOOH + H2O}$$ occurs. What is its mechanism?

      The following is my speculation.



      The first possibility is that $ce{CH3COOH}$ is protonated into $ce{CH3CO(OH2)+}$ because of the strong acid condition and then turns into $ce{CH3C+O}$. Because the oxygen atom in $ce{H2O2}$ is electron rich, it will bond with the carbon atom with positive charge to form $ce{CH3C(=O)O(OH+)H}$ and then peracetic acid is formed by deprotonation.

      The second one is that the oxygen atom in $ce{H2O2}$ attacks the carbon atom in $ce{MeCOOH}$, then the $ce{OH}$ in $ce{COOH}$ and
      one of the $ce H$ in $ce {H2O2}$ leave.



      Is the mechanism above right or not? If it is not, what's the correct one?



      P.S. (this question does not answer my question)










      share|improve this question







      New contributor




      Kemono Chen is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
      Check out our Code of Conduct.







      $endgroup$




      Wikipedia says that the equilibrium $$ce{H2O2 + CH3COOH ⇌ CH3COOOH + H2O}$$ occurs. What is its mechanism?

      The following is my speculation.



      The first possibility is that $ce{CH3COOH}$ is protonated into $ce{CH3CO(OH2)+}$ because of the strong acid condition and then turns into $ce{CH3C+O}$. Because the oxygen atom in $ce{H2O2}$ is electron rich, it will bond with the carbon atom with positive charge to form $ce{CH3C(=O)O(OH+)H}$ and then peracetic acid is formed by deprotonation.

      The second one is that the oxygen atom in $ce{H2O2}$ attacks the carbon atom in $ce{MeCOOH}$, then the $ce{OH}$ in $ce{COOH}$ and
      one of the $ce H$ in $ce {H2O2}$ leave.



      Is the mechanism above right or not? If it is not, what's the correct one?



      P.S. (this question does not answer my question)







      organic-chemistry reaction-mechanism






      share|improve this question







      New contributor




      Kemono Chen is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
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      share|improve this question






      New contributor




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      asked 1 hour ago









      Kemono ChenKemono Chen

      1134




      1134




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          $begingroup$

          You are not too far off. It is somewhat of a mixture of the two mechanisms you proposed. The carbonyl oxygen is much more basic than the non-carbonyl oxygen and will be protonated preferentially. Then hydrogen peroxide can attack, and once the tetrahedral intermediate collapses, deprotonation yields peracetic acid.



          enter image description here






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            $begingroup$

            You are not too far off. It is somewhat of a mixture of the two mechanisms you proposed. The carbonyl oxygen is much more basic than the non-carbonyl oxygen and will be protonated preferentially. Then hydrogen peroxide can attack, and once the tetrahedral intermediate collapses, deprotonation yields peracetic acid.



            enter image description here






            share|improve this answer









            $endgroup$


















              2












              $begingroup$

              You are not too far off. It is somewhat of a mixture of the two mechanisms you proposed. The carbonyl oxygen is much more basic than the non-carbonyl oxygen and will be protonated preferentially. Then hydrogen peroxide can attack, and once the tetrahedral intermediate collapses, deprotonation yields peracetic acid.



              enter image description here






              share|improve this answer









              $endgroup$
















                2












                2








                2





                $begingroup$

                You are not too far off. It is somewhat of a mixture of the two mechanisms you proposed. The carbonyl oxygen is much more basic than the non-carbonyl oxygen and will be protonated preferentially. Then hydrogen peroxide can attack, and once the tetrahedral intermediate collapses, deprotonation yields peracetic acid.



                enter image description here






                share|improve this answer









                $endgroup$



                You are not too far off. It is somewhat of a mixture of the two mechanisms you proposed. The carbonyl oxygen is much more basic than the non-carbonyl oxygen and will be protonated preferentially. Then hydrogen peroxide can attack, and once the tetrahedral intermediate collapses, deprotonation yields peracetic acid.



                enter image description here







                share|improve this answer












                share|improve this answer



                share|improve this answer










                answered 45 mins ago









                ringoringo

                20.3k559112




                20.3k559112






















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