Explain why 92% of 2,4-pentanedione exists as the enol tautomer in hexane but only 15% of this compound exists as the enol tautomer in water. The enol tautomer can form hydrogen bonds both with hexane and water, but the keto tautomer can form hydrogen bonds with water only. Neither the keto nor the enol tautomer can form hydrogen bonds with hexane, but the keto tautomer can form a hydrogen bond with water, which stabilizes it. The keto tautomer can form hydrogen bonds both with hexane and water, but the enol tautomer can form hydrogen bonds with water only. Neither the keto nor the enol tautomer can form hydrogen bonds with hexane, but the enol tautomer can form an intramolecular hydrogen bond, which stabilizes it.

Explain why 92% of 2,4-pentanedione exists as the enol tautomer in hexane but only 15% of this compound exists as the enol tautomer in water. The enol tautomer can form hydrogen bonds both with hexane and water, but the keto tautomer can form hydrogen bonds with water only. Neither the keto nor the enol tautomer can form hydrogen bonds with hexane, but the keto tautomer can form a hydrogen bond with water, which stabilizes it. The keto tautomer can form hydrogen bonds both with hexane and water, but the enol tautomer can form hydrogen bonds with water only. Neither the keto nor the enol tautomer can form hydrogen bonds with hexane, but the enol tautomer can form an intramolecular hydrogen bond, which stabilizes it.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Concept explainers

Reactions at the Alpha Carbon Atom

The position next to the ketone or aldehyde functional group is termed as alpha position and the reaction which occurs at alpha position is called alpha substitution reaction. In an alpha substitution reaction, the alpha proton atom is substituted by an electrophile by the formation of an enol intermediate or enolate ion intermediate. Most of the carbonyl compounds go through an alpha substitution reaction.

Question

Explain why 92% of 2,4-pentanedione exists as the enol tautomer in hexane but only 15% of this compound exists as the enol tautomer in water.
The enol tautomer can form hydrogen bonds both with hexane and water, but the keto tautomer can form hydrogen bonds with water only.
Neither the keto nor the enol tautomer can form hydrogen bonds with hexane, but the keto tautomer can form a hydrogen bond with water, which stabilizes it.
The keto tautomer can form hydrogen bonds both with hexane and water, but the enol tautomer can form hydrogen bonds with water only.
Neither the keto nor the enol tautomer can form hydrogen bonds with hexane, but the enol tautomer can form an intramolecular hydrogen bond, which stabilizes it.

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