Question

Arrange the following in increasing order of expected enol content : CH₃COCH₂CHO, CH₃COCH₃, CH₃CHO, CH₃COCH₂COCH₃

Answer 1

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Answer 2

Answer:

CH3CHO<CH3COCH3<CH3COCOCH3<CH3COCH2COCH3 is the correct increasing order of enol content.

Explanation:

The lower members of aldehydes and ketones formaldehyde and acetone are soluble in water.

This is because the form hydrogen bond with water.

The solubility of aldehydes and ketones decrease with increase in length of carbon chain.

Keto enol tautomerism is possible between a ketone and an aldehyde.

The keto and enol forms are tautomers of each other.

Usually, the keto form is more stable than enol form.

Enol form is stable when there is hydrogen bonding.

It is stable when there is a carbon carbon double bond.

The more substituted alkene makes the enol bond stable.

Hence, CH3CHO<CH3COCH3<CH3COCOCH3<CH3COCH2COCH3 is the correct increasing order of enol content.