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Question

The correct statement regarding a carbonyl compound with a hydrogen atom on its alpha carbon, is :
  1. a carbonyl compound with a hydrogen atom on its alpha-carbon never equilibrates with its corresponding enol
  2. a carbonyl compound with a hydrogen atom on its alpha-carbon rapidly equilibrates with its corresponding enol and this process is known as aldehyde-ketone equilibration
  3. a carbonyl compound with a hydrogen atom on its alpha-carbon rapidly equilibrates with its corresponding enol and this process is known as keto-enol tautomerism
  4. a carbonyl compound with a hydrogen atom on its alpha-carbon rapidly equilibrates with its corresponding enol and this process is known as carbonylation

A
a carbonyl compound with a hydrogen atom on its alpha-carbon rapidly equilibrates with its corresponding enol and this process is known as aldehyde-ketone equilibration
B
a carbonyl compound with a hydrogen atom on its alpha-carbon rapidly equilibrates with its corresponding enol and this process is known as carbonylation
C
a carbonyl compound with a hydrogen atom on its alpha-carbon rapidly equilibrates with its corresponding enol and this process is known as keto-enol tautomerism
D
a carbonyl compound with a hydrogen atom on its alpha-carbon never equilibrates with its corresponding enol
Solution
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The correct statement regarding a carbonyl compound with a hydrogen atom on its alpha carbon, is given by the option D.
"A carbonyl compound with a hydrogen atom on its alpha-carbon rapidly equilibrates with its corresponding enol and this process is known as keto-enol tautomerism."
For example, the keto enol tautomerism for acetaldehyde is as shown.
CH3CHOCH2=CHOH
The inter conversion of the two forms (keto and enol) involves the movement of an alpha hydrogen and the shifting of bonding electrons.

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