Mechanism of Acid HydrolysisAcid-catalyzed hydrolysis of diphenyl malonateAcid catalyzed hydrolysis of esterAlkaline Ester Hydrolysis Reactionselective hydrolysis problemHydrolysis of an esterWeak acid and weak base salt hydrolysisWhich mechanism is not seen during hydrolysis of esters?Acid hydrolysis of ethyl acetateAcid hydrolysis of ethyl acetate usesHydrolysis under basic medium
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Extracting data from Plot
Mechanism of Acid Hydrolysis
Acid-catalyzed hydrolysis of diphenyl malonateAcid catalyzed hydrolysis of esterAlkaline Ester Hydrolysis Reactionselective hydrolysis problemHydrolysis of an esterWeak acid and weak base salt hydrolysisWhich mechanism is not seen during hydrolysis of esters?Acid hydrolysis of ethyl acetateAcid hydrolysis of ethyl acetate usesHydrolysis under basic medium
$begingroup$
I wanted to ask a question about acid catalysed hydrolysis.
I learnt in an introductory course to Physical Organic Chemistry that there are different ways that an ester can be hydrolysed acidically:
$ceA_AC1$
$ceA_AC2$
$ceA_AL1$
$ceA_AL2$
There are different ways that esters can be hydrolysed:
– catalysis by acids (A) or bases (B)
– cleavage of acyl-oxy (AC) or alkyl-oxy (AL) bonds
– the molecularity of the key step (1 or 2).
Using Acids (A) there are 4 different ways to hydrolyse an ester using acid catalysis:
$ceA_AC1$ Cleavage of Acyl-Oxy Bond Unimolecular
$ceA_AC2$ Cleavage of Acyl-Oxy Bond Dimolecular
$ceA_AL1$ Cleavage of Alkyl-Oxy Bond Unimolecular
$ceA_AL2$ Cleavage of Alkyl-Oxy Bond Dimolecular
An explanation can be found here.
But consider this question, with the marking scheme given below:
Our professor did not mention anything regarding how to choose which type of hydrolysis takes place. From this question, he states and goes further onto mention that either $ceA_AC1$ or $ceA_AC2$ can take place, but no other.
I'm looking at these structures and thinking
Why can't $ceA_AL1$ or $ceA_AL2$ take place for these two? Why must it be the two given in them marking scheme?
hydrolysis esters
asked 8 hours ago
vik1245vik1245
347115
$endgroup$
add a comment |
$begingroup$
I wanted to ask a question about acid catalysed hydrolysis.
I learnt in an introductory course to Physical Organic Chemistry that there are different ways that an ester can be hydrolysed acidically:
$ceA_AC1$
$ceA_AC2$
$ceA_AL1$
$ceA_AL2$
There are different ways that esters can be hydrolysed:
– catalysis by acids (A) or bases (B)
– cleavage of acyl-oxy (AC) or alkyl-oxy (AL) bonds
– the molecularity of the key step (1 or 2).
Using Acids (A) there are 4 different ways to hydrolyse an ester using acid catalysis:
$ceA_AC1$ Cleavage of Acyl-Oxy Bond Unimolecular
$ceA_AC2$ Cleavage of Acyl-Oxy Bond Dimolecular
$ceA_AL1$ Cleavage of Alkyl-Oxy Bond Unimolecular
$ceA_AL2$ Cleavage of Alkyl-Oxy Bond Dimolecular
An explanation can be found here.
But consider this question, with the marking scheme given below:
Our professor did not mention anything regarding how to choose which type of hydrolysis takes place. From this question, he states and goes further onto mention that either $ceA_AC1$ or $ceA_AC2$ can take place, but no other.
I'm looking at these structures and thinking
Why can't $ceA_AL1$ or $ceA_AL2$ take place for these two? Why must it be the two given in them marking scheme?
hydrolysis esters
asked 8 hours ago
vik1245vik1245
347115
$endgroup$
1
$begingroup$
Perhaps you could explain in a few words what those mechanisms mean, or provide a reference. I think that's not too widely known.
$endgroup$
– Karl
8 hours ago
$begingroup$
@Karl Edit made. Reference added.
$endgroup$
– vik1245
8 hours ago
2
$begingroup$
+1 , but I wouldn't add this as a P.S. People have a short attention span, they read five lines, find they don't get it, and move on. ;-)
$endgroup$
– Karl
7 hours ago
$begingroup$
@Karl edited it further so now it appears in the introduction rather than the end!
$endgroup$
– vik1245
7 hours ago
add a comment |
$begingroup$
I wanted to ask a question about acid catalysed hydrolysis.
I learnt in an introductory course to Physical Organic Chemistry that there are different ways that an ester can be hydrolysed acidically:
$ceA_AC1$
$ceA_AC2$
$ceA_AL1$
$ceA_AL2$
There are different ways that esters can be hydrolysed:
– catalysis by acids (A) or bases (B)
– cleavage of acyl-oxy (AC) or alkyl-oxy (AL) bonds
– the molecularity of the key step (1 or 2).
Using Acids (A) there are 4 different ways to hydrolyse an ester using acid catalysis:
$ceA_AC1$ Cleavage of Acyl-Oxy Bond Unimolecular
$ceA_AC2$ Cleavage of Acyl-Oxy Bond Dimolecular
$ceA_AL1$ Cleavage of Alkyl-Oxy Bond Unimolecular
$ceA_AL2$ Cleavage of Alkyl-Oxy Bond Dimolecular
An explanation can be found here.
But consider this question, with the marking scheme given below:
Our professor did not mention anything regarding how to choose which type of hydrolysis takes place. From this question, he states and goes further onto mention that either $ceA_AC1$ or $ceA_AC2$ can take place, but no other.
I'm looking at these structures and thinking
Why can't $ceA_AL1$ or $ceA_AL2$ take place for these two? Why must it be the two given in them marking scheme?
hydrolysis esters
asked 8 hours ago
vik1245vik1245
347115
$endgroup$
I wanted to ask a question about acid catalysed hydrolysis.
I learnt in an introductory course to Physical Organic Chemistry that there are different ways that an ester can be hydrolysed acidically:
$ceA_AC1$
$ceA_AC2$
$ceA_AL1$
$ceA_AL2$
There are different ways that esters can be hydrolysed:
– catalysis by acids (A) or bases (B)
– cleavage of acyl-oxy (AC) or alkyl-oxy (AL) bonds
– the molecularity of the key step (1 or 2).
Using Acids (A) there are 4 different ways to hydrolyse an ester using acid catalysis:
$ceA_AC1$ Cleavage of Acyl-Oxy Bond Unimolecular
$ceA_AC2$ Cleavage of Acyl-Oxy Bond Dimolecular
$ceA_AL1$ Cleavage of Alkyl-Oxy Bond Unimolecular
$ceA_AL2$ Cleavage of Alkyl-Oxy Bond Dimolecular
An explanation can be found here.
But consider this question, with the marking scheme given below:
Our professor did not mention anything regarding how to choose which type of hydrolysis takes place. From this question, he states and goes further onto mention that either $ceA_AC1$ or $ceA_AC2$ can take place, but no other.
I'm looking at these structures and thinking
Why can't $ceA_AL1$ or $ceA_AL2$ take place for these two? Why must it be the two given in them marking scheme?
hydrolysis esters
hydrolysis esters
asked 8 hours ago
vik1245vik1245
347115
asked 8 hours ago
vik1245vik1245
347115
edited 7 hours ago
vik1245
asked 8 hours ago
vik1245vik1245
347115
asked 8 hours ago
vik1245vik1245
347115
asked 8 hours ago
vik1245vik1245
347115
347115
1
$begingroup$
Perhaps you could explain in a few words what those mechanisms mean, or provide a reference. I think that's not too widely known.
$endgroup$
– Karl
8 hours ago
$begingroup$
@Karl Edit made. Reference added.
$endgroup$
– vik1245
8 hours ago
2
$begingroup$
+1 , but I wouldn't add this as a P.S. People have a short attention span, they read five lines, find they don't get it, and move on. ;-)
$endgroup$
– Karl
7 hours ago
$begingroup$
@Karl edited it further so now it appears in the introduction rather than the end!
$endgroup$
– vik1245
7 hours ago
add a comment |
1
$begingroup$
Perhaps you could explain in a few words what those mechanisms mean, or provide a reference. I think that's not too widely known.
$endgroup$
– Karl
8 hours ago
$begingroup$
@Karl Edit made. Reference added.
$endgroup$
– vik1245
8 hours ago
2
$begingroup$
+1 , but I wouldn't add this as a P.S. People have a short attention span, they read five lines, find they don't get it, and move on. ;-)
$endgroup$
– Karl
7 hours ago
$begingroup$
@Karl edited it further so now it appears in the introduction rather than the end!
$endgroup$
– vik1245
7 hours ago
1
1
$begingroup$
Perhaps you could explain in a few words what those mechanisms mean, or provide a reference. I think that's not too widely known.
$endgroup$
– Karl
8 hours ago
$begingroup$
Perhaps you could explain in a few words what those mechanisms mean, or provide a reference. I think that's not too widely known.
$endgroup$
– Karl
8 hours ago
$begingroup$
@Karl Edit made. Reference added.
$endgroup$
– vik1245
8 hours ago
$begingroup$
@Karl Edit made. Reference added.
$endgroup$
– vik1245
8 hours ago
2
2
$begingroup$
+1 , but I wouldn't add this as a P.S. People have a short attention span, they read five lines, find they don't get it, and move on. ;-)
$endgroup$
– Karl
7 hours ago
$begingroup$
+1 , but I wouldn't add this as a P.S. People have a short attention span, they read five lines, find they don't get it, and move on. ;-)
$endgroup$
– Karl
7 hours ago
$begingroup$
@Karl edited it further so now it appears in the introduction rather than the end!
$endgroup$
– vik1245
7 hours ago
$begingroup$
@Karl edited it further so now it appears in the introduction rather than the end!
$endgroup$
– vik1245
7 hours ago
add a comment |
1 Answer
1
active
oldest
votes
$begingroup$
You should have read your explanation material more carefully! It clearly states that $A_AL2$ has not even been observed in acid hydrolysis due to water being a poor nucleophile in an $S_N2$ process. As for $A_AL1$, that only happens when the esterified radical can leave as a stable carbocation which, in this case methyl is a very very unstable carbocation.
answered 7 hours ago
Valentin LupuValentin Lupu
662
New contributor
Valentin Lupu is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
$endgroup$
$begingroup$
Well if I am such a fool then I will learn today! Thanks very much this isn't actually my material but I read it so fast I couldn't actually make the point clear to myself! My apologies!
$endgroup$
– vik1245
7 hours ago
add a comment |
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1 Answer
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1 Answer
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$begingroup$
You should have read your explanation material more carefully! It clearly states that $A_AL2$ has not even been observed in acid hydrolysis due to water being a poor nucleophile in an $S_N2$ process. As for $A_AL1$, that only happens when the esterified radical can leave as a stable carbocation which, in this case methyl is a very very unstable carbocation.
answered 7 hours ago
Valentin LupuValentin Lupu
662
New contributor
Valentin Lupu is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
$endgroup$
$begingroup$
Well if I am such a fool then I will learn today! Thanks very much this isn't actually my material but I read it so fast I couldn't actually make the point clear to myself! My apologies!
$endgroup$
– vik1245
7 hours ago
add a comment |
$begingroup$
You should have read your explanation material more carefully! It clearly states that $A_AL2$ has not even been observed in acid hydrolysis due to water being a poor nucleophile in an $S_N2$ process. As for $A_AL1$, that only happens when the esterified radical can leave as a stable carbocation which, in this case methyl is a very very unstable carbocation.
answered 7 hours ago
Valentin LupuValentin Lupu
662
New contributor
Valentin Lupu is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
$endgroup$
$begingroup$
Well if I am such a fool then I will learn today! Thanks very much this isn't actually my material but I read it so fast I couldn't actually make the point clear to myself! My apologies!
$endgroup$
– vik1245
7 hours ago
add a comment |
$begingroup$
You should have read your explanation material more carefully! It clearly states that $A_AL2$ has not even been observed in acid hydrolysis due to water being a poor nucleophile in an $S_N2$ process. As for $A_AL1$, that only happens when the esterified radical can leave as a stable carbocation which, in this case methyl is a very very unstable carbocation.
answered 7 hours ago
Valentin LupuValentin Lupu
662
New contributor
Valentin Lupu is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
$endgroup$
You should have read your explanation material more carefully! It clearly states that $A_AL2$ has not even been observed in acid hydrolysis due to water being a poor nucleophile in an $S_N2$ process. As for $A_AL1$, that only happens when the esterified radical can leave as a stable carbocation which, in this case methyl is a very very unstable carbocation.
answered 7 hours ago
Valentin LupuValentin Lupu
662
New contributor
Valentin Lupu is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
answered 7 hours ago
Valentin LupuValentin Lupu
662
New contributor
Valentin Lupu is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
answered 7 hours ago
Valentin LupuValentin Lupu
662
answered 7 hours ago
Valentin LupuValentin Lupu
662
662
New contributor
Valentin Lupu is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
New contributor
Valentin Lupu is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
$begingroup$
Well if I am such a fool then I will learn today! Thanks very much this isn't actually my material but I read it so fast I couldn't actually make the point clear to myself! My apologies!
$endgroup$
– vik1245
7 hours ago
add a comment |
$begingroup$
Well if I am such a fool then I will learn today! Thanks very much this isn't actually my material but I read it so fast I couldn't actually make the point clear to myself! My apologies!
$endgroup$
– vik1245
7 hours ago
$begingroup$
Well if I am such a fool then I will learn today! Thanks very much this isn't actually my material but I read it so fast I couldn't actually make the point clear to myself! My apologies!
$endgroup$
– vik1245
7 hours ago
$begingroup$
Well if I am such a fool then I will learn today! Thanks very much this isn't actually my material but I read it so fast I couldn't actually make the point clear to myself! My apologies!
$endgroup$
– vik1245
7 hours ago
add a comment |
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1
$begingroup$
Perhaps you could explain in a few words what those mechanisms mean, or provide a reference. I think that's not too widely known.
$endgroup$
– Karl
8 hours ago
$begingroup$
@Karl Edit made. Reference added.
$endgroup$
– vik1245
8 hours ago
2
$begingroup$
+1 , but I wouldn't add this as a P.S. People have a short attention span, they read five lines, find they don't get it, and move on. ;-)
$endgroup$
– Karl
7 hours ago
$begingroup$
@Karl edited it further so now it appears in the introduction rather than the end!
$endgroup$
– vik1245
7 hours ago