Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 7, Problem 7.42P
Interpretation Introduction

Interpretation:

It is to be explained why the equilibrium percentage of the first given molecule in its keto form is lower than that of the second given molecule, referring to Table 7-1.

Concept introduction:

In aqueous basic or acidic conditions, ketones and aldehydes exist in rapid equilibrium with a rearranged form called enol form. As a ketone or aldehyde, the species is called the keto form. In the enol form, the species has a carbon atom that is simultaneously a part of a C = C bond, which is a characteristic of alkenes, and is bonded to OH, which is a characteristic of alcohol. These two forms are always in equilibrium with each other, and this is called keto-enol tautomerization. For cyclic aldehydes and ketones, the percentage of keto form increases as the ring size increases. This is because the angle strain increases in small cyclic rings. The bond angle for a sp2 hybridized carbon atom is larger than it is for a sp3 hybridized carbon atom.

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Organic Chemistry: Principles and Mechanisms (Second Edition)

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