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Question:

The correct statement regarding a carbonyl compound with a hydrogen atom on its alpha carbon, is:

a carbonyl compound with a hydrogen atom on its alpha-carbon never equilibrates with its corresponding enol

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

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

a carbonyl compound with a hydrogen atom on its alpha-carbon rapidly equilibrates with its corresponding enol and this process is known as carbonylation

Solution:

The correct statement regarding a carbonyl compound with a hydrogen atom on its alpha carbon, is given by the option 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." For example, the keto enol tautomerism for acetaldehyde is as shown. CH3CHO⇌CH2=CHOH The inter conversion of the two forms (keto and enol) involves the movement of an alpha hydrogen and the shifting of bonding electrons.