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Acetone on treatment with magnesium amalgam gives a diol which rearranges in presence of acid to a ketone. Identify the ketone and represent the experiment with chemical equations and necessary mechanism.?
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Acetone on treatment with magnesium amalgam gives a diol which rearran...
Introduction
Acetone is a commonly used solvent in laboratories and industries. When treated with magnesium amalgam, it gives a diol which upon rearrangement in the presence of acid yields a ketone.
Chemical Equations
The reaction of acetone with magnesium amalgam can be represented as follows:
CH3COCH3 + Mg/Hg → CH3C(OH)(OH)CH3
The above reaction yields a diol, which upon treatment with acid undergoes a rearrangement reaction to yield a ketone. The mechanism of this rearrangement reaction is as follows:
Mechanism of Rearrangement Reaction
The rearrangement reaction of the diol formed in the above reaction can be explained by the following mechanism:
1. Protonation: The diol is protonated by the acid, forming an oxonium ion.
CH3C(OH)(OH)CH3 + H+ → CH3C(OH)2CH3+
2. Migration: The oxygen atom of the hydroxyl group adjacent to the carbonyl group migrates to the carbonyl carbon, forming a transition state.
CH3C(OH)2CH3+ → CH3C(=O)CH3OH2+
3. Deprotonation: The oxonium ion loses a proton, forming the final product, a ketone.
CH3C(=O)CH3OH2+ → CH3C(=O)CH3 + H2O
Identification of Ketone
The ketone formed in the above reaction is mesityl oxide, which has a chemical formula of C6H10O. The structure of mesityl oxide is as follows:
CH3
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CH3C=O
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CH3
Conclusion
Acetone on treatment with magnesium amalgam gives a diol, which upon rearrangement in the presence of acid yields mesityl oxide, a ketone. The rearrangement reaction occurs through a mechanism involving protonation, migration, and deprotonation.
Acetone is a commonly used solvent in laboratories and industries. When treated with magnesium amalgam, it gives a diol which upon rearrangement in the presence of acid yields a ketone.
Chemical Equations
The reaction of acetone with magnesium amalgam can be represented as follows:
CH3COCH3 + Mg/Hg → CH3C(OH)(OH)CH3
The above reaction yields a diol, which upon treatment with acid undergoes a rearrangement reaction to yield a ketone. The mechanism of this rearrangement reaction is as follows:
Mechanism of Rearrangement Reaction
The rearrangement reaction of the diol formed in the above reaction can be explained by the following mechanism:
1. Protonation: The diol is protonated by the acid, forming an oxonium ion.
CH3C(OH)(OH)CH3 + H+ → CH3C(OH)2CH3+
2. Migration: The oxygen atom of the hydroxyl group adjacent to the carbonyl group migrates to the carbonyl carbon, forming a transition state.
CH3C(OH)2CH3+ → CH3C(=O)CH3OH2+
3. Deprotonation: The oxonium ion loses a proton, forming the final product, a ketone.
CH3C(=O)CH3OH2+ → CH3C(=O)CH3 + H2O
Identification of Ketone
The ketone formed in the above reaction is mesityl oxide, which has a chemical formula of C6H10O. The structure of mesityl oxide is as follows:
CH3
|
CH3C=O
|
CH3
Conclusion
Acetone on treatment with magnesium amalgam gives a diol, which upon rearrangement in the presence of acid yields mesityl oxide, a ketone. The rearrangement reaction occurs through a mechanism involving protonation, migration, and deprotonation.
Community Answer
Acetone on treatment with magnesium amalgam gives a diol which rearran...
Acetone--->pinacol
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Acetone on treatment with magnesium amalgam gives a diol which rearranges in presence of acid to a ketone. Identify the ketone and represent the experiment with chemical equations and necessary mechanism.?
Question Description
Acetone on treatment with magnesium amalgam gives a diol which rearranges in presence of acid to a ketone. Identify the ketone and represent the experiment with chemical equations and necessary mechanism.? for IIT JAM 2024 is part of IIT JAM preparation. The Question and answers have been prepared according to the IIT JAM exam syllabus. Information about Acetone on treatment with magnesium amalgam gives a diol which rearranges in presence of acid to a ketone. Identify the ketone and represent the experiment with chemical equations and necessary mechanism.? covers all topics & solutions for IIT JAM 2024 Exam. Find important definitions, questions, meanings, examples, exercises and tests below for Acetone on treatment with magnesium amalgam gives a diol which rearranges in presence of acid to a ketone. Identify the ketone and represent the experiment with chemical equations and necessary mechanism.?.
Acetone on treatment with magnesium amalgam gives a diol which rearranges in presence of acid to a ketone. Identify the ketone and represent the experiment with chemical equations and necessary mechanism.? for IIT JAM 2024 is part of IIT JAM preparation. The Question and answers have been prepared according to the IIT JAM exam syllabus. Information about Acetone on treatment with magnesium amalgam gives a diol which rearranges in presence of acid to a ketone. Identify the ketone and represent the experiment with chemical equations and necessary mechanism.? covers all topics & solutions for IIT JAM 2024 Exam. Find important definitions, questions, meanings, examples, exercises and tests below for Acetone on treatment with magnesium amalgam gives a diol which rearranges in presence of acid to a ketone. Identify the ketone and represent the experiment with chemical equations and necessary mechanism.?.
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