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Mechanism of the formation of peracetic acid
Formation of peracetic acid from acetic acid and hydrogen peroxide and its stability in their presenceIs this the correct mechanism of the formation of the nitronium (NO2+) ion from sodium nitrate and sulfuric acid?Diethyl Ether reaction mechanism1-5 dicarboxylic acid to lactone with SOCl2?Mechanism of substitution reaction with no change in stereochemistryMechanism of Fisher esterification: Does the carboxylic acid gives off OH- or H+?Why does the proton transfer from the oxygen to the nitrogen atom in imine formation not occur through an intramolecular process?NGP mechanism vs the simple carbocation mechanismAcid Catalysed Ring Expansion – Mechanism?Role of solvents in ozonolysis and oz0nolysis of alkynes with waterWhy does Oxygen act as Nucleophile over here?
$begingroup$
Wikipedia says that the equilibrium $$ceH2O2 + CH3COOH ⇌ CH3COOOH + H2O$$ occurs. What is its mechanism?
The following is my speculation.
The first possibility is that $ceCH3COOH$ is protonated into $ceCH3CO(OH2)+$ because of the strong acid condition and then turns into $ceCH3C+O$. Because the oxygen atom in $ceH2O2$ is electron rich, it will bond with the carbon atom with positive charge to form $ceCH3C(=O)O(OH+)H$ and then peracetic acid is formed by deprotonation.
The second one is that the oxygen atom in $ceH2O2$ attacks the carbon atom in $ceMeCOOH$, then the $ceOH$ in $ceCOOH$ 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 Apr 24 at 3:37
Kemono ChenKemono Chen
1486
$endgroup$
add a comment |
$begingroup$
Wikipedia says that the equilibrium $$ceH2O2 + CH3COOH ⇌ CH3COOOH + H2O$$ occurs. What is its mechanism?
The following is my speculation.
The first possibility is that $ceCH3COOH$ is protonated into $ceCH3CO(OH2)+$ because of the strong acid condition and then turns into $ceCH3C+O$. Because the oxygen atom in $ceH2O2$ is electron rich, it will bond with the carbon atom with positive charge to form $ceCH3C(=O)O(OH+)H$ and then peracetic acid is formed by deprotonation.
The second one is that the oxygen atom in $ceH2O2$ attacks the carbon atom in $ceMeCOOH$, then the $ceOH$ in $ceCOOH$ 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 Apr 24 at 3:37
Kemono ChenKemono Chen
1486
$endgroup$
add a comment |
$begingroup$
Wikipedia says that the equilibrium $$ceH2O2 + CH3COOH ⇌ CH3COOOH + H2O$$ occurs. What is its mechanism?
The following is my speculation.
The first possibility is that $ceCH3COOH$ is protonated into $ceCH3CO(OH2)+$ because of the strong acid condition and then turns into $ceCH3C+O$. Because the oxygen atom in $ceH2O2$ is electron rich, it will bond with the carbon atom with positive charge to form $ceCH3C(=O)O(OH+)H$ and then peracetic acid is formed by deprotonation.
The second one is that the oxygen atom in $ceH2O2$ attacks the carbon atom in $ceMeCOOH$, then the $ceOH$ in $ceCOOH$ 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 Apr 24 at 3:37
Kemono ChenKemono Chen
1486
$endgroup$
Wikipedia says that the equilibrium $$ceH2O2 + CH3COOH ⇌ CH3COOOH + H2O$$ occurs. What is its mechanism?
The following is my speculation.
The first possibility is that $ceCH3COOH$ is protonated into $ceCH3CO(OH2)+$ because of the strong acid condition and then turns into $ceCH3C+O$. Because the oxygen atom in $ceH2O2$ is electron rich, it will bond with the carbon atom with positive charge to form $ceCH3C(=O)O(OH+)H$ and then peracetic acid is formed by deprotonation.
The second one is that the oxygen atom in $ceH2O2$ attacks the carbon atom in $ceMeCOOH$, then the $ceOH$ in $ceCOOH$ 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 Apr 24 at 3:37
Kemono ChenKemono Chen
1486
asked Apr 24 at 3:37
Kemono ChenKemono Chen
1486
asked Apr 24 at 3:37
Kemono ChenKemono Chen
1486
asked Apr 24 at 3:37
Kemono ChenKemono Chen
1486
asked Apr 24 at 3:37
Kemono ChenKemono Chen
1486
1486
add a comment |
add a comment |
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 Apr 24 at 4:28
ringoringo
20.3k559113
$endgroup$
add a comment |
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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 Apr 24 at 4:28
ringoringo
20.3k559113
$endgroup$
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 Apr 24 at 4:28
ringoringo
20.3k559113
$endgroup$
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 Apr 24 at 4:28
ringoringo
20.3k559113
$endgroup$
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 Apr 24 at 4:28
ringoringo
20.3k559113
answered Apr 24 at 4:28
ringoringo
20.3k559113
answered Apr 24 at 4:28
ringoringo
20.3k559113
answered Apr 24 at 4:28
ringoringo
20.3k559113
20.3k559113
add a comment |
add a comment |
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