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.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter23: Addition To A Carbonyl

Section: Chapter Questions

Problem 42CTQ

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