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Reaction mechanism of rearrangement
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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 8 hours ago
QuestionCookieQuestionCookie
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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 8 hours ago
QuestionCookieQuestionCookie
61 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 8 hours ago
QuestionCookieQuestionCookie
61 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 8 hours ago
QuestionCookieQuestionCookie
61 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 8 hours ago
QuestionCookieQuestionCookie
61 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 8 hours ago
QuestionCookieQuestionCookie
61 bronze badge
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QuestionCookie is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
asked 8 hours ago
QuestionCookieQuestionCookie
61 bronze badge
asked 8 hours ago
QuestionCookieQuestionCookie
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61 bronze badge
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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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1 Answer
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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 8 hours ago
WaylanderWaylander
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1 Answer
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1 Answer
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active
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votes
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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 8 hours ago
WaylanderWaylander
8,0321 gold badge18 silver badges28 bronze badges
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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 8 hours ago
WaylanderWaylander
8,0321 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 8 hours ago
WaylanderWaylander
8,0321 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 8 hours ago
WaylanderWaylander
8,0321 gold badge18 silver badges28 bronze badges
answered 8 hours ago
WaylanderWaylander
8,0321 gold badge18 silver badges28 bronze badges
answered 8 hours ago
WaylanderWaylander
8,0321 gold badge18 silver badges28 bronze badges
answered 8 hours ago
WaylanderWaylander
8,0321 gold badge18 silver badges28 bronze badges
8,0321 gold badge18 silver badges28 bronze badges
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