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Reaction mechanism of rearrangement
Clarifications about the mechanism of the Wittig reactionSynthesis of phenoxyacetone from phenolHow to rationalise the major product formed in a nucleophile promoted epoxide cleavage reaction?Carbocation rearrangement with expansion of five-membered ring?Reduction of 1,4-benzoquinone in the synthesis of 1,5-diazocaneCarbocation Rearrangement in SNiIn what way could benzoin give Tollen's test?Elimination reaction with 1,2-dibromo-4-methylcyclohexaneDoes rearrangement occur in Friedel Crafts alkylation or not?Is 1,3 alkyl shift allowed in Cyclobutyldicyclopropylmethyl Cation?
$begingroup$
I am currently studying for my organic chemistry exam, but there is one problem I do not understand. Unfortunately, I do not have any solutions.
See image for the problem.
My first thought was the Dienone-phenol-rearrangement. But in order to do so, I need to add the alkyl substituent and I need a dienone. So can I deprotonate the phenol using potassium carbonate? (Or is it too weak as a base? The pKa of bicarbonate is around 10, so maybe it is too weak) But if it is possible, then the free electron pair of the oxygen can form a ketone... I could then use the alkene with a chloride substituent, so that the aromatic ring can attack it. Then I would have the dienone. But with the Dienone-phenol-rearrangement, the alkyl substituent can only move by one carbon-atom in the ring...
Is my thought process wrong? Can you please help me?
I did not have any lectures on rearrangement reactions, I had to learn them by myself, but by now, I have not found any similar reactions.
Thank you!
organic-chemistry reaction-mechanism rearrangements
asked 11 hours ago
QuestionCookieQuestionCookie
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QuestionCookie is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
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I am currently studying for my organic chemistry exam, but there is one problem I do not understand. Unfortunately, I do not have any solutions.
See image for the problem.
My first thought was the Dienone-phenol-rearrangement. But in order to do so, I need to add the alkyl substituent and I need a dienone. So can I deprotonate the phenol using potassium carbonate? (Or is it too weak as a base? The pKa of bicarbonate is around 10, so maybe it is too weak) But if it is possible, then the free electron pair of the oxygen can form a ketone... I could then use the alkene with a chloride substituent, so that the aromatic ring can attack it. Then I would have the dienone. But with the Dienone-phenol-rearrangement, the alkyl substituent can only move by one carbon-atom in the ring...
Is my thought process wrong? Can you please help me?
I did not have any lectures on rearrangement reactions, I had to learn them by myself, but by now, I have not found any similar reactions.
Thank you!
organic-chemistry reaction-mechanism rearrangements
asked 11 hours ago
QuestionCookieQuestionCookie
111 bronze badge
New contributor
QuestionCookie 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 |
$begingroup$
I am currently studying for my organic chemistry exam, but there is one problem I do not understand. Unfortunately, I do not have any solutions.
See image for the problem.
My first thought was the Dienone-phenol-rearrangement. But in order to do so, I need to add the alkyl substituent and I need a dienone. So can I deprotonate the phenol using potassium carbonate? (Or is it too weak as a base? The pKa of bicarbonate is around 10, so maybe it is too weak) But if it is possible, then the free electron pair of the oxygen can form a ketone... I could then use the alkene with a chloride substituent, so that the aromatic ring can attack it. Then I would have the dienone. But with the Dienone-phenol-rearrangement, the alkyl substituent can only move by one carbon-atom in the ring...
Is my thought process wrong? Can you please help me?
I did not have any lectures on rearrangement reactions, I had to learn them by myself, but by now, I have not found any similar reactions.
Thank you!
organic-chemistry reaction-mechanism rearrangements
asked 11 hours ago
QuestionCookieQuestionCookie
111 bronze badge
New contributor
QuestionCookie is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
$endgroup$
I am currently studying for my organic chemistry exam, but there is one problem I do not understand. Unfortunately, I do not have any solutions.
See image for the problem.
My first thought was the Dienone-phenol-rearrangement. But in order to do so, I need to add the alkyl substituent and I need a dienone. So can I deprotonate the phenol using potassium carbonate? (Or is it too weak as a base? The pKa of bicarbonate is around 10, so maybe it is too weak) But if it is possible, then the free electron pair of the oxygen can form a ketone... I could then use the alkene with a chloride substituent, so that the aromatic ring can attack it. Then I would have the dienone. But with the Dienone-phenol-rearrangement, the alkyl substituent can only move by one carbon-atom in the ring...
Is my thought process wrong? Can you please help me?
I did not have any lectures on rearrangement reactions, I had to learn them by myself, but by now, I have not found any similar reactions.
Thank you!
organic-chemistry reaction-mechanism rearrangements
organic-chemistry reaction-mechanism rearrangements
asked 11 hours ago
QuestionCookieQuestionCookie
111 bronze badge
New contributor
QuestionCookie is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
asked 11 hours ago
QuestionCookieQuestionCookie
111 bronze badge
New contributor
QuestionCookie is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
asked 11 hours ago
QuestionCookieQuestionCookie
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QuestionCookie is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
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asked 11 hours ago
QuestionCookieQuestionCookie
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asked 11 hours ago
QuestionCookieQuestionCookie
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QuestionCookie is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
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2 Answers
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Potassium carbonate is a perfectly good base for the alkylation of phenol (pKa 10) with a good electrophile, in this case 3,3-dimethylallylbromide. The reaction you are looking for is a Claisen rearrangement which proceeds by a 3,3-sigmatropic rearrangement mechanism.
image from ref 1
answered 11 hours ago
WaylanderWaylander
8,0621 gold badge18 silver badges28 bronze badges
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The first reaction is O-alkylation of p-cresol to give a 4-methylphenyl allyl ether derivative 3. The reagent in the first box should be 1-bromo-3-methylbut-2-ene (1; see the top box in the picture), which would undergo $mathrmS_N2$ reaction with phenolic anion (2) in refluxing acetone. Note that potassium carbonate is a strong enough base to complete this reaction (this is surely a strong base than potassium bicarbonate).
The product 3 from alkylation would undergo Claisen rearrangement upon heating to give final alkylated cresol 4 in solvent-free condition. Remember, Claisen found his famous rearrangement first in solvent-free conditions, while he was trying to find the melting point of newly synthesized naphthyl allyl ether! (Picture is from https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3873100/ and modified accordingly)
answered 1 hour ago
Mathew MahindaratneMathew Mahindaratne
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2 Answers
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2 Answers
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$begingroup$
Potassium carbonate is a perfectly good base for the alkylation of phenol (pKa 10) with a good electrophile, in this case 3,3-dimethylallylbromide. The reaction you are looking for is a Claisen rearrangement which proceeds by a 3,3-sigmatropic rearrangement mechanism.
image from ref 1
answered 11 hours ago
WaylanderWaylander
8,0621 gold badge18 silver badges28 bronze badges
$endgroup$
add a comment |
$begingroup$
Potassium carbonate is a perfectly good base for the alkylation of phenol (pKa 10) with a good electrophile, in this case 3,3-dimethylallylbromide. The reaction you are looking for is a Claisen rearrangement which proceeds by a 3,3-sigmatropic rearrangement mechanism.
image from ref 1
answered 11 hours ago
WaylanderWaylander
8,0621 gold badge18 silver badges28 bronze badges
$endgroup$
add a comment |
$begingroup$
Potassium carbonate is a perfectly good base for the alkylation of phenol (pKa 10) with a good electrophile, in this case 3,3-dimethylallylbromide. The reaction you are looking for is a Claisen rearrangement which proceeds by a 3,3-sigmatropic rearrangement mechanism.
image from ref 1
answered 11 hours ago
WaylanderWaylander
8,0621 gold badge18 silver badges28 bronze badges
$endgroup$
Potassium carbonate is a perfectly good base for the alkylation of phenol (pKa 10) with a good electrophile, in this case 3,3-dimethylallylbromide. The reaction you are looking for is a Claisen rearrangement which proceeds by a 3,3-sigmatropic rearrangement mechanism.
image from ref 1
answered 11 hours ago
WaylanderWaylander
8,0621 gold badge18 silver badges28 bronze badges
answered 11 hours ago
WaylanderWaylander
8,0621 gold badge18 silver badges28 bronze badges
answered 11 hours ago
WaylanderWaylander
8,0621 gold badge18 silver badges28 bronze badges
answered 11 hours ago
WaylanderWaylander
8,0621 gold badge18 silver badges28 bronze badges
8,0621 gold badge18 silver badges28 bronze badges
add a comment |
add a comment |
$begingroup$
The first reaction is O-alkylation of p-cresol to give a 4-methylphenyl allyl ether derivative 3. The reagent in the first box should be 1-bromo-3-methylbut-2-ene (1; see the top box in the picture), which would undergo $mathrmS_N2$ reaction with phenolic anion (2) in refluxing acetone. Note that potassium carbonate is a strong enough base to complete this reaction (this is surely a strong base than potassium bicarbonate).
The product 3 from alkylation would undergo Claisen rearrangement upon heating to give final alkylated cresol 4 in solvent-free condition. Remember, Claisen found his famous rearrangement first in solvent-free conditions, while he was trying to find the melting point of newly synthesized naphthyl allyl ether! (Picture is from https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3873100/ and modified accordingly)
answered 1 hour ago
Mathew MahindaratneMathew Mahindaratne
9,6651 gold badge11 silver badges34 bronze badges
$endgroup$
add a comment |
$begingroup$
The first reaction is O-alkylation of p-cresol to give a 4-methylphenyl allyl ether derivative 3. The reagent in the first box should be 1-bromo-3-methylbut-2-ene (1; see the top box in the picture), which would undergo $mathrmS_N2$ reaction with phenolic anion (2) in refluxing acetone. Note that potassium carbonate is a strong enough base to complete this reaction (this is surely a strong base than potassium bicarbonate).
The product 3 from alkylation would undergo Claisen rearrangement upon heating to give final alkylated cresol 4 in solvent-free condition. Remember, Claisen found his famous rearrangement first in solvent-free conditions, while he was trying to find the melting point of newly synthesized naphthyl allyl ether! (Picture is from https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3873100/ and modified accordingly)
answered 1 hour ago
Mathew MahindaratneMathew Mahindaratne
9,6651 gold badge11 silver badges34 bronze badges
$endgroup$
add a comment |
$begingroup$
The first reaction is O-alkylation of p-cresol to give a 4-methylphenyl allyl ether derivative 3. The reagent in the first box should be 1-bromo-3-methylbut-2-ene (1; see the top box in the picture), which would undergo $mathrmS_N2$ reaction with phenolic anion (2) in refluxing acetone. Note that potassium carbonate is a strong enough base to complete this reaction (this is surely a strong base than potassium bicarbonate).
The product 3 from alkylation would undergo Claisen rearrangement upon heating to give final alkylated cresol 4 in solvent-free condition. Remember, Claisen found his famous rearrangement first in solvent-free conditions, while he was trying to find the melting point of newly synthesized naphthyl allyl ether! (Picture is from https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3873100/ and modified accordingly)
answered 1 hour ago
Mathew MahindaratneMathew Mahindaratne
9,6651 gold badge11 silver badges34 bronze badges
$endgroup$
The first reaction is O-alkylation of p-cresol to give a 4-methylphenyl allyl ether derivative 3. The reagent in the first box should be 1-bromo-3-methylbut-2-ene (1; see the top box in the picture), which would undergo $mathrmS_N2$ reaction with phenolic anion (2) in refluxing acetone. Note that potassium carbonate is a strong enough base to complete this reaction (this is surely a strong base than potassium bicarbonate).
The product 3 from alkylation would undergo Claisen rearrangement upon heating to give final alkylated cresol 4 in solvent-free condition. Remember, Claisen found his famous rearrangement first in solvent-free conditions, while he was trying to find the melting point of newly synthesized naphthyl allyl ether! (Picture is from https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3873100/ and modified accordingly)
answered 1 hour ago
Mathew MahindaratneMathew Mahindaratne
9,6651 gold badge11 silver badges34 bronze badges
answered 1 hour ago
Mathew MahindaratneMathew Mahindaratne
9,6651 gold badge11 silver badges34 bronze badges
answered 1 hour ago
Mathew MahindaratneMathew Mahindaratne
9,6651 gold badge11 silver badges34 bronze badges
answered 1 hour ago
Mathew MahindaratneMathew Mahindaratne
9,6651 gold badge11 silver badges34 bronze badges
9,6651 gold badge11 silver badges34 bronze badges
add a comment |
add a comment |
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