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On heating in the presence of bromine, 2, 2-dimethyl-3-oxobutyric acid produces 3-bromo-3-methyl-2-butanone. What unstable intermediate is involved in this reaction?
  • a)
    1,2, 2-trimethyicyclopropanol
  • b)
    2, 2-dimethyl β-butyrolactone
  • c)
    2-hydroxy-3-methylbutene
  • d)
    dimethylketene
Correct answer is option 'C'. Can you explain this answer?
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On heating in the presence of bromine, 2, 2-dimethyl-3-oxobutyric acid...
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On heating in the presence of bromine, 2, 2-dimethyl-3-oxobutyric acid...
2, 2-dimethyl-3-oxobutyric acid undergoes a reaction with bromine in the presence of heat to produce 3-bromo-3-methyl-2-butanone. This reaction involves the formation of an unstable intermediate, which is 2-hydroxy-3-methylbutene.

Explanation:

1. Reaction Overview:
- The reaction involves the addition of bromine to the double bond present in 2, 2-dimethyl-3-oxobutyric acid.
- This addition reaction leads to the formation of an unstable intermediate, which further undergoes a rearrangement to give the final product, 3-bromo-3-methyl-2-butanone.
- The mechanism of this reaction proceeds through the formation of a carbocation intermediate, which is subsequently attacked by bromine.

2. Formation of the Unstable Intermediate:
- The initial step of the reaction involves the addition of bromine to the double bond present in 2, 2-dimethyl-3-oxobutyric acid.
- This addition leads to the formation of a bromonium ion intermediate, which is a cyclic structure with a positive charge on one of the bromine atoms and a partial positive charge on the other bromine atom.
- The bromonium ion intermediate is highly unstable due to the positive charge on one of the bromine atoms, and it undergoes a rearrangement to stabilize itself.

3. Rearrangement to Stabilize the Intermediate:
- The unstable bromonium ion intermediate undergoes a rearrangement to stabilize itself and form a more stable intermediate.
- This rearrangement involves the migration of a hydrogen atom from the methyl group adjacent to the carbonyl group to the carbon atom bearing the positive charge.
- The resulting intermediate is 2-hydroxy-3-methylbutene, which is stabilized by the presence of a double bond and an oxygen atom.
- The stabilization of the intermediate is achieved by delocalization of the positive charge through resonance with the adjacent double bond and oxygen atom.

4. Formation of the Final Product:
- The stabilized intermediate, 2-hydroxy-3-methylbutene, can react further with bromine to yield the final product, 3-bromo-3-methyl-2-butanone.
- This reaction involves the addition of bromine to the double bond present in 2-hydroxy-3-methylbutene, resulting in the substitution of the hydrogen atom with a bromine atom.
- The resulting product, 3-bromo-3-methyl-2-butanone, is a ketone compound with a bromine atom attached to the carbon adjacent to the carbonyl group.

In conclusion, the unstable intermediate involved in the reaction between 2, 2-dimethyl-3-oxobutyric acid and bromine is 2-hydroxy-3-methylbutene. This intermediate is formed through the rearrangement of the initial bromonium ion intermediate and is subsequently converted into the final product, 3-bromo-3-methyl-2-butanone.
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On heating in the presence of bromine, 2, 2-dimethyl-3-oxobutyric acid produces 3-bromo-3-methyl-2-butanone. What unstable intermediate is involved in this reaction?a)1,2, 2-trimethyicyclopropanolb)2, 2-dimethyl β-butyrolactonec)2-hydroxy-3-methylbutened)dimethylketeneCorrect answer is option 'C'. Can you explain this answer?
Question Description
On heating in the presence of bromine, 2, 2-dimethyl-3-oxobutyric acid produces 3-bromo-3-methyl-2-butanone. What unstable intermediate is involved in this reaction?a)1,2, 2-trimethyicyclopropanolb)2, 2-dimethyl β-butyrolactonec)2-hydroxy-3-methylbutened)dimethylketeneCorrect answer is option 'C'. Can you explain this answer? for JEE 2024 is part of JEE preparation. The Question and answers have been prepared according to the JEE exam syllabus. Information about On heating in the presence of bromine, 2, 2-dimethyl-3-oxobutyric acid produces 3-bromo-3-methyl-2-butanone. What unstable intermediate is involved in this reaction?a)1,2, 2-trimethyicyclopropanolb)2, 2-dimethyl β-butyrolactonec)2-hydroxy-3-methylbutened)dimethylketeneCorrect answer is option 'C'. Can you explain this answer? covers all topics & solutions for JEE 2024 Exam. Find important definitions, questions, meanings, examples, exercises and tests below for On heating in the presence of bromine, 2, 2-dimethyl-3-oxobutyric acid produces 3-bromo-3-methyl-2-butanone. What unstable intermediate is involved in this reaction?a)1,2, 2-trimethyicyclopropanolb)2, 2-dimethyl β-butyrolactonec)2-hydroxy-3-methylbutened)dimethylketeneCorrect answer is option 'C'. Can you explain this answer?.
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