Mechanism of the formation of peracetic acid
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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
asked 2 hours ago
Kemono ChenKemono Chen
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$begingroup$
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)
organic-chemistry reaction-mechanism
asked 2 hours ago
Kemono ChenKemono Chen
1134
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.
$endgroup$
add a comment |
$begingroup$
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)
organic-chemistry reaction-mechanism
asked 2 hours ago
Kemono ChenKemono Chen
1134
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
organic-chemistry reaction-mechanism
asked 2 hours ago
Kemono ChenKemono Chen
1134
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.
asked 2 hours ago
Kemono ChenKemono Chen
1134
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.
asked 2 hours ago
Kemono ChenKemono Chen
1134
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.
asked 2 hours ago
Kemono ChenKemono Chen
1134
asked 2 hours ago
Kemono ChenKemono Chen
1134
1134
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.
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.
Kemono Chen is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
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1 Answer
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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.
answered 1 hour ago
ringoringo
20.3k559112
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1 Answer
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1 Answer
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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.
answered 1 hour ago
ringoringo
20.3k559112
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add a comment |
$begingroup$
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.
answered 1 hour ago
ringoringo
20.3k559112
$endgroup$
add a comment |
$begingroup$
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.
answered 1 hour ago
ringoringo
20.3k559112
$endgroup$
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.
answered 1 hour ago
ringoringo
20.3k559112
answered 1 hour ago
ringoringo
20.3k559112
answered 1 hour ago
ringoringo
20.3k559112
answered 1 hour ago
ringoringo
20.3k559112
20.3k559112
add a comment |
add a comment |
Kemono Chen is a new contributor. Be nice, and check out our Code of Conduct.
Kemono Chen is a new contributor. Be nice, and check out our Code of Conduct.
Kemono Chen is a new contributor. Be nice, and check out our Code of Conduct.
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